[ CAS No. 928-90-5 ] {[proInfo.proName]}

Name: 928-90-5|5-Hexyn-1-ol|95%
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SKU: A863106
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2D 3D

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Quality Control of [ 928-90-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 928-90-5 ]

Product Details of [ 928-90-5 ]

CAS No. :	928-90-5	MDL No. :	MFCD00002980
Formula :	C₆H₁₀O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	GOQJMMHTSOQIEI-UHFFFAOYSA-N
M.W :	98.14	Pubchem ID :	70234
Synonyms :

Calculated chemistry of [ 928-90-5 ]

Physicochemical Properties

Num. heavy atoms :	7
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.67
Num. rotatable bonds :	3
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	30.28
TPSA :	20.23 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.31 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.84
Log Po/w (XLOGP3) :	0.83
Log Po/w (WLOGP) :	0.86
Log Po/w (MLOGP) :	1.39
Log Po/w (SILICOS-IT) :	1.11
Consensus Log Po/w :	1.21

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.77
Solubility :	16.5 mg/ml ; 0.169 mol/l
Class :	Very soluble
Log S (Ali) :	-0.84
Solubility :	14.3 mg/ml ; 0.145 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.92
Solubility :	11.7 mg/ml ; 0.119 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.34

Safety of [ 928-90-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 928-90-5 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 928-90-5 ]
Downstream synthetic route of [ 928-90-5 ]

[ 928-90-5 ] Synthesis Path-Upstream 1~24

1
[ 18420-41-2 ]
[ 928-90-5 ]

Yield	Reaction Conditions	Operation in experiment
67%	for 4 h; Cooling	To about 100 mL of liquid ammonia stirred at -40 °C, a small amount of iron(III) nitrate nonahydrate were added. Then, sodium (85.3 g, 3.72 mol) was added by small portions. After confirmation of sodium amide formation by changing color from deep blue to gray, 5 was added dropwise for 1 h and the mixture was further stirred for 3 h. After removing the cool bath, nitrogen was flowed to promote evaporation of ammonia, and water was added dropwise at ambient temperature. The mixture was extracted with diethyl ether and the combined organic layer was dried over anhydrous magnesium sulfate. After filtration, solvent in the filtrate was removed under reduced pressure, and vacuum distillation of the residue gave 53.8 g (67 percent) of 6 as colorless oil

Reference： [1] Tetrahedron Letters, 2005, vol. 46, # 38, p. 6449 - 6451
[2] Tetrahedron, 1986, vol. 42, # 7, p. 2017 - 2024
[3] Bulletin of the Chemical Society of Japan, 2017, vol. 90, # 3, p. 298 - 305
[4] Journal of the Chemical Society, 1952, p. 2873,2880
[5] Helvetica Chimica Acta, 1977, vol. 60, p. 1161 - 1174
[6] Journal of Organic Chemistry, 1974, vol. 39, p. 3378 - 3384
[7] Journal of the American Chemical Society, 1983, vol. 105, # 12, p. 4008 - 4017
[8] Tetrahedron Letters, 1994, vol. 35, # 4, p. 641 - 644
[9] Tetrahedron, 1998, vol. 54, # 15, p. 3929 - 3934
[10] Bulletin of the Chemical Society of Japan, 2017, vol. 90, # 4, p. 387 - 394

2
[ 123186-35-6 ]
[ 928-90-5 ]

Yield	Reaction Conditions	Operation in experiment
72%	at 20℃; for 18 h; Green chemistry	General procedure: To a Reacti-vial (Thermo Scientific) containing the 4-methoxybenzyl protected alcohol (1mmol) were added sodium nitrite (3–10 molpercent), glacial acetic acid (1mL) and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (1.5–5 molpercent). The resulting mixture was stirred at room temperature under an atmosphere of oxygen for 18 h. The solution was then evaporated under reduced pressure and the residue purified by flash chromatography.

Reference： [1] RSC Advances, 2013, vol. 3, # 34, p. 14814 - 14828
[2] Tetrahedron, 2014, vol. 70, # 40, p. 7380 - 7387

3
[ 18343-91-4 ]
[ 928-90-5 ]
[ 69441-76-5 ]

Reference： [1] Patent: US2013/96295, 2013, A1, . Location in patent: Paragraph 0056

4
[ 73448-13-2 ]
[ 928-90-5 ]

Reference： [1] Tetrahedron Letters, 1985, vol. 26, # 44, p. 5393 - 5396

5
[ 53293-00-8 ]
[ 928-90-5 ]

Reference： [1] Journal of the American Chemical Society, 2011, vol. 133, # 49, p. 19976 - 19981
[2] Patent: US2002/49244, 2002, A1,

6
[ 764-60-3 ]
[ 928-90-5 ]

Reference： [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 22, p. 6572 - 6576[2] Angew. Chem., 2018, vol. 130, p. 6682 - 6686,5
[3] Synthesis, 1998, # 7, p. 1015 - 1018
[4] Chemical Communications, 2011, vol. 47, # 31, p. 8832 - 8834

7
[ 100-72-1 ]
[ 928-90-5 ]

Reference： [1] Journal of the American Chemical Society, 2000, vol. 122, # 46, p. 11348 - 11357
[2] Tetrahedron Letters, 2005, vol. 46, # 38, p. 6449 - 6451
[3] Tetrahedron, 1998, vol. 54, # 15, p. 3929 - 3934
[4] Tetrahedron Letters, 1994, vol. 35, # 4, p. 641 - 644
[5] Tetrahedron, 1986, vol. 42, # 7, p. 2017 - 2024
[6] Journal of the Chemical Society, 1952, p. 2873,2880
[7] Bulletin of the Chemical Society of Japan, 2017, vol. 90, # 3, p. 298 - 305
[8] Bulletin of the Chemical Society of Japan, 2017, vol. 90, # 4, p. 387 - 394

8
[ 1720-37-2 ]
[ 928-90-5 ]

Reference： [1] Synthetic Communications, 1999, vol. 29, # 16, p. 2807 - 2815
[2] Tetrahedron Letters, 1985, vol. 26, # 44, p. 5393 - 5396
[3] Phosphorus, Sulfur and Silicon and Related Elements, 2001, vol. 171-172, p. 167 - 172

9
[ 77758-51-1 ]
[ 762-72-1 ]
[ 928-90-5 ]

Reference： [1] European Journal of Organic Chemistry, 2010, # 18, p. 3382 - 3386

10
[ 128217-23-2 ]
[ 928-90-5 ]

Reference： [1] Journal of Organic Chemistry, 2009, vol. 74, # 5, p. 2067 - 2074

11
[ 128217-23-2 ]
[ 928-90-5 ]
[ 123171-29-9 ]

Reference： [1] Journal of Organic Chemistry, 2009, vol. 74, # 5, p. 2067 - 2074

12
[ 4221-03-8 ]
[ 90965-06-3 ]
[ 928-90-5 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 5, p. 1419 - 1427

13
[ 68274-83-9 ]
[ 928-90-5 ]

Reference： [1] Helvetica Chimica Acta, 1978, vol. 61, p. 2275 - 2285

14
[ 77758-51-1 ]
[ 928-90-5 ]

Reference： [1] Journal of the American Chemical Society, 1980, vol. 102, p. 1333

15
[ 77566-25-7 ]
[ 928-90-5 ]
[ 29329-03-1 ]
[ 77566-35-9 ]

Reference： [1] Bulletin de la Societe Chimique de France, 1980, vol. 2, # 7-8, p. 374 - 380

16
[ 13392-69-3 ]
[ 928-90-5 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 5, p. 1419 - 1427

17
[ 187756-41-8 ]
[ 928-90-5 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 5, p. 1419 - 1427

18
[ 5622-76-4 ]
[ 69284-62-4 ]
[ 928-90-5 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 2008, vol. 81, # 8, p. 1028 - 1037

19
[ 1002-28-4 ]
[ 928-90-5 ]

Reference： [1] Journal of the Chemical Society, Chemical Communications, 1976, p. 959 - 960

20
[ 17889-21-3 ]
[ 928-90-5 ]

Reference： [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1964, p. 871 - 872[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1964, # 5, p. 931 - 932

21
[ 928-90-5 ]
[ 10297-06-0 ]

Reference： [1] Molecular Crystals and Liquid Crystals Science and Technology Section A: Molecular Crystals and Liquid Crystals, 2002, vol. 377, p. 13 - 18

22
[ 928-90-5 ]
[ 2468-56-6 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 1, p. 116 - 125
[2] Journal of the American Chemical Society, 2014, vol. 136, # 16, p. 5821 - 5823
[3] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1994, # 15, p. 2181 - 2186
[4] Organic Letters, 2018, vol. 20, # 3, p. 788 - 791
[5] Chemistry - A European Journal, 2017, vol. 23, # 71, p. 17862 - 17866
[6] Organic Letters, 2011, vol. 13, # 4, p. 660 - 663
[7] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1990, # 11, p. 2909 - 2918
[8] Patent: US2014/335018, 2014, A1,
[9] Angewandte Chemie - International Edition, 2016, vol. 55, # 2, p. 649 - 653[10] Angew. Chem., 2016, vol. 128, # 2, p. 659 - 663,5

23
[ 928-90-5 ]
[ 96289-13-3 ]
[ 6968-11-2 ]

Reference： [1] RSC Advances, 2015, vol. 5, # 67, p. 54301 - 54303

24
[ 928-90-5 ]
[ 151978-58-4 ]

Reference： [1] Organic Letters, 2015, vol. 17, # 7, p. 1754 - 1757

[ 928-90-5 ] Synthesis Path-Downstream 1~88

1
[ 928-90-5 ]
[ 53293-00-8 ]

Yield	Reaction Conditions	Operation in experiment
82%	With jones' reagent In acetone for 1h; Ambient temperature;
80%	With chromium(VI) oxide; hydrogen cation In acetone
76%	With jones reagent at 0℃;

71%	With Jones reagent In acetone at 0 - 20℃;
68%	With jones reagent
67%	With jones reagent In acetone for 0.5h; Ambient temperature;
67%	With Jones reagent In acetone at 0 - 20℃;
	With chromium(VI) oxide; sulfuric acid; acetone
	With Jones reagent (CrO₃*H₂SO₂) In acetone Ambient temperature;
	With jones' reagent In acetone at 0℃;
	With jones reagent
	With Jones reagent In acetone at 0 - 5℃; for 2h;	General procedures for the synthetic compounds General procedure: 3.2.1. Compound 3: To a solution of 5-hexyn-1-ol (l.5 g,15.3 mmol) in acetone (25 ml) at 08C wasadded dropwise a solution of Jonesreagents (30 ml), and the mixture wasallowed to warm to room temperature.Water was added, and the resulting mixturewas extracted with ether, washed successivelywith water and brine, dried(MgSO4), and the solvent was concentratedto half. A freshly prepared solution ofCH2N2 in Et2O was added dropwise to theacid until the solution remained paleyellow and no more N2 was evolved. Themixture was washed with NaOH solutionand H2O, dried (MgSO4), and evaporated.The residue was subjected to flash chromatographyto give the title compound 3(1.6 g, 85%yield) as colorless oil. 1HNMR(CDCl3, 400MHz): d (ppm) 1.85 (m, 2H,H-3), 1.95 (t, 1H, J 2.1 Hz, H-6), 2.24(dt, 2H, J 7.2, 2.1 Hz, H-4), 2.47 (t, 2H,J 7.2 Hz, H-2), 3.67 (s, 3H, OCH3).

Reference： [1]Earl; Vollhardt [Journal of Organic Chemistry, 1984, vol. 49, # 25, p. 4786 - 4800]
[2]Jeffery [Tetrahedron Letters, 1993, vol. 34, # 7, p. 1133 - 1136]
[3]Corey, E. J.; Su, Wei-guo [Tetrahedron Letters, 1984, vol. 25, # 45, p. 5119 - 5122]
[4]Location in patent: experimental part Proteau-Gagne; St-Jean; Morin; Gendron; Rousseau; Dory [Chemistry of Natural Compounds, 2011, vol. 46, # 6, p. 841 - 847]
[5]Millar, Jocelyn G.; Oehlschlager, Allan C. [Journal of Organic Chemistry, 1984, vol. 49, # 13, p. 2332 - 2338]
[6]Moody, Christopher J.; Shah, Pritom; Knowles, Philip [Journal of the Chemical Society. Perkin transactions I, 1988, p. 3249 - 3254]
[7]Bertrand, Helene C.; Clede, Sylvain; Guillot, Regis; Lambert, Francois; Policar, Clotilde [Inorganic Chemistry, 2014, vol. 53, # 12, p. 6204 - 6223]
[8]Eglinton; Whiting [Journal of the Chemical Society, 1953, p. 3052,3055]
[9]Delorme; Girard; Rokach [Journal of Organic Chemistry, 1989, vol. 54, # 15, p. 3635 - 3640]
[10]Yadav, J. S.; Vadapalli, Prahlad [Tetrahedron Letters, 1994, vol. 35, # 4, p. 641 - 644]
[11]Durand, Sandrine; Parrain, Jean-Luc; Santelli, Maurice [Synthesis, 1998, # 7, p. 1015 - 1018]
[12]Gong, Jing-Xu; Wang, He-Yao; He, Wen-Fei; Wang, Zhen-Zhong; Xiao, Wei; Guo, Yue-Wei [Journal of Asian Natural Products Research, 2013, vol. 15, # 8, p. 916 - 919]

2
[ 928-90-5 ]
[ 615-42-9 ]
[ 151860-00-3 ]

Yield	Reaction Conditions	Operation in experiment
62%	With copper(l) iodide; N-butylamine In diethyl ether at 20℃; for 4h;
50%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine at 60℃; for 12h; Inert atmosphere;	6.B To a solution of Pd(PPh3)4 (3 mol%, 350 mg) and Cul (5 mol%, 100 mg) in Et3N (40 mL) under an argon atmosphere was added a solution of 1 ,2-diiodobenzene (10 mmol, 3.3 g) and 5- hexyne-1-ol (10 mmol, 980 mg) in Et3N (10 mL). The reaction was heated to 60 °C for 12 h, then cooled to rt and filtered through a pad of Celite. The filtrate was concentrated in vacuo and the residue was purified using a Teledyne Isco Combiflash RF chromatographic system [40 g Si02 column eluted with EtOAc/hexanes (1 :2)] to give 19 (1.5 g, 50%) as a pale yellow oil. TLC: EtOAc/hexanes (1 :2), Rf ~ 0.2. 1H NMR (500 MHz, CDCl3) δ 1.73 - 1.81 (m, 2H), 1.82 - 1.88 (m, 2H), 2.55 (t, J = 7.0 Hz, 2H), 3.76 (t, J = 7.0 Hz, 2H), 6.98 (dd, J = 7.0, 8.0 Hz, 1 H), 7.29 (dd, J = 7.0, 8.0 Hz, 1 H), 7.42 (d, J = 7.5 Hz, 1 H), 7.84 (d, J = 8.0 Hz, 1 H).
50%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine at 60℃; for 12h; Inert atmosphere;	6. B Step B. To a solution of Pd(PPh3)4 (3 mol %, 350 mg) and CuI (5 mol %, 100 mg) in Et3N (40 mL) under an argon atmosphere was added a solution of 1,2-diiodobenzene (10 mmol, 3.3 g) and 5-hexyne-1-ol (10 mmol, 980 mg) in Et3N (10 mL). The reaction was heated to 60° C. for 12 h, then cooled to rt and filtered through a pad of Celite. The filtrate was concentrated in vacuo and the residue was purified using a Teledyne Isco Combiflash RF chromatographic system [40 g SiO2 column eluted with EtOAc/hexanes (1:2)] to give 19 (1.5 g, 50%) as a pale yellow oil. (0244) TLC: EtOAc/hexanes (1:2), Rf0.2. 1H NMR (500 MHz, CDCl3) δ 1.73-1.81 (m, 2H), 1.82-1.88 (m, 2H), 2.55 (t, J=7.0 Hz, 2H), 3.76 (t, J=7.0 Hz, 2H), 6.98 (dd, J=7.0, 8.0 Hz, 1H), 7.29 (dd, J=7.0, 8.0 Hz, 1H), 7.42 (d, J=7.5 Hz, 1H), 7.84 (d, J=8.0 Hz, 1H).

50%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine at 60℃; for 12h; Inert atmosphere;
48%	With copper(l) iodide; triethylamine In tetrahydrofuran Ambient temperature;
	With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine 1.) 10 min, 2.) overnight; Yield given. Multistep reaction;

Reference： [1]Lo, Yu-Hsiang; Lin, I-Ling; Lin, Chi-Fong; Hsu, Cheng-Chung; Yang, Sheng-Huei; Lin, Shinne-Ren; Wu, Ming-Jung [Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 13, p. 4528 - 4536]
[2]Current Patent Assignee: THE UNIVERSITY OF TEXAS SYSTEM; Helmholtz Association - WO2015/110262, 2015, A1 Location in patent: Page/Page column 63; 64
[3]Current Patent Assignee: THE UNIVERSITY OF TEXAS SYSTEM; Helmholtz Association - US2017/8918, 2017, A1 Location in patent: Paragraph 0242-0244
[4]Adebesin, Adeniyi Michael; Wesser, Tim; Vijaykumar, Jonnalagadda; Konkel, Anne; Paudyal, Mahesh P.; Lossie, Janine; Zhu, Chen; Westphal, Christina; Puli, Narender; Fischer, Robert; Schunck, Wolf-Hagen; Falck, John R. [Journal of Medicinal Chemistry, 2019, vol. 62, # 22, p. 10124 - 10143]
[5]Grissom, Janet Wisniewski; Klingberg, Detlef [Journal of Organic Chemistry, 1993, vol. 58, # 24, p. 6559 - 6564] Grissom, Janet Wisniewski; Klingberg, Detlef; Meyenburg, Sabine; Stallman, Brenda L. [Journal of Organic Chemistry, 1994, vol. 59, # 25, p. 7876 - 7888]
[6]Grissom, Janet Wisniewski; Calkins, Trevor L.; Egan, Miles [Journal of the American Chemical Society, 1993, vol. 115, # 25, p. 11744 - 11752]

3
[ 928-90-5 ]
[ 2468-56-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 116 - 125
[2]Journal of the American Chemical Society,2014,vol. 136,p. 5821 - 5823
[3]Journal of the Chemical Society. Perkin transactions I,1994,p. 2181 - 2186
[4]Organic Letters,2018,vol. 20,p. 788 - 791
[5]Chemistry - A European Journal,2017,vol. 23,p. 17862 - 17866
[6]Organic Letters,2011,vol. 13,p. 660 - 663
[7]Journal of the Chemical Society. Perkin transactions I,1990,p. 2909 - 2918
[8]Patent: US2014/335018,2014,A1
[9]Angewandte Chemie - International Edition,2016,vol. 55,p. 649 - 653
Angew. Chem.,2016,vol. 128,p. 659 - 663,5
[10]Journal of Organic Chemistry,2020,vol. 85,p. 3717 - 3727
[11]European Journal of Medicinal Chemistry,2020,vol. 200

4
[ 928-90-5 ]
[ 66977-99-9 ]

Yield	Reaction Conditions	Operation in experiment
99%	With carbon tetrabromide; triphenylphosphine In dichloromethane at 20℃; for 1h; Inert atmosphere;
87%	With bromine; triphenylphosphine In acetonitrile at 0℃;
65%	With carbon tetrabromide; triphenylphosphine In diethyl ether for 1h; Ambient temperature;

60%	With carbon tetrabromide; triphenylphosphine In dichloromethane at 0 - 20℃; Inert atmosphere;
	With phosphorus tribromide In diethyl ether at -5℃; for 2h; Yield given;
	With carbon tetrabromide; triphenylphosphine
	Multi-step reaction with 2 steps 1: dmap; triethylamine / dichloromethane / 15 h / 20 °C 2: lithium bromide / N,N-dimethyl-formamide / 24 h / 20 °C
	Multi-step reaction with 2 steps 1: dmap; triethylamine / dichloromethane / 15 h / 0 - 20 °C 2: lithium bromide / N,N-dimethyl-formamide / 24 h / 20 °C

Reference： [1]Coombs, John R.; Zhang, Liang; Morken, James P. [Journal of the American Chemical Society, 2014, vol. 136, # 46, p. 16140 - 16143]
[2]Coleman, Robert S.; Garg, Rahul [Organic Letters, 2001, vol. 3, # 22, p. 3487 - 3490]
[3]Schill, Gottfried; Schweickert, Norbert; Fritz, Hans; Vetter, Walter [Chemische Berichte, 1988, vol. 121, p. 961 - 970]
[4]Villemin, Elise; Herent, Marie-France; Marchand-Brynaert, Jacqueline [European Journal of Organic Chemistry, 2012, # 31, p. 6165 - 6178]
[5]Sharma, Sunaina; Oehlschlager, Allan C. [Journal of Organic Chemistry, 1989, vol. 54, # 21, p. 5064 - 5073]
[6]Wang, Xueqiang; Liu, Yu; Martin, Ruben [Journal of the American Chemical Society, 2015, vol. 137, # 20, p. 6476 - 6479]
[7]Junker, Anna; Balasubramanian, Ramachandran; Ciancetta, Antonella; Uliassi, Elisa; Kiselev, Evgeny; Martiriggiano, Chiara; Trujillo, Kevin; Mtchedlidze, Giorgi; Birdwell, Leah; Brown, Kyle A.; Harden, T. Kendall; Jacobson, Kenneth A. [Journal of Medicinal Chemistry, 2016, vol. 59, # 13, p. 6149 - 6168]
[8]Current Patent Assignee: GOVERNMENT OF THE UNITED STATES - WO2017/53769, 2017, A1

5
[ 928-90-5 ]
[ 94398-27-3 ]
[ 126542-63-0 ]

Yield	Reaction Conditions	Operation in experiment
	In 1,4-dioxane for 5h; Heating; Yield given;

Reference： [1]Neunhoeffer, Hans; Reichel, Diethard; Cullmann, Birgit; Rehn, Ingrid [Liebigs Annalen der Chemie, 1990, # 7, p. 631 - 640]

6
[ 928-90-5 ]
[ 124-63-0 ]
[ 79496-61-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	With triethylamine; In dichloromethane; at 0℃;	Methanesulfonyl chloride (14.3 mL, 184 mmol) was added toa solution of hex-5-yn-1-ol (15 g, 153 mmol) and triethylamine (33.2 mL, 230 mmol) in drydichloromethane (300 mL) at 0 C. The mixture was stirred overnight, then washed with water (1x 140 mL), 1 M hydrochloric acid (1 x 120 mL), a 5% aqueous solution of sodium bicarbonate (1x 120 mL), and brine (1 x 120 mL). The organic phase was dried over anhydrous sodium sulfate,filtered, and evaporated, giving hex-5-yn-1-yl methanesulfonate; yield: 26.8 g (100 %); 1H NMRspectrum corresponds with data in literature [4].
98%	With triethylamine; In dichloromethane; at 0 - 20℃; for 14h;Inert atmosphere;	To a flame dried, round bottom flask equipped with a magnetic stir bar was added hex-5-yn-1-ol (500 mg,5.09 mmol), dry CH2Cl2 (50 mL), and triethylamine (618.3 mg, 6.11 mmol). The reaction mixture was cooled to 0oC, and methanesulfonyl chloride (641.9 mg, 5.60 mmol) was added dropwise under argon. The reaction mixturewas then allowed to warm to room temperature and stirred for 14 hours. Then, 0.05 M HCl (20 mL) was added andthe layers were separated. The organic layer was washed with sat. NaHCO3 (20 mL), dried over MgSO4, andconcentrated under vacuum to obtain a pale yellow liquid (881.2 mg, 98%), which was used further withoutpurification.
93%	With triethylamine; In tetrahydrofuran; at 0 - 20℃; for 3h;	General procedure: To a solution of 9a (5.85 g, 33 mmol) and Et3N (5.85 mL, 42 mmol) in THF (95 mL) was added MsCl (2.6 mL, 33.6 mmol) at 0 C, and the mixture was stirred at room temperature for 2 h. The reaction was quenched with water (84 mL), and the separated aqueous layer was extracted with EtOAc (150 + 75 + 75 mL). The combined organic layers were washed with 10% HCl aq (50 mL), satd NaHCO3 aq (50 mL), brine (50 mL), dried over Na2SO4, and concentrated. Column chromatography (SiO2 200 g, hexane/EtOAc 4/1 to 3/2) gave 10a (7.77 g, E/Z 9/1, 93%) as a colorless oil.

89%	With triethylamine; In dichloromethane; at 0℃; for 3h;	To a solution of hex-5-yn-1-ol (2.00 g, 20.4 mmol, CAS928-90-5) and TEA (5.16 g, 51.0 mmol) in DCM (20 mL) was added MsCl (2.80 g, 24.5 mmol) at 0 C. The reaction mixture was stirred at 0 C. for 3 hrs. On completion, the mixture was quenched with water (20 mL), and extracted with DCM (2×20 mL). The organic layer was washed with brine (50 mL), dried with Na2SO4, filtered and the filtrate was concentrated in vacuo to give the title compound (3.20 g, 89% yield) as yellow oil. 1H NMR (400 MHz, CDCl3) delta 4.27 (t, J=6.4 Hz, 2H), 3.02 (s, 3H), 2.30-2.24 (m, 2H), 1.98 (t, J=2.8 Hz, 1H), 1.93-1.84 (m, 2H), 1.70-1.64 (m, 2H).
	With triethylamine; In dichloromethane;	(i) A solution of methanesulphonyl chloride (23.7 ml) in dry dichloromethane (25 ml.) was added dropwise to a solution of hex-5-yn-1-ol (Lancaster Synthesis, 25 g) and triethylamine (47.3 ml) in dichloromethane (300 ml), and stirred under a nitrogen atmosphere at -70. The resulting mixture was allowed to warm to room temperature over 16 hours. The mixture was then washed with water, dilute hydrochloric acid, saturated sodium bicarbonate solution and brine before drying over anhydrous magnesium sulphate and evaporation in vacuo. Hex-5-ynyl methanesulphonate was obtained as an oil (43.6 g) and was used without purification.
	With triethylamine; In dichloromethane;	(i) A solution of methanesulphonyl chloride (23.7 ml) in dry dichloromethane (25 ml.) was added dropwise to a solution of hex-5-yn-1-ol (Lancaster Synthesis, 25 g) and triethylamine (47.3 ml) in dichloromethane (300 ml), stirred under a nitrogen atmosphere at -70. The resulting mixture was allowed to warm to room temperature over 16 hours. The mixture was then washed with water, dilute hydrochloric acid, saturated sodium bicarbonate solution and brine before drying over anhydrous magnesium sulphate and evaporation in vacuo. Hex-5-ynyl methanesulphonate was obtained as an oil (43.6 g) and was used without purification. Nuclear magnetic resonance spectrum (NMR) was as follows: 1 H (p.p.m from TMS in CDCl3, integral, number of peaks, JHz): 4.15, 2H, t, JHz 6; 3.0, 3H, s; 2.4-1.4, 7H, m.
	With triethylamine; In diethyl ether; at 0℃; for 1h;	Example 17 hex-5-ynyl methanesulfonate (17b) To a solution of 2.3 ml of hexynol 17a, in 15 ml of diethyl ether was added 3 ml of triethyl amine, followed by 1.6 ml of mesyl chloride at 0 C. The mixture was stirred for 1 hr at 0 C., then diluted with 20 ml of water and extracted with diethyl ether. The extract was washed with 1N NaOH, water, dried and concentrated, to give 3.5 g of mesylate 17b as a colorless oil. Rf 0.65 (heptane/acetone 1/1). NMR (CDCl3) delta 1.90 (m, 2, CH2), 1.98 (t, 1, acetylene-H), 2.28 (dt, 2, CH2), 4.28 (t, 2, CH2), 3.02 (s, 3, OSO2CH3).
	With triethylamine; In diethyl ether; at 0℃; for 1h;	To a solution of 2.3 ml of hexynol 17a, in 15 ml of diethyl ether was added 3 ml of triethyl amine, followed by 1.6 ml of mesyl chloride at O0C. The mixture was stirred for 1 hr at O0C, then diluted with 20 ml of water and extracted with diethyl ether. The extract was washed with IN NaOH, water, dried and concentrated, to give 3.5 g of mesylate 17b as a colorless oil. Rf 0.65 (heptane/acetone 1/1).NMR(CDCl3) delta 1.90 (m, 2, CH2), 1.98 (t, 1, acetylene-H), 2.28 (dt, 2, CH2), 4.28 (t, 2, CH2), 3.02 (s, 3, OSO2CH3).
	With triethylamine; In dichloromethane; at 0 - 20℃;	To a vigorously stirred solution of 5-hexyn-1-ol (4 mmol) and triethylamine (4.5 mmol) in dichloromethane (DCM) (100 mL), methylsulfonyl chloride (MsCl) (4.1 mmol in DCM) is added dropwise at 0 C. The mixture is then warmed to room temperature for stirring overnight. Sodium bicarbonate (aqueous) is poured into the reaction mixture and the organic phase is separated. The aqueous layer is extracted with DCM and the combined organic extracts are washed with water and brine, dried over magnesium sulfate (MgSO4) and the solvent evaporated. The crude mesylate is purified by flash column chromatography (20% ethyl acetate in n-hexane) to yield colorless oil.
	With triethylamine; In dichloromethane; at 20℃; for 2.5h;Cooling with ice; Inert atmosphere;	To a ice chilled solution of 5-hexyn-1-ol (4.77 g, 48.57 mmol) and triethylamine (13.6 mL,97.14 mmol) in dichloromethane (80 mL) was slowly added solution of methanesulfonyl chloride(6.68 g, 58.28 mmol) in dichloromethane (40 mL). The resulting solution was aged first for 30 min inice bath and then brought to ambient temperature for another 2 h. The reaction solution was washed sequentially with citric acid (10 wt %, 3 15 mL), sodium bicarbonate (10 wt %, 3 15 mL), then driedover Na2SO4. After filtration, the solvent was removed under reduced pressure to afford high purityproduct (8.47 g, quantitative yield) with no need for further purification.

Reference： [1]European Journal of Medicinal Chemistry,2020,vol. 200
[2]Tetrahedron,2008,vol. 64,p. 3578 - 3588
[3]Chem,2018,vol. 4,p. 124 - 137
[4]Journal of the Chemical Society. Perkin transactions I,1981,p. 2106 - 2115
[5]Tetrahedron,2018,vol. 74,p. 5309 - 5318
[6]Journal of the Chinese Chemical Society,2008,vol. 55,p. 668 - 674
[7]Organic and Biomolecular Chemistry,2010,vol. 8,p. 2164 - 2173
[8]Patent: US2019/192668,2019,A1 .Location in patent: Paragraph 2779; 2780
[9]Chemistry of Materials,2018,vol. 30,p. 3618 - 3622
[10]Journal of the American Chemical Society,2008,vol. 130,p. 13400 - 13409
[11]Angewandte Chemie - International Edition,2014,vol. 53,p. 3854 - 3858
Angew. Chem.,2014,vol. 126,p. 3934 - 3939,5
[12]Journal of Organic Chemistry,1991,vol. 56,p. 1807 - 1812
[13]Patent: US5026874,1991,A
[14]Patent: US5116862,1992,A
[15]Journal of the American Chemical Society,2008,vol. 130,p. 16502 - 16503
[16]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 6588 - 6590
[17]Chemistry - A European Journal,2010,vol. 16,p. 12303 - 12306
[18]Patent: US2011/28450,2011,A1 .Location in patent: Page/Page column 49-50
[19]Patent: WO2011/12600,2011,A1 .Location in patent: Page/Page column 103-104
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[21]Organic Letters,2011,vol. 13,p. 3450 - 3453
[22]Beilstein Journal of Organic Chemistry,2011,vol. 7,p. 1379 - 1386
[23]Organic Letters,2012,vol. 14,p. 3233 - 3235
[24]Green Chemistry,2013,vol. 15,p. 1962 - 1966
[25]Patent: US2014/335018,2014,A1 .Location in patent: Paragraph 0075
[26]Journal of the American Chemical Society,2016,vol. 138,p. 13076 - 13081
[27]Molecules,2016,vol. 21
[28]Organic Letters,2018,vol. 20,p. 2649 - 2653

7
[ 928-90-5 ]
[ CAS Unavailable ]
[ 121-46-0 ]
[ 163295-33-8 ]

Yield	Reaction Conditions	Operation in experiment
97%	With (η4-cyclooctadiene-1,5)(η5-indenyl)cobalt In 1,2-dimethoxyethane at 100℃; for 40h;

Reference： [1]Lee, Bun Yeoul; Chung, Young Keun; Jeong, Nakcheol; Lee, Youngshin; Hwang, Sung Hee [Journal of the American Chemical Society, 1994, vol. 116, # 19, p. 8793 - 8794]

8
[ 591-50-4 ]
[ 928-90-5 ]
[ 69936-53-4 ]

Yield	Reaction Conditions	Operation in experiment
99%	With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine at 20℃; for 12h; Inert atmosphere;
99%	With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine at 20℃; for 18h; Inert atmosphere;
99%	With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine at 20℃; Inert atmosphere;	Representative procedure: preparation of 1a General procedure: A round-bottomed flask containing a magentic stirbar and iodobenzene (911.5 mg, 4.468 mmol,1.0 equiv) was added with PdCl2(PPh3)2 (62.9 mg, 0.0896 mmol, 0.02 equiv), CuI (34.9 mg, 0.183mmol, 0.04 equiv) and 5.0 mL of Et3N. The resulted mixture was thoroughly degassed by a steadystream of argon for 15 min before propargyl alcohol (0.14 mL, 270.2 mg, 4.820 mmol, 1.1 equiv)was added via syringe. Ther resulted reaction mixture was allowed to stir at room temperatureunder argon overnight. The reaction mixture was diluted with saturated aqueous NH4Cl and theseparated aqueous layer was extracted with 3xEtOAc. Combined organic phases were washed withsaturated aqueous NaCl, dried over anhydrous Na2SO4, filtered and concentrated in vacuo to givea crude material. The crude material was purified by SiO2 column chromatography eluting with10% EtOAc-hexane to give the desired product 1a as a brown oil (451.5 mg, 76%);.

98%	With copper (I) iodide; tetrakis-(triphenylphosphine)-palladium; di-i-propyl amine In tetrahydrofuran at 20℃;
98%	With triethylamine at 50℃;
96%	With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine In dichloromethane at 20℃; for 12h; Inert atmosphere;	6-phenylhex-5-yn-1-ol S6a. A dried 100 ml round-bottomed flask was charged iodobenzene (S6) (1.000 g, 4.90 mmol), PdCl2[P(C6H5)3]2 (103.2 mg, 0.15 mmol, 3.0 mol%), CuI (28.0 mg, 0.15 mmol, 3 mol%) under argon atmosphere, 5-hexyn-1-ol (0.82 mL, 7.35 mmol) was injected, then CH2Cl2/Et3N (30 ml/5 ml) was added, the resultant solution was stirred at room temperature for 12 hours. 1M hydrochloric acid solution was added and mixture extracted with dichloromethane. The combined organic layer was washed with water and dried over MgSO4. Solvent was removed by rotary evaporator after filtration. The residue was purified by column chromatography using a mixture of ethyl acetate/hexane (1/1) and furnished the product 6-phenylhex-5-yn-1-ol (S6a) (0.903 g, 96%) as white solids. 1H NMR (400 MHz, CDCl3): δ = 1.74-1.61 (m, 4H), 2.41 (t, J = 7.2 Hz, 2H), 2.62 (bs, 1H), 3.64 (t, J = 6.4 Hz, 2H), 7.28-7.21 (m, 3H), 7.40-7.37 (m, 2H). ; 13C NMR (CDCl3, 100 MHz) δ = 19.0, 24.8, 62.0, 80.7, 89.8, 123.7, 127.4, 128.0, 131. ; HRMS (ESI, m/z) for C12H14ONa [(M+Na)+], calcd: 197.0942, found: 197.0941.
95%	With copper (I) iodide; triethylamine at 20℃;
95%	With copper (I) iodide; tetrakis-(triphenylphosphine)-palladium; triethylamine Inert atmosphere;
92%	With tetrabutylammonium hydrogensulfate; triethylamine; triphenylphosphine In water monomer; acetonitrile at 25℃; for 1.5h;
92%	With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine at 20℃; for 24h;
87%	With copper (I) iodide; tetrakis-(triphenylphosphine)-palladium; triethylamine at 50℃; for 1.5h;
86%	With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine at 20℃; for 12h;
81%	With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine at 23℃; for 17h; Inert atmosphere;
77%	With copper (I) iodide; triethylamine for 12h;
77%	With copper (I) iodide; tetrakis-(triphenylphosphine)-palladium; triethylamine In tetrahydrofuran at 20℃; for 15h;
72%	With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine In tetrahydrofuran at 20℃; Inert atmosphere;
69%	With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine In tetrahydrofuran at 65℃; Inert atmosphere; Schlenk technique;
67%	Stage #1: iodobenzene With copper (I) iodide; tetrakis-(triphenylphosphine)-palladium; triethylamine at 20℃; for 0.5h; Stage #2: 5-hexyl-1-ol at 60℃; for 18h;
29%	With 1,2-bis(thiophen-2-ylethynyl)benzene; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); triethylamine In acetonitrile at 20℃; for 17h; Inert atmosphere;
	With triethylamine at 60℃;
	With di-i-propyl amine
	With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine In acetonitrile at 40℃;
	With copper (I) iodide; tetrakis-(triphenylphosphine)-palladium; triethylamine In tetrahydrofuran at 20℃; Inert atmosphere;
	Stage #1: iodobenzene; 5-hexyl-1-ol With diethylamine In benzene Schlenk technique; Inert atmosphere; Stage #2: With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide In benzene at 20℃; Schlenk technique; Inert atmosphere;
	With piperidine; [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide In toluene at 20℃; for 2h;
	With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine at 20℃; for 12h;
	With copper (I) iodide; tetrakis-(triphenylphosphine)-palladium; triethylamine In tetrahydrofuran at 23 - 25℃; for 12h; Inert atmosphere;

Reference： [1]Chenniappan, Vinoth Kumar; Rahaim, Ronald J. [Organic Letters, 2016, vol. 18, # 19, p. 5090 - 5093]
[2]Gauthier, Raphaël; Mamone, Marius; Paquin, Jean-François [Organic Letters, 2019, vol. 21, # 22, p. 9024 - 9027]
[3]Chaisan, Nattawadee; Ruchirawat, Somsak; Ruengsangtongkul, Sureeporn; Thongsornkleeb, Charnsak; Tummatorn, Jumreang [Synlett, 2022]
[4]Mahandru, Gireesh M.; Skauge, Andy R. L.; Chowdhury, Sanjoy K.; Amarasinghe, Kande K. D.; Heeg, Mary Jane; Montgomery, John [Journal of the American Chemical Society, 2003, vol. 125, # 44, p. 13481 - 13485]
[5]Roesch; Larock [Journal of Organic Chemistry, 2001, vol. 66, # 2, p. 412 - 420]
[6]Lee, Kyu Hwan; Jillella, Raveendra; Kim, Jaewoong; Oh, Chang Ho [Bulletin of the Korean Chemical Society, 2018, vol. 39, # 5, p. 651 - 656]
[7]Patil, Nitin T.; Lutete, Leopold Mpaka; Wu, Huanyou; Pahadi, Nirmal K.; Gridnev, Ilya D.; Yamamoto, Yoshinori [Journal of Organic Chemistry, 2006, vol. 71, # 11, p. 4270 - 4279]
[8]Hsieh, Hsin-Yu; Lee, Wen-Chun; Senadi, Gopal Chandru; Hu, Wan-Ping; Liang, Jium-Jia; Tsai, Tong-Rong; Chou, Yu-Wei; Kuo, Kung-Kai; Chen, Chung-Yu; Wang, Jeh-Jeng [Journal of Medicinal Chemistry, 2013, vol. 56, # 13, p. 5422 - 5435]
[9]Nguefack, Jean-Flaubert; Bolitt, Veronique; Sinou, Denis [Tetrahedron Letters, 1996, vol. 37, # 31, p. 5527 - 5530]
[10]Dong, Yuping; Lam, Jacky W.Y.; Peng, Han; Cheuk, Kevin K.L.; Kwok, Hoi Sing; Tang, Ben Zhong [Macromolecules, 2004, vol. 37, # 17, p. 6408 - 6417]
[11]Bajracharya, Gan B.; Huo, Zhibao; Yamamoto, Yoshinori [Journal of Organic Chemistry, 2005, vol. 70, # 12, p. 4883 - 4886]
[12]Rizk, Toni; Bilodeau, Eric J.-F.; Beauchemin, Andre M. [Angewandte Chemie - International Edition, 2009, vol. 48, # 44, p. 8325 - 8327]
[13]Costello, Jeff P.; Ferreira, Eric M. [Organic Letters, 2019, vol. 21, # 24, p. 9934 - 9939]
[14]Lin, Guan-You; Yang, Chun-Yao; Liu, Rai-Shung [Journal of Organic Chemistry, 2007, vol. 72, # 18, p. 6753 - 6757]
[15]Koerner, Cindy; Starkov, Pavel; Sheppard, Tom D. [Journal of the American Chemical Society, 2010, vol. 132, # 17, p. 5968 - 5969]
[16]Börjesson, Marino; Moragas, Toni; Martin, Ruben [Journal of the American Chemical Society, 2016, vol. 138, # 24, p. 7504 - 7507]
[17]Liu, Shasha; Zhao, Jinbo; Kaminsky, Lauren; Wilson, Robert J.; Marino, Nadia; Clark, Daniel A. [Organic Letters, 2014, vol. 16, # 17, p. 4456 - 4459]
[18]Molinaro, Carmela; Jamison, Timothy F. [Journal of the American Chemical Society, 2003, vol. 125, # 27, p. 8076 - 8077]
[19]Atobe, Shingo; Sonoda, Motohiro; Suzuki, Yuki; Shinohara, Hiroyuki; Yamamoto, Takuya; Ogawa, Akiya [Chemistry Letters, 2011, vol. 40, # 9, p. 925 - 927]
[20]Stubbert, Bryan D.; Marks, Tobin J. [Journal of the American Chemical Society, 2007, vol. 129, # 14, p. 4253 - 4271]
[21]Wessig, Pablo; Mueller, Gunnar; Pick, Charlotte; Matthes, Annika [Synthesis, 2007, # 3, p. 464 - 477]
[22]Location in patent: scheme or table Page, Lee W.; Bailey, Matthew; Beswick, Paul J.; Frydrych, Simon; Gleave, Robert J. [Tetrahedron Letters, 2010, vol. 51, # 26, p. 3388 - 3391]
[23]Petrignet, Julien; Boudhar, Aicha; Blond, Gaelle; Suffert, Jean [Angewandte Chemie - International Edition, 2011, vol. 50, # 14, p. 3285 - 3289]
[24]Zhdanko, Alexander; Maier, Martin E. [Chemistry - A European Journal, 2014, vol. 20, # 7, p. 1918 - 1930]
[25]Zhou, Bing; Yang, Yaxi; Tang, Huanyu; Du, Juanjuan; Feng, Huijin; Li, Yuanchao [Organic Letters, 2014, vol. 16, # 15, p. 3900 - 3903]
[26]Cabrera-Lobera, Natalia; Quirós, M. Teresa; Buñuel, Elena; Cárdenas, Diego J. [Chemistry - A European Journal, 2019, vol. 25, # 64, p. 14512 - 14516]
[27]Zhang, Bo-Sheng; Wang, Fan; Gou, Xue-Ya; Yang, Ying-Hui; Jia, Wan-Yuan; Liang, Yong-Min; Wang, Xi-Cun; Li, Yuke; Quan, Zheng-Jun [Organic Letters, 2021, vol. 23, # 19, p. 7518 - 7523]

9
[ 928-90-5 ]
[ 63349-52-0 ]
[ 189131-92-8 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1422 - 1438

10
[ 764-60-3 ]
[ 928-90-5 ]

Yield	Reaction Conditions	Operation in experiment
84%	With potassium <i>tert</i>-butylate; lithium; Trimethylenediamine for 3h; Inert atmosphere;
52%	With sodium hydride; ethylenediamine In mineral oil at 0 - 70℃;
	With sodium amide In various solvent(s)

With potassium <i>tert</i>-butylate; lithium; Trimethylenediamine at 20℃; Inert atmosphere;

Reference： [1]Eskandari, Roozbeh; Hess, Jeremy P.; Tochtrop, Gregory P. [Chemical Communications, 2021, vol. 57, # 58, p. 7136 - 7139]
[2]Steib, Philip; Breit, Bernhard [Angewandte Chemie - International Edition, 2018, vol. 57, # 22, p. 6572 - 6576][Angew. Chem., 2018, vol. 130, p. 6682 - 6686,5]
[3]Durand, Sandrine; Parrain, Jean-Luc; Santelli, Maurice [Synthesis, 1998, # 7, p. 1015 - 1018]
[4]Xue, Yi; Zimmt, Matthew B. [Chemical Communications, 2011, vol. 47, # 31, p. 8832 - 8834]

11
[ 928-90-5 ]
[ 18303-04-3 ]
[ 309947-66-8 ]

Yield	Reaction Conditions	Operation in experiment
93%	With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; Inert atmosphere;
93%	With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃;
92%	With di-isopropyl azodicarboxylate; triphenylphosphine In benzene at 20℃; for 40h; Inert atmosphere;

	With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 3h; Inert atmosphere;
	Stage #1: 5-hexyl-1-ol With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at -15℃; for 0.25h; Stage #2: N-[(tert-butoxy)carbonyl]-4-methylbenzenesulfonamide In tetrahydrofuran at -15 - 20℃;

Reference： [1]Campbell, Craig D.; Greenaway, Rebecca L.; Holton, Oliver T.; Chapman, Helen A.; Anderson, Edward A. [Chemical Communications, 2014, vol. 50, # 40, p. 5187 - 5189]
[2]Campbell, Craig D.; Greenaway, Rebecca L.; Holton, Oliver T.; Walker, P. Ross; Chapman, Helen A.; Russell, C. Adam; Carr, Greg; Thomson, Amber L.; Anderson, Edward A. [Chemistry - A European Journal, 2015, vol. 21, # 36, p. 12627 - 12639]
[3]Borrero, Nicholas V.; Deratt, Lindsey G.; Ferreira Barbosa, Lais; Abboud, Khalil A.; Aponick, Aaron [Organic Letters, 2015, vol. 17, # 7, p. 1754 - 1757]
[4]Rainier, Jon D.; Imbriglio, Jason E. [Journal of Organic Chemistry, 2000, vol. 65, # 22, p. 7272 - 7276]
[5]Wang, Hong-Fa; Wang, Shi-Yue; Qin, Tian-Zhu; Zi, Weiwei [Chemistry - A European Journal, 2018, vol. 24, # 68, p. 17911 - 17914]
[6]Yang, Chun-Hua; Han, Meng; Li, Wenyan; Zhu, Ningning; Sun, Zhenzhen; Wang, Junjie; Yang, Zhantao; Li, Yue-Ming [Organic Letters, 2020, vol. 22, # 13, p. 5090 - 5093]

12
[ 98437-24-2 ]
[ 928-90-5 ]
5-benzofuran-2-yl-hex-5-en-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With acetic acid In 1,4-dioxane at 70℃; for 12h;

Reference： [1]Oh, Chang Ho; Jung, Hyung Hoon; Kim, Ki Seong; Kim, Nakjoong [Angewandte Chemie - International Edition, 2003, vol. 42, # 7, p. 805 - 808]

13
[ 928-90-5 ]
[ 154230-29-2 ]
(E)-7-(4-Chloro-phenyl)-5-methylene-hept-6-en-1-ol [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2003,vol. 42,p. 805 - 808

14
[ 557-93-7 ]
[ 928-90-5 ]
[ 732284-07-0 ]

Yield	Reaction Conditions	Operation in experiment
83%	With copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; for 17h;
67%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 50℃; for 12h; Inert atmosphere; Schlenk technique;
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine In tetrahydrofuran at 20℃; for 2h;

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine In tetrahydrofuran at 20℃; for 2h;

Reference： [1]Stephen; Hashmi; Sinha, Pradipta [Advanced Synthesis and Catalysis, 2004, vol. 346, # 4, p. 432 - 438]
[2]Xu, Ting; Wu, Shuang; Zhang, Quan-Na; Wu, You; Hu, Ming; Li, Jin-Heng [Organic Letters, 2021, vol. 23, # 21, p. 8455 - 8459]
[3]Blanc, Aurelien; Tenbrink, Katharina; Weibel, Jean-Marc; Pale, Patrick [Journal of Organic Chemistry, 2009, vol. 74, # 11, p. 4360 - 4363]
[4]Blanc, Aurelien; Tenbrink, Katharina; Weibel, Jean-Marc; Pale, Patrick [Journal of Organic Chemistry, 2009, vol. 74, # 15, p. 5342 - 5348]

15
[ 928-90-5 ]
[ 128143-88-4 ]
4'-hex-5-ynyloxy-[2,2';6',2'']terpyridine [ No CAS ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 5707 - 5709

16
[ 928-90-5 ]
[ 19978-41-7 ]
[ 748800-71-7 ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 5857 - 5860

17
[ 928-90-5 ]
[ 624-38-4 ]
[ 226955-86-8 ]

Yield	Reaction Conditions	Operation in experiment
94%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In dichloromethane at 20℃; for 12h; Inert atmosphere;	6,6'-(1,4-Phenylene)bis(hex-5-yn-1-ol) (S1a, S2a). An oven-dried 100 ml round-bottomed flask was charged with 1,4-diiodobenzene (S1, S2) (1.000 g, 3.03 mmol), PdCl2[P(C6H5)3]2 (106.4 mg, 0.15 mmol, 5.0 mol%), CuI (28.9 mg, 0.15 mmol, 5 mol%) under argon atmosphere, 5-hexyn-1-ol (0.85 mL, 7.58 mmol) was injected, then CH2Cl2/Et3N (30 ml/5 ml) was added. The resultant solution was stirred at room temperature for 12 hours. 1M hydrochloric acid solution was added and mixture extracted with dichloromethane. The combined organic layer was washed with water and dried over MgSO4. Solvent was removed by rotary evaporator after filtration. The residue was purified by column chromatography using a mixture of ethyl acetate/hexane (2/1) and furnished the product 6,6'-(1,4-phenylene)bis(hex-5-yn-1-ol) (S2a) (1.903 g, 94%) as white solids. 1H NMR (400 MHz, CDCl3): δ = 1.31 (brs, 2H), 1.67-1.76 (m, 8H), 2.46 (t, J = 6.3 Hz, 4H), 3.72 (t, J = 6.3 Hz, 4H), 7.29 (s, 4H). ; 13C NMR (125 MHz, CDCl3) δ = 19.3 (2C), 25.0 (2C), 31.9 (2C), 62.5 (2C), 80.7 (2C), 91.4 (2C), 123.1 (2C), 131.3 (4C); MS (EI): m/z (%): 270 (61) [M +], 129 (100); high-resolution MS (EI, 70 eV): calc. for C18H22O2: 270.1620, found: 270.1615.
88%	With copper(l) iodide; triethylamine In dichloromethane at 50℃;
	With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine In dichloromethane at 50℃;

Reference： [1]Lee, Kyu Hwan; Jillella, Raveendra; Kim, Jaewoong; Oh, Chang Ho [Bulletin of the Korean Chemical Society, 2018, vol. 39, # 5, p. 651 - 656]
[2]Ueda, Tsuyoshi; Kanomata, Nobuhiro; Machida, Hajime [Organic Letters, 2005, vol. 7, # 12, p. 2365 - 2368]
[3]Obando, Daniel; Koda, Yasuko; Pantarat, Namfon; Lev, Sophie; Zuo, Xiaoming; Bijosono Oei, Johanes; Widmer, Fred; Djordjevic, Julianne T.; Sorrell, Tania C.; Jolliffe, Katrina A. [ChemMedChem, 2018, vol. 13, # 14, p. 1421 - 1436]

18
[ 928-90-5 ]
[ 33775-94-9 ]
[ 924634-03-7 ]

Yield	Reaction Conditions	Operation in experiment
96%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine at 40℃; for 1.5h; Inert atmosphere;
	With copper(l) iodide; N-butylamine In diethyl ether at 20℃; for 4h;

Reference： [1]Balova, Irina A.; Danilkina, Natalia A.; Govdi, Anastasia I.; Khlebnikov, Alexander F.; Ryazantsev, Mikhail N.; Sharoyko, Vladimir V.; Shtyrov, Andrey A.; Tikhomirov, Alexander O.; Bräse, Stefan [Journal of the American Chemical Society, 2021, vol. 143, # 40, p. 16519 - 16537]
[2]Lu, Wen-Der; Wu, Ming-Jung [Tetrahedron, 2007, vol. 63, # 2, p. 356 - 362]

19
[ 928-90-5 ]
[ 40642-42-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 3 h / -10 - 20 °C 1.2: 62 percent / tetrahydrofuran; hexamethylphosphoric acid triamide 2.1: 95 percent / H₂; Lindlar catalyst; quinoline / pentane / 0.17 h / 0 °C / 3750.3 Torr

Reference： [1]Verniest, Guido; Boterberg, Stefaan; Colpaert, Jeroen; Van Thienen, Tinneke; Stevens, Christian V.; De Kimpe, Norbert [Synlett, 2004, # 7, p. 1273 - 1275]

20
[ 928-90-5 ]
[ 18202-10-3 ]

Reference： [1]Journal of the American Chemical Society,1987,vol. 109,p. 2138

21
[ 928-90-5 ]
[ 17924-92-4 ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 2883 - 2894

22
[ 928-90-5 ]
[ 354-38-1 ]
[ 124-63-0 ]
[ 149798-22-1 ]

Yield	Reaction Conditions	Operation in experiment
	With NaH;triethylamine;	N-trifluoroacetyl-1-amino-5-hexyne 5-Hexyn-1-ol was treated with methanesulfonyl chloride in the presence of triethylamine and an organic solvent to provide the corresponding methanesulfonate ester. Displacement of the ester with the sodium salt of <strong>[354-38-1]trifluoroacetamide</strong> (formed from NaH and <strong>[354-38-1]trifluoroacetamide</strong>) provides N-trifluoroacetyl-1-amino-5-hexyne.

Reference： [1]Patent: US5596091,1997,A

23
[ 928-90-5 ]
[ 27329-74-4 ]
[ 22206-57-1 ]
[ 106-93-4 ]
[ 113101-57-8 ]

Yield	Reaction Conditions	Operation in experiment
5.38 g (30%)	With magnesium; pyridinium chlorochromate; In tetrahydrofuran;	Example 10 Synthesis of 4-(1'-hydroxy-5'-hexynyl)-2,6-di-tert-butylphenol A mixture of 3.0 g (120 mmol) of magnesium, 25.7 g (72.0 mmol) of 2,6-di- t -butyl-4-bromo-1-trimethylsiloxybenzene and a few drops of 1,2-dibromoethane in 350 mL THF is heated at reflux for two hours and then is cooled to -78° and to it is added 5.78 g (60.0 mmol) of 5-hexynal (which is prepared from the oxidation of 5-hexyn-1-ol using pyridinium chlorochromate). The reaction mixture is stirred at -78° for 15 minutes and then is allowed to warm to 0°, where it is stirred for an additional 30 minutes. The mixture is poured into sat. NH4Cl and the aqueous layer is extracted with pentane. The combined organic phase is washed with sat. NaCl and dried (MgSO4). The crude silylated intermediate is concentrated, dissolved in 300 mL of THF, and treated at room temperature with 28.5 g (90.0 mmol) of tetra- n -butyl-ammonium fluoride trihydrate. After stirring the mixture at 25° for one hour, it is poured into sat. NH4Cl and the layers are separated. The aqueous portion is extracted with pentane and the combined organic phase is washed with sat. NaCl and then dried (MgSO4). The concentrate is purified by flash chromatography (10percent EtOAc/hexane, Rf=0.16) and recrystallization (hexane) to afford 5.38 g (30percent) of the title compound: mp 70-71°; IR (CCl4) 3620(s), 3310(m), 2960(s), 1430(s), 1160(s), 630(m) cmmin1; 1H-NMR (CDCl3)delta(ppm) 1.40(s, 18H), 1.5-2.3(m, 8H), 4.50(t, 1H), 5.15(s, 1H), 7.10(s, 2H); 13C-NMRdelta18.09, 24.88, 30.19, 34.22, 37.69, 68.51, 74.37, 84.25, 122.46, 135.16, 135.75, 153.04 ppm.
5.38 g (30%)	With magnesium; pyridinium chlorochromate; In tetrahydrofuran;	EXAMPLE 10 Synthesis of 4-(1'-hydroxy-5'-hexynyl)-2,6-di-tert-butylphenol STR24 A mixture of 3.0 g (120 mmol) of magnesium, 25.7 g (72.0 mmol) of 2,6-di-t-butyl-4-bromo-1-trimethylsiloxybenzene and a few drops of 1,2-dibromoethane in 350 mL THF is heated at reflux for two hours and then is cooled to -78° and to it is added 5.78 g (60.0 mmol) of 5-hexynal (which is prepared from the oxidation of 5-hexyn-1-ol using pyridinium chlorochromate). The reaction mixture is stirred at -78° for 15 minutes and then is allowed to warm to 0°, where it is stirred for an additional 30 minutes. The mixture is poured into sat. NH4 Cl and the aqueous layer is extracted with pentane. The combined organic phase is washed with sat. NaCl and dried (MgSO4). The crude silylated intermediate is concentrated, dissolved in 300 mL of THF, and treated at room temperature with 28.5 g (90.0 mmol) of <strong>[22206-57-1]tetra-n-butylammonium fluoride trihydrate</strong>. After stirring the mixture at 25° for one hour, it is poured into sat. NH4 Cl and the layers are separated. The aqueous portion is extracted with pentane and the combined organic phase is washed with sat. NaCl and then dried (MgSO4). The concentrate is purified by flash chromatography (10percent EtOAc/hexane, Rf =0.16) and recrystallization (hexane) to afford 5.38 g (30percent) of the title compound: mp 70°-71°; IR (CCl4) 3620(s), 3310(m), 2960(s), 1430(s), 1160(s), 630(m) cm-1; 1 H-NMR (CDCl3)delta(ppm) 1.40(s, 18H), 1.5-2.3(m, 8H), 4.50(t, 1H), 5.15(s, 1H), 7.10(s, 2H); 13 C-NMRdelta18.09, 24.88, 30.19, 34.22, 37.69, 68.51, 74.37, 84.25, 122.46, 135.16, 135.75, 153.04 ppm.

Reference： [1]Patent: EP251408,1991,B1
[2]Patent: US4708966,1987,A

24
[ 928-90-5 ]
[ 17955-46-3 ]
[ 489470-67-9 ]

Reference： [1]Chemical Communications,2002,p. 1884 - 1885
[2]Journal of Molecular Catalysis A: Chemical,2004,vol. 214,p. 33 - 44
[3]Chemical Communications,2002,p. 1884 - 1885
[4]Journal of Molecular Catalysis A: Chemical,2004,vol. 214,p. 33 - 44
[5]Journal of Molecular Catalysis A: Chemical,2004,vol. 214,p. 33 - 44

25
[Ru(hydrido trispyrazolylborate)(η4-cycloocta-1,5-diene)Cl] [ No CAS ]
[ 928-90-5 ]
[ 6372-40-3 ]
[Ru(HB(C₃H₃N₂)3)(P(C₆H₅)2CH(CH₃)2)(CO(CH₂)5)Cl] [ No CAS ]

Reference： [1]Journal of Organometallic Chemistry,2005,vol. 690,p. 5497 - 5507

26
[ 928-90-5 ]
[ 502649-73-2 ]
[ 1191447-01-4 ]

Reference： [1]Canadian Journal of Chemistry,2009,vol. 87,p. 1180 - 1199

27
[ 23784-96-5 ]
[ 928-90-5 ]
[ 1235527-78-2 ]

Reference： [1]Advanced Synthesis and Catalysis,2010,vol. 352,p. 1179 - 1192

28
[ 928-90-5 ]
[ 63-42-3 ]
[ 1190202-82-4 ]

Reference： [1]Tetrahedron,2010,vol. 66,p. 750 - 757

29
[ 50-00-0 ]
[ 928-90-5 ]
[ 102503-23-1 ]
7-((4-methoxybenzyl)(methyl)amino)hept-5-yn-1-ol [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 684 - 687

30
[ 928-90-5 ]
[ 164470-64-8 ]
[ 1221412-52-7 ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 1221 - 1223

31
[ 928-90-5 ]
[ 98-59-9 ]
[ 167316-27-0 ]
[ 78-79-5 ]
[ 1333982-28-7 ]
[ 1404469-11-9 ]

Yield	Reaction Conditions	Operation in experiment
		The tosylates (10.45 g, 32.61 mmol, isomer ratio: 1,4 type/1,5 type=77/23) obtained in Example 2 were dissolved in 40 ml of toluene, and DIPEA (4.79 g, 32.61 mmol) and (S,S)-TsDPEN (11.95 g, 32.61 mmol) were added thereto, followed by stirring at 135 C. for 14 hours. After that, the solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1). Thus, 9.31 g of the title compounds were obtained as a yellow oily substance. Yield: 55.5% (isomer ratio: 1,4 type/1,5 type=77/23). Note that the following NMR spectrum data are those of the mixture of the two isomers. [0063] 1H NMR (CDCl3, 300 MHz): delta 7.38-7.36 (m, 2H+2H?), 7.14-7.12 (m, 3H+3H?), 7.05-7.00 (m, 5H+5H?), 6.96-6.88 (m, 4H+4H?), 6.30 (brs, 1H+1H?), 5.60-5.58 (m, 1H?), 5.53-5.51 (m, 1H?), 5.41-5.40 (m, 1H), 5.37-5.36 (m, 1H), 4.24-4.22 (m, 1H+1H?), 3.60-3.58 (m, 1H+1H?), 2.55 (brs, 4H), 2.46-2.37 (m, 1H+1H?), 2.34 (s, 3H+3H?), 2.32-2.23 (m, 1H+1H?), 2.01 (brs, 4H?), 2.01-1.88 (m, 2H+2H?), 1.77 (s, 3H?), 1.67 (s, 3H), 1.46-1.28 (m, 5H+5H?); [0064] HRMS (ESI): calcd for C32H39N2O2S[M+H]+515.2727, found 515.2747
		In 45 mL of THF, 1,2-bis(diphenylphosphino) ethane (0.77 g, 1.93 mmol), cobalt bromide 0.41 (0.41 g, 1.87 mmol), zinc iodide (1.19 g, 3.73 mmol), and zinc (0.24 g, 3.67 mmol) were dissolved, followed by stirring at 70 C. for 15 minutes. After cooling to room temperature, isoprene (7.55 g, 110.83 mmol) was added. Then, 5-hexyn-1-ol (8.94 g, 91.09 mmol) was slowly added dropwise with cooling in a water bath. After stirring at 35 C. for 1 hour, the solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1). Thus, 13.34 g of the title compounds, alcohols, were obtained as a colorless oily substance. Yield: 88.10 (isomer ratio: 1,4 type/1,5 type=77/23). Note that the following NMR spectrum data are those of the isomer mixture; 1H-NMR (CDCl3, 300 MHz): delta 5.61-5.57 (m, 2H?), 5.43-5.41 (m, 2H), 3.67-3.63 (m, 2H+2H?), 2.58 (brs, 4H), 2.10 (brs, 4H?), 2.08 (t, J=6.9 Hz, 2H?), 2.00 (t, J=7.2 Hz, 2H), 1.76 (s, 3H?), 1.67 (s, 3H), 1.61-1.43 (m, 5H+5H); HRMS (ESI): calcd for C11H19O [M+H]+ 167.1430. found 167.1432 ; The alcohols (12.19 g, 73.32 mmol, isomer ratio: 1,4 type/1,5 type=77/23) obtained in Example 1, triethylamine (8.90 g, 87.98 mmol), and 1-methylimidazole (7.22 g, 87.98 mmol) were dissolved in 10 mL of toluene. With cooling in an ice-bath, a toluene solution (40 ml) of p-toluenesulfonyl chloride (15.94 g, 83.58 mmol) was slowly added dropwise, followed by stirring at room temperature for 1 hour. Tap water was added thereto, and the resultant layers were separated from each other. The obtained organic layer was washed with 2 M hydrochloric acid and tap water. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/1?4/1). Thus, 20.25 g of the title compounds, tosylates, were obtained as a colorless oily substance. Yield: 86.2% (isomer ratio: 1,4 type/1,5 type=77/23). Note that the following NMR spectrum data are those of the isomer mixture; 1H-NMR (CDCl3, 300 MHz): delta 7.80-7.77 (m, 2H+2H?), 7.36-7.33 (m, 2H+2H?), 5.58-5.56 (m, 1H?), 5.51-5.49 (m, 1H?), 5.39-5.38 (m, 1H), 5.35-5.34 (m, 1H), 4.05-4.01 (m, 2H+2H?), 2.53 (brs, 4H), 2.45 (s, 3H+3H?), 2.05 (brs, 4H?), 1.99 (t, J=7.4 Hz, 2H?), 1.91 (t, J=7.4 Hz, 2H), 1.76 (s, 3H?), 1.66 (s, 3H), 1.67-1.58 (m, 2H+2H?), 1.49-1.37 (m, 2H+2H?); HRMS (ESI): calcd for C18H24O3SNa [M+Na]+ 343.1338. found 343.1330; The tosylates (10.45 g, 32.61 mmol, isomer ratio: 1,4 type/1,5 type=77/23) obtained in Example 2 were dissolved in 40 ml of toluene, and DIPEA (4.79 g, 32.61 mmol) and (S,S)-TsDPEN (11.95 g, 32.61 mmol) were added thereto, followed by stirring at 135 C. for 14 hours. After that, the solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1). Thus, 9.31 g of the title compounds were obtained as a yellow oily substance. Yield: 55.5% (isomer ratio: 1,4 type/1,5 type=77/23). Note that the following NMR spectrum data are those of the isomer mixture.; 1H NMR (CDCl3, 300 MHz): delta 7.38-7.36 (m, 2H+2H?), 7.14-7.12 (m, 3H+3H?), 7.05-7.00 (m, 5H+5H?), 6.96-6.88 (m, 4H+4H?), 6.30 (brs, 1H+1H?), 5.60-5.58 (m, 1H?), 5.53-5.51 (m, 1H?), 5.41-5.40 (m, 1H), 5.37-5.36 (m, 1H), 4.24-4.22 (m, 1H+1H?), 3.60-3.58 (m, 1H+1H?), 2.55 (brs, 4H), 2.46-2.37 (m, 1H+1H?), 2.34 (s, 3H+3H?), 2.32-2.23 (m, 1H+1H?), 2.01 (brs, 4H?), 2.01-1.88 (m, 2H+2H?), 1.77 (s, 3H?), 1.67 (s, 3H), 1.46-1.28 (m, 5H+5H?); HRMS (ESI): calcd for C32H39N2O2S [M+H]+ 515.2727. found 515.2747

Reference： [1]Journal of the American Chemical Society,2011,vol. 133,p. 14960 - 14963
[2]Patent: US2014/39220,2014,A1 .Location in patent: Paragraph 0054-0064
[3]Patent: US2014/51871,2014,A1 .Location in patent: Paragraph 0067-0078

32
[ 928-90-5 ]
[ 5446-05-9 ]
[ 1344728-27-3 ]

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 7327 - 7334

33
[ 928-90-5 ]
[ 5326-39-6 ]
[ 1344728-25-1 ]

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 7327 - 7334

34
[ 928-90-5 ]
[ 89976-27-2 ]
[ 1344728-31-9 ]

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 7327 - 7334

35
[ 2777-65-3 ]
[ 928-90-5 ]
[ 1346556-99-7 ]

Yield	Reaction Conditions	Operation in experiment
99%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 15h; Inert atmosphere;
99%	With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 15h; Inert atmosphere;

Reference： [1]Bedard, Anne-Catherine; Collins, Shawn K. [Journal of the American Chemical Society, 2011, vol. 133, # 49, p. 19976 - 19981]
[2]Bedard, Anne-Catherine; Collins, Shawn K. [ACS Catalysis, 2013, vol. 3, # 4, p. 773 - 782]

36
[ 928-90-5 ]
[ 406-93-9 ]
[ 1338068-14-6 ]

Reference： [1]ACS Chemical Biology,2011,vol. 6,p. 1175 - 1181

37
[ 928-90-5 ]
[ 513-81-5 ]
[ 1360897-71-7 ]

Yield	Reaction Conditions	Operation in experiment
63.4%	With zinc(II) iodide; zinc In tetrahydrofuran at 20 - 35℃; for 1h; Inert atmosphere;	48 Production of 4-(4,5-dimethylcyclohexa- 1 ,4-dienyl)butan- 1 -ol[Chem. 32]800 mg (2.00 mmol) of l,2-bis(diphenylphosphino)ethane, 437 mg (2.00 mmol) of cobalt bromide, 1.28 g (4.00 mmol) of zinc iodide, and 260 mg (4.00 mmol) of zinc were added to 40 ml of THF, and the solution was stirred for 15 minutes at 70°C. The solution was cooled to room temperature, and 9.86 g (120 mmol) of 2,3-dimethyl-l,3-butadiene was added thereto. Subsequently, 9.8 g (100 mmol) of 5-hexyn-l-ol was slowly added dropwise to the mixture in a water bath. The resulting mixture was stirred for one hour at 35°C, and then the solvent was distilled off under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (hexane/ethyl acetate = 3/1), and thus 11.5 g of the title compound alcohol was obtained as a colorless oil. Yield 63.4%.1.28(bs, 1H), 1.79-1.46(m, 4H), 1.63(s, 6H), 1.98-2.11(m, 3H), 2.48-2.61(m, 2H), 3.63 -3.67(m, 2H), 5.41-5.56(m, 1H);
63.4%	With 1,2-bis-(diphenylphosphino)ethane; cobalt(II) bromide; zinc(II) iodide; zinc In tetrahydrofuran at 35℃; for 1h;	11 Production of 4-(4,5-dimethylcyclohexa-1,4-dienyl)butan-1-ol In 40 mL of THF, 1,2-bis(diphenylphosphino)ethane (800 mg, 2.00 mmol), cobalt bromide (437 mg, 2.00 mmol), zinc iodide (1.28 g, 4.00 mmol), and zinc (260 mg, 4.00 mmol) were dissolved, followed by stirring at 70° C. for 15 minutes. After cooling to room temperature, 2,3-dimethyl-1,3-butadiene (9.86 g, 120 mmol) was added. Then, 5-hexyn-1-ol (9.8 g, 100 mmol) was slowly added dropwise with cooling in a water bath. After stirring at 35° C. for 1 hour, the solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1). Thus, 11.5 g of the title compound, an alcohol, was obtained as a colorless oily substance. Yield: 63.4%. [0097] 1H NMR (CDCl3, 300 MHz): δ 5.56-5.41 (m, 1H), 3.67-3.63 (m, 2H), 2.61-2.48 (m, 2H), 2.11-1.98 (m, 3H), 1.63 (s, 6H), 1.79-1.46 (m, 4H), 1.28 (brs, 1H)
63.4%	With 1,2-bis-(diphenylphosphino)ethane; cobalt(II) bromide; zinc(II) iodide; zinc In tetrahydrofuran at 35℃; for 1h; Cooling;	11 Production of 4-(4,5-dimethylcyclohexa-1,4-dienyl)butan-1-ol Example 11 Production of 4-(4,5-dimethylcyclohexa-1,4-dienyl)butan-1-ol In 40 mL of THF, 1,2-bis(diphenylphosphino)ethane (800 mg, 2.00 mmol), cobalt bromide (437 mg, 2.00 mmol), zinc iodide (1.28 g, 4.00 mmol), and zinc (260 mg, 4.00 mmol) were dissolved, followed by stirring at 70° C. for 15 minutes. After cooling to room temperature, 2,3-dimethyl-1,3-butadiene (9.86 g, 120 mmol) was added. Then, 5-hexyn-1-ol (9.8 g, 100 mmol) was slowly added dropwise with cooling in a water bath. After stirring at 35° C. for 1 hour, the solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1). Thus, 11.5 g of the title compound, an alcohol, was obtained as a colorless oily substance. Yield: 63.4%. 1H NMR (CDCl3, 300 MHz): δ 5.56-5.41 (m, 1H), 3.67-3.63 (m, 2H), 2.61-2.48 (m, 2H), 2.11-1.98 (m, 3H), 1.63 (s, 6H), 1.79-1.46 (m, 4H), 1.28 (brs, 1H)

Reference： [1]Current Patent Assignee: TAKASAGO INTERNATIONAL CORPORATION - WO2012/26201, 2012, A1 Location in patent: Page/Page column 40
[2]Current Patent Assignee: TAKASAGO INTERNATIONAL CORPORATION - US2014/39220, 2014, A1 Location in patent: Paragraph 0096; 0097
[3]Current Patent Assignee: TAKASAGO INTERNATIONAL CORPORATION - US2014/51871, 2014, A1 Location in patent: Paragraph 0109 - 0111

38
[ 928-90-5 ]
[ 56413-96-8 ]
C₁₂H₁₁N₅O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In tetrahydrofuran at 80 - 85℃;

Reference： [1]Location in patent: scheme or table Ali, Hasrat; Van Lier, Johan E. [Tetrahedron Letters, 2012, vol. 53, # 36, p. 4824 - 4827]

39
[ 4720-86-9 ]
[ 928-90-5 ]
C₂₈H₃₄N₂O₄ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 11180 - 11183,4

40
[ 4720-86-9 ]
[ 928-90-5 ]
[ 1403759-90-9 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 11180 - 11183,4

41
[ 928-90-5 ]
[ 23530-40-7 ]
[ 1426308-75-9 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 1306 - 1309

42
[ 928-90-5 ]
[ 98-59-9 ]
[ 167316-27-0 ]
[ 78-79-5 ]
[ 1404469-13-1 ]
[ 1404469-15-3 ]

Yield	Reaction Conditions	Operation in experiment
		The amides (8.55 g, 16.61 mmol, isomer ratio: 1, 4 type/1, 5 type=77/23) obtained in Example 3 were dissolved in 33 ml of toluene. Under ice-cooling, a 1N HCl (methanolic solution) (3.46 g, 33.22 mmol) was added, followed by stirring at room temperature for 20 minutes. After that, the solvent was evaporated under reduced pressure. Thus, 8.85 g of the title compounds, diamine hydrochlorides, were obtained as a white solid. Yield: 96.7% (isomer ratio: 1,4 type/1,5 type=77/23). [0067] 1H-NMR (d6-DMSO, 300 MHz) delta: 9.61 (brs, 1H+1H?), 9.15 (brs, 1H+1H?), 8.85 (d, 1H+1H?), 7.29-6.79 (m, 14H+14H?), 5.55 (m, 1H?), 5.48 (m, 1H?), 5.36 (m, 1H), 5.31 (m, 1H), 4.82 (m, 1H+1H?), 4.54 (m, 1H+1H?), 2.66 (brs, 4H), 2.20 (s, 3H+3H?), 1.99 (brs, 4H?), 1.98-1.90 (m, 2H?), 1.90-1.82 (m, 2H), 1.71 (s, 3H?), 1.70-1.52 (m, 2H+2H?), 1.61 (s, 3H), 1.38-1.18 (m, 2H+2H?); [0068] HRMS (ESI): calcd for C32H39N2O2S [M-Cl]+515.2727, found 515.2728
		In 45 mL of THF, 1,2-bis(diphenylphosphino) ethane (0.77 g, 1.93 mmol), cobalt bromide 0.41 (0.41 g, 1.87 mmol), zinc iodide (1.19 g, 3.73 mmol), and zinc (0.24 g, 3.67 mmol) were dissolved, followed by stirring at 70 C. for 15 minutes. After cooling to room temperature, isoprene (7.55 g, 110.83 mmol) was added. Then, 5-hexyn-1-ol (8.94 g, 91.09 mmol) was slowly added dropwise with cooling in a water bath. After stirring at 35 C. for 1 hour, the solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1). Thus, 13.34 g of the title compounds, alcohols, were obtained as a colorless oily substance. Yield: 88.10 (isomer ratio: 1,4 type/1,5 type=77/23). Note that the following NMR spectrum data are those of the isomer mixture; 1H-NMR (CDCl3, 300 MHz): delta 5.61-5.57 (m, 2H?), 5.43-5.41 (m, 2H), 3.67-3.63 (m, 2H+2H?), 2.58 (brs, 4H), 2.10 (brs, 4H?), 2.08 (t, J=6.9 Hz, 2H?), 2.00 (t, J=7.2 Hz, 2H), 1.76 (s, 3H?), 1.67 (s, 3H), 1.61-1.43 (m, 5H+5H); HRMS (ESI): calcd for C11H19O [M+H]+ 167.1430. found 167.1432 ; The alcohols (12.19 g, 73.32 mmol, isomer ratio: 1,4 type/1,5 type=77/23) obtained in Example 1, triethylamine (8.90 g, 87.98 mmol), and 1-methylimidazole (7.22 g, 87.98 mmol) were dissolved in 10 mL of toluene. With cooling in an ice-bath, a toluene solution (40 ml) of p-toluenesulfonyl chloride (15.94 g, 83.58 mmol) was slowly added dropwise, followed by stirring at room temperature for 1 hour. Tap water was added thereto, and the resultant layers were separated from each other. The obtained organic layer was washed with 2 M hydrochloric acid and tap water. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/1?4/1). Thus, 20.25 g of the title compounds, tosylates, were obtained as a colorless oily substance. Yield: 86.2% (isomer ratio: 1,4 type/1,5 type=77/23). Note that the following NMR spectrum data are those of the isomer mixture; 1H-NMR (CDCl3, 300 MHz): delta 7.80-7.77 (m, 2H+2H?), 7.36-7.33 (m, 2H+2H?), 5.58-5.56 (m, 1H?), 5.51-5.49 (m, 1H?), 5.39-5.38 (m, 1H), 5.35-5.34 (m, 1H), 4.05-4.01 (m, 2H+2H?), 2.53 (brs, 4H), 2.45 (s, 3H+3H?), 2.05 (brs, 4H?), 1.99 (t, J=7.4 Hz, 2H?), 1.91 (t, J=7.4 Hz, 2H), 1.76 (s, 3H?), 1.66 (s, 3H), 1.67-1.58 (m, 2H+2H?), 1.49-1.37 (m, 2H+2H?); HRMS (ESI): calcd for C18H24O3SNa [M+Na]+ 343.1338. found 343.1330; The tosylates (10.45 g, 32.61 mmol, isomer ratio: 1,4 type/1,5 type=77/23) obtained in Example 2 were dissolved in 40 ml of toluene, and DIPEA (4.79 g, 32.61 mmol) and (S,S)-TsDPEN (11.95 g, 32.61 mmol) were added thereto, followed by stirring at 135 C. for 14 hours. After that, the solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1). Thus, 9.31 g of the title compounds were obtained as a yellow oily substance. Yield: 55.5% (isomer ratio: 1,4 type/1,5 type=77/23). Note that the following NMR spectrum data are those of the isomer mixture.; 1H NMR (CDCl3, 300 MHz): delta 7.38-7.36 (m, 2H+2H?), 7.14-7.12 (m, 3H+3H?), 7.05-7.00 (m, 5H+5H?), 6.96-6.88 (m, 4H+4H?), 6.30 (brs, 1H+1H?), 5.60-5.58 (m, 1H?), 5.53-5.51 (m, 1H?), 5.41-5.40 (m, 1H), 5.37-5.36 (m, 1H), 4.24-4.22 (m, 1H+1H?), 3.60-3.58 (m, 1H+1H?), 2.55 (brs, 4H), 2.46-2.37 (m, 1H+1H?), 2.34 (s, 3H+3H?), 2.32-2.23 (m, 1H+1H?), 2.01 (brs, 4H?), 2.01-1.88 (m, 2H+2H?), 1.77 (s, 3H?), 1.67 (s, 3H), 1.46-1.28 (m, 5H+5H?); HRMS (ESI): calcd for C32H39N2O2S [M+H]+ 515.2727. found 515.2747; The amides (8.55 g, 16.61 mmol, isomer ratio: 1,4 type/1,5 type=77/23) obtained in Example 3 were dissolved in 33 ml of toluene. Under ice-cooling, a 1 M hydrochloric acid methanolic solution (3.46 g, 33.22 mmol) was added, followed by stirring at room temperature for 20 minutes. After that, the solvent was evaporated under reduced pressure. Thus, 8.85 g of the title compounds, diamine hydrochlorides, were obtained as a white solid. Yield: 96.7% (isomer ratio: 1,4 type/1,5 type-77/23). Note that the following NMR spectrum data are those of the isomer mixture; 1H-NMR (d6-DMSO, 300 MHz) delta: 9.61 (brs, 1H+1H?), 9.15 (brs, 1H+1H?), 8.85 (d, 1H+1H?), 7.29-6.79 (m, 14H+14H?), 5.55 (m, 1H?), 5.48 (m, 1H?), 5.36 (m, 1H), 5.31 (m, 1H), 4.82 (m, 1H+1H?), 4.54 (m, 1H+1H?), 2.66 (brs, 4H), 2.20 (s, 3H+3H?), 1.99 (brs, 4H?), 1.98-1.90 (m, 2H?), 1.90-1.82 (m, 2H), 1.71 (s, 3H?), 1.70-1.52 (m, 2H+2H?), 1.61 (s, 3H), 1.38-1.18 (m, 2H+2H?); HRMS (ESI): calcd for C32H39N2O2S [M-Cl]+515.2727. found 515.2728

Reference： [1]Patent: US2014/39220,2014,A1 .Location in patent: Paragraph 0054-0068
[2]Patent: US2014/51871,2014,A1 .Location in patent: Paragraph 0067-0083

43
[ 928-90-5 ]
ruthenium(III) chloride trihydrate [ No CAS ]
[ 98-59-9 ]
[ 167316-27-0 ]
[ 78-79-5 ]
C₆₄H₇₂Cl₄N₄O₄Ru₂S₂*ClH [ No CAS ]
C₆₄H₇₂Cl₄N₄O₄Ru₂S₂*ClH [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		The hydrochlorides (7.42 g, 13.46 mmol, isomer ratio: 1,4 type/1,5 type=77/23) obtained in Example 4 and ruthenium trichloride.trihydrate (3.20 g, 12.25 mmol) were dissolved in a mixture solvent of 110 ml of 3-methoxypropanol and 37 ml of water, followed by stirring at 120 C. for 1 hour. The solvent was evaporated under reduced pressure, and diethyl ether was added to the obtained residue, followed by stirring at room temperature for 15 minutes. The precipitated crystals were filtered. Thus, 10.15 g of the title compounds, ruthenium dimers, were obtained. Yield: 52.3%. The following NMR spectrum data are those of the major product (1,4 type). [0071] 1H NMR (d6-DMSO, 500 MHz): delta 9.61 (brs, 2H), 9.11 (brs, 2H), 8.78 (d, J=9.1 Hz, 2H), 7.30-6.88 (m, 28H), 6.82-6.81 (m, 8H), 4.83 (m, 2H), 4.56 (m, 2H), 2.71 (brs, 4H), 2.35 (t, J=7.5 Hz, 4H), 2.22 (s, 6H), 2.10 (s, 6H), 1.80-1.60 (m, 4H), 1.60-1.42 (m, 4H); [0072] HRMS (FD): calcd for C32H35ClN2O2RuS [M/2-2HCl]+.648.1156, found 648.1182

Reference： [1]Patent: US2014/39220,2014,A1 .Location in patent: Paragraph 0054-0072

44
[ 928-90-5 ]
ruthenium(III) chloride trihydrate [ No CAS ]
[ 98-59-9 ]
[ 167316-27-0 ]
[ 78-79-5 ]
(S,S)-RuCl(η6-CH3C6H4CH2CH2CH2CH2NHCH(C6H5)CH(C6H5)NSO2Ts) [ No CAS ]
C₃₂H₃₅ClN₂O₂RuS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		The ruthenium dimers (9.12 g, 6.32 mmol) obtained in Example 5 were dissolved in 155 ml of 2-propanol, and triethylamine (2.53 g, 25.29 mmol) was added thereto, followed by stirring at 60 C. for 1 hour. After that, the solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel chromatography (chloroform/methanol=20/1). Thus, 6.77 g of the title compounds, ruthenium monomers, were obtained. Yield: 82.6% (the chemical purity based on HPLC was 97.2%). The following NMR spectrum data are those of the major product (1,4 type). [0075] 1H NMR (CD2Cl2, 500 MHz): delta 7.17 (d, J=7.9 Hz, 2H), 7.10-7.05 (m, 3H), 6.86 (d, J=7.9 Hz, 2H), 6.82-6.79 (m, 1H), 6.74 (d, J=6.4 Hz, 2H), 6.68 (dd, J=7.9 Hz, 2H), 6.56 (d, J=7.9 Hz, 2H), 6.18 (d, J=5.6 Hz, 1H), 5.55 (d, J=6.3 Hz, 1H), 5.35 (d, J=6.3 Hz, 1H), 5.29 (d, J=5.6 Hz, 1H), 4.73-4.70 (m, 1H), 3.97 (d, J=11.0 Hz, 1H), 3.81 (dd, J=11.0, 12.2 Hz, 1H), 3.52-3.47 (m, 1H), 3.13-3.07 (m, 1H), 2.85-2.81 (m, 1H), 2.75-2.69 (m, 1H), 2.44 (s, 3H), 2.26 (s, 3H), 2.28-2.17 (m, 1H), 2.15-2.04 (m, 1H), 1.96-1.88 (m, 1H), 1.67-1.60 (m, 1H); [0076] HRMS (ESI): calcd for C32H36ClN2O2RuS [M+H]+649.1224, found 649.1224

Reference： [1]Patent: US2014/39220,2014,A1 .Location in patent: Paragraph 0054-0076

45
[ 300345-76-0 ]
[ 928-90-5 ]
[ 98-59-9 ]
[ 9003-31-0 ]
[ 1404469-27-7 ]
[ 1404469-32-4 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 5-hexyl-1-ol; isoprene With 1,2-bis-(diphenylphosphino)ethane; cobalt(II) bromide; zinc(II) iodide; zinc In tetrahydrofuran at 35℃; for 1h; Stage #2: p-toluenesulfonyl chloride With 1-methyl-1H-imidazole; triethylamine In toluene at 20℃; for 1h; Cooling with ice; Stage #3: (1S,2S)-N-methanesulfonyl-1,2-diphenylethane-1,2-diamine With N-ethyl-N,N-diisopropylamine In toluene at 135℃; for 16h; Overall yield = 5.72 g;	7 Production of N-((1S,2S)-2-(4-(4-methylcyclohexa-1,4-dienyl)butylamino)-1,2-diphenylethyl)methanesulfonamide and N-((1S,2S)-2-(4-(5-methylcyclohexa-1,4-dienyl)butylamino)-1,2-diphenylethyl)methanesulfonamide The tosylates (5.11 g, 15.95 mmol) obtained in Example 2 were dissolved in 20 ml of toluene, and DIPEA (2.05 g, 15.95 mmol) and (S,S)-MsDPEN (4.63 g, 15.95 mmol) were added thereto, followed by stirring at 135° C. for 16 hours. After that, the solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1). Thus, 5.72 g of the title compounds, diamines, were obtained as a yellow oily substance. [0079] Yield: 81.8% (isomer ratio: 1,4 type/1,5 type=77/23). Note that the following NMR spectrum data are those of the mixture of the two isomers. [0080] 1H NMR (CDCl3, 300 MHz): δ 7.26-7.19 (m, 10H+10H′), 6.23 (brs, 1H+1H′), 5.59-5.58 (m, 1H′), 5.52-5.51 (m, 1H′), 5.40 (m, 1H), 5.36 (m, 1H), 4.47-4.44 (m, 1H+1H′), 3.75-3.72 (m, 1H+1H′), 2.55 (brs, 4H), 2.46-2.37 (m, 1H+1H′), 2.34 (s, 3H+3H′), 2.32-2.23 (m, 1H+1H′), 2.01 (brs, 4H′), 2.01-1.88 (m, 2H+2H′), 1.77 (s, 3H′), 1.67 (s, 3H), 1.46-1.28 (m, 5H+5H′); [0081] HRMS (ESI): calcd for C26H35N2O2S [M+H]+439.2414, found 439.2409
	Stage #1: 5-hexyl-1-ol; isoprene With 1,2-bis-(diphenylphosphino)ethane; cobalt(II) bromide; zinc(II) iodide; zinc In tetrahydrofuran at 20 - 35℃; for 1h; Stage #2: p-toluenesulfonyl chloride With 1-methyl-1H-imidazole; triethylamine In toluene at 20℃; for 1h; Cooling with ice; Stage #3: (1S,2S)-N-methanesulfonyl-1,2-diphenylethane-1,2-diamine With N-ethyl-N,N-diisopropylamine In toluene at 135℃; for 16h; Overall yield = 5.72 g;	7 Example 7; Production of N-((1S,2S)-2-(4-(4-methylcyclohexa-1,4-dienyl)butylamino)-1,2-diphenylethyl)methanesulfonamide and N-((1S,2S)-2-(4-(5-methylcyclohexa-1,4-dienyl)butylamino)-1,2-diphenylethyl)methanesulfonamide In 45 mL of THF, 1,2-bis(diphenylphosphino) ethane (0.77 g, 1.93 mmol), cobalt bromide 0.41 (0.41 g, 1.87 mmol), zinc iodide (1.19 g, 3.73 mmol), and zinc (0.24 g, 3.67 mmol) were dissolved, followed by stirring at 70° C. for 15 minutes. After cooling to room temperature, isoprene (7.55 g, 110.83 mmol) was added. Then, 5-hexyn-1-ol (8.94 g, 91.09 mmol) was slowly added dropwise with cooling in a water bath. After stirring at 35° C. for 1 hour, the solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1). Thus, 13.34 g of the title compounds, alcohols, were obtained as a colorless oily substance. Yield: 88.10 (isomer ratio: 1,4 type/1,5 type=77/23). Note that the following NMR spectrum data are those of the isomer mixture. 1H-NMR (CDCl3, 300 MHz): δ 5.61-5.57 (m, 2H′), 5.43-5.41 (m, 2H), 3.67-3.63 (m, 2H+2H′), 2.58 (brs, 4H), 2.10 (brs, 4H′), 2.08 (t, J=6.9 Hz, 2H′), 2.00 (t, J=7.2 Hz, 2H), 1.76 (s, 3H′), 1.67 (s, 3H), 1.61-1.43 (m, 5H+5H′); HRMS (ESI): calcd for C11H19O [M+H]+ 167.1430. found 167.1432 ; The alcohols (12.19 g, 73.32 mmol, isomer ratio: 1,4 type/1,5 type=77/23) obtained in Example 1, triethylamine (8.90 g, 87.98 mmol), and 1-methylimidazole (7.22 g, 87.98 mmol) were dissolved in 10 mL of toluene. With cooling in an ice-bath, a toluene solution (40 ml) of p-toluenesulfonyl chloride (15.94 g, 83.58 mmol) was slowly added dropwise, followed by stirring at room temperature for 1 hour. Tap water was added thereto, and the resultant layers were separated from each other. The obtained organic layer was washed with 2 M hydrochloric acid and tap water. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/1→4/1). Thus, 20.25 g of the title compounds, tosylates, were obtained as a colorless oily substance. Yield: 86.2% (isomer ratio: 1,4 type/1,5 type=77/23). Note that the following NMR spectrum data are those of the isomer mixture. 1H-NMR (CDCl3, 300 MHz): δ 7.80-7.77 (m, 2H+2H′), 7.36-7.33 (m, 2H+2H′), 5.58-5.56 (m, 1H′), 5.51-5.49 (m, 1H′), 5.39-5.38 (m, 1H), 5.35-5.34 (m, 1H), 4.05-4.01 (m, 2H+2H′), 2.53 (brs, 4H), 2.45 (s, 3H+3H′), 2.05 (brs, 4H′), 1.99 (t, J=7.4 Hz, 2H′), 1.91 (t, J=7.4 Hz, 2H), 1.76 (s, 3H′), 1.66 (s, 3H), 1.67-1.58 (m, 2H+2H′), 1.49-1.37 (m, 2H+2H′); HRMS (ESI): calcd for C18H24O3SNa [M+Na]+ 343.1338. found 343.1330; The tosylates (5.11 g, 15.95 mmol) obtained in Example 2 were dissolved in 20 ml of toluene, and DIPEA (2.05 g, 15.95 mmol) and (S,S)-MsDPEN (4.63 g, 15.95 mmol) were added thereto, followed by stirring at 135° C. for 16 hours. After that, the solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1). Thus, 5.72 g of the title compounds, diamines, were obtained as a yellow oily substance. Yield: 81.8% (isomer ratio: 1,4 type/1,5 type=77/23). Note that the following NMR spectrum data are those of the mixture of the two isomers. 1H NMR (CDCl3, 300 MHz): δ 7.26-7.19 (m, 10H+10H′), 6.23 (brs, 1H+1H′), 5.59-5.58 (m, 1H′), 5.52-5.51 (m, 1H′), 5.40 (m, 1H), 5.36 (m, 1H), 4.47-4.44 (m, 1H+1H′), 3.75-3.72 (m, 1H+1H′), 2.55 (brs, 4H), 2.46-2.37 (m, 1H+1H′), 2.34 (s, 3H+3H′), 2.32-2.23 (m, 1H+1H′), 2.01 (brs, 4H′), 2.01-1.88 (m, 2H+2H′), 1.77 (s, 3H′), 1.67 (s, 3H), 1.46-1.28 (m, 5H+5H′); [HRMS (ESI): calcd for C26H35N2O2S [M+H]+ 439.2414. found 439.2409

Reference： [1]Current Patent Assignee: TAKASAGO INTERNATIONAL CORPORATION - US2014/39220, 2014, A1 Location in patent: Paragraph 0054-0056; 0078-0081
[2]Current Patent Assignee: TAKASAGO INTERNATIONAL CORPORATION - US2014/51871, 2014, A1 Location in patent: Paragraph 0092-0095

46
ruthenium trichloride trihydrate [ No CAS ]
[ 928-90-5 ]
[ 98-59-9 ]
[ 167316-27-0 ]
[ 78-79-5 ]
C₆₄H₇₂Cl₄N₄O₄Ru₂S₂*2ClH [ No CAS ]
C₆₄H₇₂Cl₄N₄O₄Ru₂S₂*2ClH [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		In 45 mL of THF, 1,2-bis(diphenylphosphino) ethane (0.77 g, 1.93 mmol), cobalt bromide 0.41 (0.41 g, 1.87 mmol), zinc iodide (1.19 g, 3.73 mmol), and zinc (0.24 g, 3.67 mmol) were dissolved, followed by stirring at 70 C. for 15 minutes. After cooling to room temperature, isoprene (7.55 g, 110.83 mmol) was added. Then, 5-hexyn-1-ol (8.94 g, 91.09 mmol) was slowly added dropwise with cooling in a water bath. After stirring at 35 C. for 1 hour, the solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1). Thus, 13.34 g of the title compounds, alcohols, were obtained as a colorless oily substance. Yield: 88.10 (isomer ratio: 1,4 type/1,5 type=77/23). Note that the following NMR spectrum data are those of the isomer mixture; 1H-NMR (CDCl3, 300 MHz): delta 5.61-5.57 (m, 2H?), 5.43-5.41 (m, 2H), 3.67-3.63 (m, 2H+2H?), 2.58 (brs, 4H), 2.10 (brs, 4H?), 2.08 (t, J=6.9 Hz, 2H?), 2.00 (t, J=7.2 Hz, 2H), 1.76 (s, 3H?), 1.67 (s, 3H), 1.61-1.43 (m, 5H+5H); HRMS (ESI): calcd for C11H19O [M+H]+ 167.1430. found 167.1432 ; The alcohols (12.19 g, 73.32 mmol, isomer ratio: 1,4 type/1,5 type=77/23) obtained in Example 1, triethylamine (8.90 g, 87.98 mmol), and 1-methylimidazole (7.22 g, 87.98 mmol) were dissolved in 10 mL of toluene. With cooling in an ice-bath, a toluene solution (40 ml) of p-toluenesulfonyl chloride (15.94 g, 83.58 mmol) was slowly added dropwise, followed by stirring at room temperature for 1 hour. Tap water was added thereto, and the resultant layers were separated from each other. The obtained organic layer was washed with 2 M hydrochloric acid and tap water. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/1?4/1). Thus, 20.25 g of the title compounds, tosylates, were obtained as a colorless oily substance. Yield: 86.2% (isomer ratio: 1,4 type/1,5 type=77/23). Note that the following NMR spectrum data are those of the isomer mixture; 1H-NMR (CDCl3, 300 MHz): delta 7.80-7.77 (m, 2H+2H?), 7.36-7.33 (m, 2H+2H?), 5.58-5.56 (m, 1H?), 5.51-5.49 (m, 1H?), 5.39-5.38 (m, 1H), 5.35-5.34 (m, 1H), 4.05-4.01 (m, 2H+2H?), 2.53 (brs, 4H), 2.45 (s, 3H+3H?), 2.05 (brs, 4H?), 1.99 (t, J=7.4 Hz, 2H?), 1.91 (t, J=7.4 Hz, 2H), 1.76 (s, 3H?), 1.66 (s, 3H), 1.67-1.58 (m, 2H+2H?), 1.49-1.37 (m, 2H+2H?); HRMS (ESI): calcd for C18H24O3SNa [M+Na]+ 343.1338. found 343.1330; The tosylates (10.45 g, 32.61 mmol, isomer ratio: 1,4 type/1,5 type=77/23) obtained in Example 2 were dissolved in 40 ml of toluene, and DIPEA (4.79 g, 32.61 mmol) and (S,S)-TsDPEN (11.95 g, 32.61 mmol) were added thereto, followed by stirring at 135 C. for 14 hours. After that, the solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1). Thus, 9.31 g of the title compounds were obtained as a yellow oily substance. Yield: 55.5% (isomer ratio: 1,4 type/1,5 type=77/23). Note that the following NMR spectrum data are those of the isomer mixture.; 1H NMR (CDCl3, 300 MHz): delta 7.38-7.36 (m, 2H+2H?), 7.14-7.12 (m, 3H+3H?), 7.05-7.00 (m, 5H+5H?), 6.96-6.88 (m, 4H+4H?), 6.30 (brs, 1H+1H?), 5.60-5.58 (m, 1H?), 5.53-5.51 (m, 1H?), 5.41-5.40 (m, 1H), 5.37-5.36 (m, 1H), 4.24-4.22 (m, 1H+1H?), 3.60-3.58 (m, 1H+1H?), 2.55 (brs, 4H), 2.46-2.37 (m, 1H+1H?), 2.34 (s, 3H+3H?), 2.32-2.23 (m, 1H+1H?), 2.01 (brs, 4H?), 2.01-1.88 (m, 2H+2H?), 1.77 (s, 3H?), 1.67 (s, 3H), 1.46-1.28 (m, 5H+5H?); HRMS (ESI): calcd for C32H39N2O2S [M+H]+ 515.2727. found 515.2747; The amides (8.55 g, 16.61 mmol, isomer ratio: 1,4 type/1,5 type=77/23) obtained in Example 3 were dissolved in 33 ml of toluene. Under ice-cooling, a 1 M hydrochloric acid methanolic solution (3.46 g, 33.22 mmol) was added, followed by stirring at room temperature for 20 minutes. After that, the solvent was evaporated under reduced pressure. Thus, 8.85 g of the title compounds, diamine hydrochlorides, were obtained as a white solid. Yield: 96.7% (isomer ratio: 1,4 type/1,5 type-77/23). Note that the following NMR spectrum data are those of the isomer mixture; 1H-NMR (d6-DMSO, 300 MHz) delta: 9.61 (brs, 1H+1H?), 9.15 (brs, 1H+1H?), 8.85 (d, 1H+1H?), 7.29-6.79 (m, 14H+14H?), 5.55 (m, 1H?), 5.48 (m, 1H?), 5.36 (m, 1H), 5.31 (m, 1H), 4.82 (m, 1H+1H?), 4.54 (m, 1H+1H?), 2.66 (brs, 4H), 2.20 (s, 3H+3H?), 1.99 (brs, 4H?), 1.98-1.90 (m, 2H?), 1.90-1.82 (m, 2H), 1.71 (s, 3H?), 1.70-1.52 (m, 2H+2H?), 1.61 (s, 3H), 1.38-1.18 (m, 2H+2H?); HRMS (ESI): calcd for C32H39N2O2S [M-Cl]+515.2727. found 515.2728; The hydrochlorides (7.42 g, 13.46 mmol, isomer ratio: 1,4 type/1,5 type=77/23) obtained in Example 4 and ruthenium trichloride.trihydrate (3.20 g, 12.25 mmol) were dissolved in a mixture solvent of 110 ml of 3-methoxypropanol and 37 ml of water, followed by stirring at 120 C. for 1 hour. The solvent was evaporated under reduced pressure, and diethyl ether was adde...

Reference： [1]Patent: US2014/51871,2014,A1 .Location in patent: Paragraph 0067-0087

47
ruthenium trichloride trihydrate [ No CAS ]
[ 928-90-5 ]
[ 98-59-9 ]
[ 167316-27-0 ]
[ 78-79-5 ]
(S,S)-RuCl(η6-CH3C6H4CH2CH2CH2CH2NHCH(C6H5)CH(C6H5)NSO2Ts) [ No CAS ]
C₃₂H₃₅ClN₂O₂RuS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		In 45 mL of THF, 1,2-bis(diphenylphosphino) ethane (0.77 g, 1.93 mmol), cobalt bromide 0.41 (0.41 g, 1.87 mmol), zinc iodide (1.19 g, 3.73 mmol), and zinc (0.24 g, 3.67 mmol) were dissolved, followed by stirring at 70 C. for 15 minutes. After cooling to room temperature, isoprene (7.55 g, 110.83 mmol) was added. Then, 5-hexyn-1-ol (8.94 g, 91.09 mmol) was slowly added dropwise with cooling in a water bath. After stirring at 35 C. for 1 hour, the solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=3/1). Thus, 13.34 g of the title compounds, alcohols, were obtained as a colorless oily substance. Yield: 88.10 (isomer ratio: 1,4 type/1,5 type=77/23). Note that the following NMR spectrum data are those of the isomer mixture; 1H-NMR (CDCl3, 300 MHz): delta 5.61-5.57 (m, 2H?), 5.43-5.41 (m, 2H), 3.67-3.63 (m, 2H+2H?), 2.58 (brs, 4H), 2.10 (brs, 4H?), 2.08 (t, J=6.9 Hz, 2H?), 2.00 (t, J=7.2 Hz, 2H), 1.76 (s, 3H?), 1.67 (s, 3H), 1.61-1.43 (m, 5H+5H); HRMS (ESI): calcd for C11H19O [M+H]+ 167.1430. found 167.1432 ; The alcohols (12.19 g, 73.32 mmol, isomer ratio: 1,4 type/1,5 type=77/23) obtained in Example 1, triethylamine (8.90 g, 87.98 mmol), and 1-methylimidazole (7.22 g, 87.98 mmol) were dissolved in 10 mL of toluene. With cooling in an ice-bath, a toluene solution (40 ml) of p-toluenesulfonyl chloride (15.94 g, 83.58 mmol) was slowly added dropwise, followed by stirring at room temperature for 1 hour. Tap water was added thereto, and the resultant layers were separated from each other. The obtained organic layer was washed with 2 M hydrochloric acid and tap water. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=20/1?4/1). Thus, 20.25 g of the title compounds, tosylates, were obtained as a colorless oily substance. Yield: 86.2% (isomer ratio: 1,4 type/1,5 type=77/23). Note that the following NMR spectrum data are those of the isomer mixture; 1H-NMR (CDCl3, 300 MHz): delta 7.80-7.77 (m, 2H+2H?), 7.36-7.33 (m, 2H+2H?), 5.58-5.56 (m, 1H?), 5.51-5.49 (m, 1H?), 5.39-5.38 (m, 1H), 5.35-5.34 (m, 1H), 4.05-4.01 (m, 2H+2H?), 2.53 (brs, 4H), 2.45 (s, 3H+3H?), 2.05 (brs, 4H?), 1.99 (t, J=7.4 Hz, 2H?), 1.91 (t, J=7.4 Hz, 2H), 1.76 (s, 3H?), 1.66 (s, 3H), 1.67-1.58 (m, 2H+2H?), 1.49-1.37 (m, 2H+2H?); HRMS (ESI): calcd for C18H24O3SNa [M+Na]+ 343.1338. found 343.1330; The tosylates (10.45 g, 32.61 mmol, isomer ratio: 1,4 type/1,5 type=77/23) obtained in Example 2 were dissolved in 40 ml of toluene, and DIPEA (4.79 g, 32.61 mmol) and (S,S)-TsDPEN (11.95 g, 32.61 mmol) were added thereto, followed by stirring at 135 C. for 14 hours. After that, the solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=2/1). Thus, 9.31 g of the title compounds were obtained as a yellow oily substance. Yield: 55.5% (isomer ratio: 1,4 type/1,5 type=77/23). Note that the following NMR spectrum data are those of the isomer mixture.; 1H NMR (CDCl3, 300 MHz): delta 7.38-7.36 (m, 2H+2H?), 7.14-7.12 (m, 3H+3H?), 7.05-7.00 (m, 5H+5H?), 6.96-6.88 (m, 4H+4H?), 6.30 (brs, 1H+1H?), 5.60-5.58 (m, 1H?), 5.53-5.51 (m, 1H?), 5.41-5.40 (m, 1H), 5.37-5.36 (m, 1H), 4.24-4.22 (m, 1H+1H?), 3.60-3.58 (m, 1H+1H?), 2.55 (brs, 4H), 2.46-2.37 (m, 1H+1H?), 2.34 (s, 3H+3H?), 2.32-2.23 (m, 1H+1H?), 2.01 (brs, 4H?), 2.01-1.88 (m, 2H+2H?), 1.77 (s, 3H?), 1.67 (s, 3H), 1.46-1.28 (m, 5H+5H?); HRMS (ESI): calcd for C32H39N2O2S [M+H]+ 515.2727. found 515.2747; The amides (8.55 g, 16.61 mmol, isomer ratio: 1,4 type/1,5 type=77/23) obtained in Example 3 were dissolved in 33 ml of toluene. Under ice-cooling, a 1 M hydrochloric acid methanolic solution (3.46 g, 33.22 mmol) was added, followed by stirring at room temperature for 20 minutes. After that, the solvent was evaporated under reduced pressure. Thus, 8.85 g of the title compounds, diamine hydrochlorides, were obtained as a white solid. Yield: 96.7% (isomer ratio: 1,4 type/1,5 type-77/23). Note that the following NMR spectrum data are those of the isomer mixture; 1H-NMR (d6-DMSO, 300 MHz) delta: 9.61 (brs, 1H+1H?), 9.15 (brs, 1H+1H?), 8.85 (d, 1H+1H?), 7.29-6.79 (m, 14H+14H?), 5.55 (m, 1H?), 5.48 (m, 1H?), 5.36 (m, 1H), 5.31 (m, 1H), 4.82 (m, 1H+1H?), 4.54 (m, 1H+1H?), 2.66 (brs, 4H), 2.20 (s, 3H+3H?), 1.99 (brs, 4H?), 1.98-1.90 (m, 2H?), 1.90-1.82 (m, 2H), 1.71 (s, 3H?), 1.70-1.52 (m, 2H+2H?), 1.61 (s, 3H), 1.38-1.18 (m, 2H+2H?); HRMS (ESI): calcd for C32H39N2O2S [M-Cl]+515.2727. found 515.2728; The hydrochlorides (7.42 g, 13.46 mmol, isomer ratio: 1,4 type/1,5 type=77/23) obtained in Example 4 and ruthenium trichloride.trihydrate (3.20 g, 12.25 mmol) were dissolved in a mixture solvent of 110 ml of 3-methoxypropanol and 37 ml of water, followed by stirring at 120 C. for 1 hour. The solvent was evaporated under reduced pressure, and diethyl ether was adde...

Reference： [1]Patent: US2014/51871,2014,A1 .Location in patent: Paragraph 0067-0091

48
[ 928-90-5 ]
[ 131222-99-6 ]
6,12-bis(6-hydroxyhex-1-yn-1-yl)chrysene [ No CAS ]

Reference： [1]Chemical Science,2014,vol. 5,p. 1506 - 1512

49
[ 274-87-3 ]
[ 928-90-5 ]
[ 1612226-50-2 ]

Reference： [1]Inorganic Chemistry,2014,vol. 53,p. 6204 - 6223

50
[ 89282-03-1 ]
[ 928-90-5 ]
2-(4-hydroxybutyl)furo[3,2-c]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With 5%-palladium/activated carbon; caesium carbonate; lithium chloride; In N,N-dimethyl-formamide; at 150℃; for 20.0h;	General procedure: In a pressure tube, a suspension of 5% Pd/C (5 mol%), 2-bromo-3-hydroxypyridine (0.5 mmol), LiCl (0.5 mmol),cesium carbonate (1 mmol), and terminal alkyne (1.0 mmol)in DMF (3 mL) was stirred for designated period at 150 C.The reaction mixture was filtered, and neutralized with saturatedNH4Cl solution, followed by extraction with ethyl acetate.The crude product was purified by columnchromatography with the use of hexane and ethyl acetate aseluents.The following compounds were prepared with abovedescribed general procedure.

Reference： [1]Bulletin of the Korean Chemical Society,2015,vol. 36,p. 211 - 218

51
[ 13466-43-8 ]
[ 928-90-5 ]
4-(hydroxybutyl)furo[2,3-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With 5%-palladium/activated carbon; caesium carbonate; lithium chloride; In N,N-dimethyl-formamide; at 150℃; for 22h;	General procedure: In a pressure tube, a suspension of 5% Pd/C (5 mol%), 2-bromo-3-hydroxypyridine (0.5 mmol), LiCl (0.5 mmol),cesium carbonate (1 mmol), and terminal alkyne (1.0 mmol)in DMF (3 mL) was stirred for designated period at 150 C.The reaction mixture was filtered, and neutralized with saturatedNH4Cl solution, followed by extraction with ethyl acetate.The crude product was purified by columnchromatography with the use of hexane and ethyl acetate aseluents.The following compounds were prepared with abovedescribed general procedure.

Reference： [1]Bulletin of the Korean Chemical Society,2015,vol. 36,p. 211 - 218

52
[ 928-90-5 ]
[ 151978-58-4 ]

Reference： [1]Organic Letters,2015,vol. 17,p. 1754 - 1757

53
[ 928-90-5 ]
[ 533-58-4 ]
[ 105952-37-2 ]

Yield	Reaction Conditions	Operation in experiment
87%	With potassium carbonate at 60℃; for 1.5h;	2-Phenylbenzofuran (1a); Typical Procedure General procedure: A freshly prepared solution of PdNPs (12.5 mL) was taken up in a 25-mL round-bottomed flask. To this solution K2CO3 (0.276 g, 2 mmol)and Ph3P (0.052 g, 0.2 mmol) were added followed by 2-iodophenol(0.22 g, 1 mmol) and phenylacetylene (0.122 g, 1.2 mmol). Then, themixture was stirred at 60 °C under aerobic conditions. The reactionwas monitored by TLC until complete consumption of phenylacetylene.When the reaction was complete, the solvents were evaporatedand the residue was purified by column chromatography (hexane-EtOAc). Yields for all compounds are calculated after column chromatography.The catalyst could be recycled. The size of the PdNPs afterfour catalytic cycles was found in the range of 12-18 nm by TEM analysisindicating some agglomeration.The reactions of 2-iodophenol or methyl 4-hydroxy-3-iodobenzoatewith arylacetylenes were carried out as given in the typical procedure.However, reactions using alkylacetylenes did not require theuse of Ph3P.
83%	Stage #1: 2-Iodophenol With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; carbon monoxide In dichloromethane for 0.0833333h; Sealed tube; Stage #2: 5-hexyl-1-ol With 1,8-diazabicyclo[5.4.0]undec-7-ene In dichloromethane at 25℃; for 10h;
57%	With potassium phosphate In N,N-dimethyl-formamide at 160℃; Schlenk technique; Inert atmosphere; Glovebox; Green chemistry;	2.3. Typical procedure for one-pot tandem reaction between o-iodophenolsand terminal alkynes General procedure: General produce: o-iodophenol (0.5 mmol), alkyne (1.0 mmol) andbase (1.0 mmol) were added into a 10 mL dry Schlenk tube under Ar,then anhydrous DMF (5 mL) was injected into the mixture using syringe.Then the solution stirred at preheated oil bath (160 °C). The reactionwas monitored by TLC and GC.The mixture was cooled down toroom temperature after full conversion, then diluted with dichloromethaneand washed with water three times. The organic layerwas separated and washed with brine followed by drying with anhydrousNa2SO4. The filtrate was concentrated in vacuo to afford thecrude product, which was purified by flash column chromatography onsilica gel (petroleum ether).

Reference： [1]Mandali, Pavan Kumar; Chand, Dillip Kumar [Synthesis, 2015, vol. 47, # 11, p. 1661 - 1668]
[2]Xiang, Kuirong; Tong, Pei; Yan, Baorun; Long, Lingling; Zhao, Chunbo; Zhang, Yuan; Li, Ying [Organic Letters, 2019, vol. 21, # 2, p. 412 - 416]
[3]Ji, Guijie; Duan, Yanan; Zhang, Shaochun; Yang, Yong [Catalysis Today, 2019, p. 101 - 108]

54
[ 928-90-5 ]
[ 15126-06-4 ]
methyl 2-(4-hydroxybutyl)benzofuran-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With potassium carbonate; triphenylphosphine; at 60℃; for 1h;	General procedure: A freshly prepared solution of PdNPs (12.5 mL) was taken up in a 25-mL round-bottomed flask. To this solution K2CO3 (0.276 g, 2 mmol)and Ph3P (0.052 g, 0.2 mmol) were added followed by 2-iodophenol(0.22 g, 1 mmol) and phenylacetylene (0.122 g, 1.2 mmol). Then, themixture was stirred at 60 C under aerobic conditions. The reactionwas monitored by TLC until complete consumption of phenylacetylene.When the reaction was complete, the solvents were evaporatedand the residue was purified by column chromatography (hexane-EtOAc). Yields for all compounds are calculated after column chromatography.The catalyst could be recycled. The size of the PdNPs afterfour catalytic cycles was found in the range of 12-18 nm by TEM analysisindicating some agglomeration.The reactions of 2-iodophenol or <strong>[15126-06-4]methyl 4-hydroxy-3-iodobenzoate</strong>with arylacetylenes were carried out as given in the typical procedure.However, reactions using alkylacetylenes did not require theuse of Ph3P.

Reference： [1]Synthesis,2015,vol. 47,p. 1661 - 1668

55
[ 24134-09-6 ]
[ 928-90-5 ]
6-(1,2-dimethyl-1H-imidazol-5-yl)hex-5-yn-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
127 mg	With piperidine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In N,N-dimethyl-formamide; at 80℃; for 3h;Inert atmosphere;	General procedure: To a solution of 2-disubstituted 1-methyl-1H-imidazole 1 (1 mmol) in DMF (5 mL), NBS(169 mg, 0,95 mmol) was added and the resulting reaction mixture was stirred in the dark at room temperature for 3h. Then, Pd(PPh3)2Cl2 (14 mg, 0.02 mmol, 2 mol%), CuI (8 mg, 0.04mmol, 4 mol%), an alkyne 3 (1,1 mmol) and piperidine (300 muL, 255 mg, 3 mmol) were added and the resulting reaction mixture was stirred at 80C (when trimethylsilylacetylene was employed as the alkyne, the reaction was carried out at 50C) for 3 h. The reaction mixture was diluted with EtOAc (100 mL), then saturated aqueous NH4Cl (100 mL) was added. The resulting mixture was stirred for 30 minutes and extracted with EtOAc (3x 25mL). The organic extracts were washed with water (3 x 25 mL) and brine (1 x 25 mL), driedover anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatogaraphy on silica gel. This procedure was employed to prepare compounds 4a-l. GLC analysis showed that all these compounds had chemical purity higherthan 98%.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 3855 - 3857

56
[ 928-90-5 ]
[ 96289-13-3 ]
[ 6968-11-2 ]
C₂₈H₃₆N₂O₉S₂ [ No CAS ]

Reference： [1]RSC Advances,2015,vol. 5,p. 54301 - 54303

57
[ 13392-69-3 ]
[ 928-90-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 1419 - 1427

58
[ 928-90-5 ]
[ 7025-06-1 ]
6-(2-phenoxyphenyl)hex-5-yn-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 70℃;Inert atmosphere;	General procedure: Toasolutionofbromide12(a-c)(0.3mmol)and bis(triphenylphosphine)palladium(II)dichloride(9mumol),N-ethyl-N-isopropylpropan-2-amine(0.3mmol)andcopper(I)iodide(0.03mmol)inDMF(1.5ml)wasaddedtheappropriatealkynerelatedalkyne(0.45mmol)andthevesselwasflushedwithargon,sealedandheated(70°C,overnight).Theresultingdarkmixturewascooledtoroomtemperatureandpurifiedbysilicagelchromatographytoafford13(a-d).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 5009 - 5012

59
[ 928-90-5 ]
[ 15252-45-6 ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 13076 - 13081
[2]Bulletin of the Chemical Society of Japan,2017,vol. 90,p. 298 - 305
[3]Bulletin of the Chemical Society of Japan,2017,vol. 90,p. 387 - 394
[4]ACS Medicinal Chemistry Letters,2021,vol. 12,p. 1759 - 1765

60
[ 928-90-5 ]
[ 102169-54-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: pyridine / dichloromethane / 0 h / 18 °C 2.1: sodium azide / N,N-dimethyl-formamide; diethyl ether / 0.08 h / 20 °C 2.2: 5.5 h 2.3: pH 1
	Multi-step reaction with 2 steps 1.1: di-isopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 0 - 20 °C 2.1: hydrazine hydrate / methanol / 2 h / 80 °C 2.2: 25 - 80 °C

Reference： [1]Nie, Feilin; Kunciw, Dominique L.; Wilcke, David; Stokes, Jamie E.; Galloway, Warren R. J. D.; Bartlett, Sean; Sore, Hannah F.; Spring, David R. [Angewandte Chemie - International Edition, 2016, vol. 55, # 37, p. 11139 - 11143][Angew. Chem., 2016, vol. 128, p. 11305 - 11309,5]
[2]Nilsson, Bradley L.; Overman, Larry E.; De Alaniz, Javier Read; Rohde, Jason M. [Journal of the American Chemical Society, 2008, vol. 130, # 34, p. 11297 - 11299]

61
[ 928-90-5 ]
[ 573-46-6 ]
(4-fluorophenyl)(2-(6-hydroxyhex-1-yn-1-yl)phenyl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	Stage #1: (2-bromophenyl)(4-fluorophenyl)methanone With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine at 20℃; for 0.5h; Sealed tube; Inert atmosphere; Stage #2: 5-hexyl-1-ol at 85℃; for 48h; Sealed tube; Inert atmosphere;

Reference： [1]Akkachairin, Bhornrawin; Tummatorn, Jumreang; Supantanapong, Nantamon; Nimnual, Phongprapan; Thongsornkleeb, Charnsak; Ruchirawat, Somsak [Journal of Organic Chemistry, 2017, vol. 82, # 7, p. 3727 - 3740]

62
[ 13965-03-2 ]
[ 928-90-5 ]
(S)-methyl 5-amino-4-(4-bromo-1-oxoisoindolin-2-yl)-5-oxopentanoate [ No CAS ]
(S)-methyl 5-amino-4-(4-(6-hydroxyhex-1-yn-1-yl)-1-oxoisoindolin-2-yl)-5-oxopentanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%		A solution of (S)-methyl 5-amino-4-(4-bromo-l-oxoisoindolin-2-yl)-5-oxopentanoate (6.93 g) in DMF (40 mL) and Et3N (40 mL). Nitrogen was bubbled through the mixture for 25 minutes. The mixture was split equally into 4 giving (S)-methyl 5-amino-4-(4-bromo-l- oxoisoindolin-2-yl)-5-oxopentanoate (1.732 g, 4.88 mmol) in DMF (10 mL) and triethylamine (10 mL) per vial. Each vial was treated with hex-5-yn-l-ol (0.80 mL, 7.38 mmol) and copper(l) iodide (0.048 g, 0.252 mmol). Nitrogen was again bubbled through the reaction mixtures for 2 minutes. To each was added bis(triphenylphosphine) palladium(ll) dichloride (0.176 g, 0.251 mmol) and the sealed reaction mixtures were heated at 80C overnight. The reaction mixture was concentrated under reduced pressure and the residue was absorbed onto silica gel. Purification via chromatography (ISCO Combiflash, 80 g column, 60 ml/min, 0-78.4% (3:1 EtOAc / EtOH) / hexanes over 30minutes). The product fractions were collected and concentrated under reduced pressure to yield the title compound (1.72 g, 4.61 mmol, 94%) as an orange oil. LC/MS: RT= 0.68 min, m/z = 373.1.

Reference： [1]Patent: WO2017/46036,2017,A1 .Location in patent: Page/Page column 64; 65

63
[ 928-90-5 ]
[ 40140-16-7 ]
3-(4-methoxyphenyl)-7a-methyl-5,6-dihydro-4H-furo[2,3-b]pyran-2(7aH)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With silver trifluoromethanesulfonate In 1,2-dichloro-ethane at 80℃; for 4h; Inert atmosphere;

Reference： [1]Thorat, Sagar S.; Kataria, Priyanka; Kontham, Ravindar [Organic Letters, 2018, vol. 20, # 3, p. 872 - 875]

64
[ 928-90-5 ]
[ 70091-75-7 ]
7a-methyl-3-(4-nitrophenyl)-5,6-dihydro-4H-furo[2,3-b]pyran-2(7aH)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%	With silver trifluoromethanesulfonate In 1,2-dichloro-ethane at 80℃; for 4h; Inert atmosphere;

Reference： [1]Thorat, Sagar S.; Kataria, Priyanka; Kontham, Ravindar [Organic Letters, 2018, vol. 20, # 3, p. 872 - 875]

65
[ 928-90-5 ]
[ 14437-03-7 ]
C₁₅H₁₉NO₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; hexane; at 25℃; for 3h;Inert atmosphere;	(a) In a 100 mL three-vial flask,5-hexyn-1-ol (1.5 mL, 13.6 mmol) was added in sequence,THF 30mL,Methyl N-(p-tosyl)carbamate I (3.27 g, 14.28 mmol),Replace nitrogen 3 times,PPh3 (3.93 g, 14.96 mmol) was added in that order.Diethyl azodicarboxylate (ie DEAD, 6.80 mL of 2.2M n-hexane, 14.96 mmol),Stir at 25°C for 3 hours and the reaction is complete.The reaction solution was concentrated to dryness, and the target product 1 was obtained by column chromatography (PE/EA=1/0 to 6/1, PE was petroleum ether, EA was ethyl acetate) (4.12 g, yield: 98percent).

Reference： [1]Patent: CN107118180,2017,A .Location in patent: Paragraph 0020; 0033

66
[ 928-90-5 ]
[ 152873-79-5 ]
6,6'-(naphthalene-1,5-diyl)bis(hex-5-yn-1-ol) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In dichloromethane at 20℃; for 12h; Inert atmosphere;	6,6'-(naphthalene-1,5-diyl)bis(hex-5-yn-1-ol) S3a A dried 100 ml round-bottomed flask was charged with naphthalene-1,5-diyl bis(trifluoromethanesulfonate) (S3) (0.800 g, 1.89 mmol), PdCl2[P(C6H5)3]2 (66.2 mg, 0.09 mmol, 5.0 mol%), CuI (18.0 mg, 0.09 mmol, 5 mol%) under argon atmosphere, 5-hexyn-1-ol (0.53 mL, 4.71 mmol) was injected, then CH2Cl2/Et3N (10 ml/3 ml) was added, the resultant solution was stirred at room temperature for 12 hours. 1M hydrochloric acid solution was added and mixture extracted with dichloromethane. The combined organic layer was washed with water and dried over MgSO4. Solvent was removed by rotary evaporator after filtration. The residue was purified by column chromatography using a mixture of ethyl acetate/hexane (2/1) and furnished the product 6,6'-(naphthalene-1,5-diyl)bis(hex-5-yn-1-ol) (S3a) (451.1 mg, 74%) as white solids. 1H NMR (400 MHz, CDCl3): δ = 1.80-1.84 (m, 8H), 2.62 (t, J = 6.4 Hz, 4H), 3.75 (t, J = 6.0 Hz, 4H), 7.46 (dd, J = 8.0, 7.2 Hz, 2H), 7.63 (d, J = 6.8 Hz, 2H), 7.63 (d, J = 8.8 Hz, 2H). ; 13C NMR (100 MHz, CDCl3): δ = 19.5, 25.2, 32.0, 62.5, 78.9, 95.2, 121.9, 125.8, 126.3, 130.5, 133.3. ; IR(NaCl, Cm-1) : 3346, 2936, 2360, 1582, 1412, 1345, 1039, 780. ; HRMS (ESI) [M + Na]+ calculated for C22H24O2Na+ : 343.1669, found 343.1672.

Reference： [1]Lee, Kyu Hwan; Jillella, Raveendra; Kim, Jaewoong; Oh, Chang Ho [Bulletin of the Korean Chemical Society, 2018, vol. 39, # 5, p. 651 - 656]

67
[ 928-90-5 ]
[ 151391-00-3 ]
6,6'-(naphthalene-2,7-diyl)bis(hex-5-yn-1-ol) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In dichloromethane; at 20℃; for 12h;Inert atmosphere;	A dried 100 ml round-bottomed flask was charged with naphthalene-2,7-diyl bis(trifluoromethanesulfonate) (S4) (1.300 g, 3.06 mmol), PdCl2[P(C6H5)3]2 (107.5 mg, 0.15 mmol, 5.0 mol%), CuI (29.2 mg, 0.15 mmol, 5 mol%) under argon atmosphere, 5-hexyn-1-ol (0.85 mL, 7.66 mmol) was injected, then CH2Cl2/Et3N (20 ml/4 ml) was added, the resultant solution was stirred at room temperature for 12 hours. 1M hydrochloric acid solution was added and mixture extracted with dichloromethane. The combined organic layer was washed with water and dried over MgSO4. Solvent was removed by rotary evaporator after filtration. The residue was purified by column chromatography using a mixture of ethyl acetate/hexane (2/1) and furnished the product 6,6'-(naphthalene-2,7-diyl)bis(hex-5-yn-1-ol) (S4a) (0.812 g, 83%) as white solids. 1H NMR (400 MHz, CDCl3): δ = 1.71-1.81 (m, 8H), 2.51 (t , J = 6.4 Hz, 4H), 3.74 (t, J = 6.4 Hz, 4H), 7.42 (dd, J = 8.4, 1.2 Hz, 2H), 7.69 (d, J = 8.4 Hz, 2H), 7.81 (s, 2H). ; 13C NMR (100 MHz, CDCl3): δ = 19.3, 25.0, 31.9, 62.5, 81.1, 90.7, 121.8, 127.6, 129.1, 130.6, 131.5, 132.7. ; IR(NaCl, Cm-1) : 3302, 2950, 2360, 1598, 1429, 1327, 1066, 846. ; HRMS (ESI) [M + Na]+ calculated for C22H24O2Na+ : 343.1669, found 343.1672.

Reference： [1]Bulletin of the Korean Chemical Society,2018,vol. 39,p. 651 - 656

68
[ 928-90-5 ]
[ 128406-10-0 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
56%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In dichloromethane at 20℃; for 12h; Inert atmosphere;	6,6'-((9H-fluorene-9,9-diyl)bis(4,1-phenylene))bis(hex-5-yn-1-ol) S5a A dried 100 ml round-bottomed flask was charged with 9,9-bis(4-bromophenyl)-9H-fluorene (S5) (1.200 g, 2.52 mmol), PdCl2[P(C6H5)3]2 (88.4 mg, 0.13 mmol, 5.0 mol%), CuI (24.0 mg, 0.13 mmol, 5 mol%) under argon atmosphere, 5-hexyn-1-ol (0.70 mL, 6.30 mmol) was injected, then CH2Cl2/Et3N (20 ml/4 ml) was added, the resultant solution was stirred at room temperature for 12 hours. 1M hydrochloric acid solution was added and mixture extracted with dichloromethane. The combined organic layer was washed with water and dried over MgSO4. Solvent was removed by rotary evaporator after filtration. The residue was purified by column chromatography using a mixture of ethyl acetate/hexane (2/1) and furnished the product 6,6'-((9H-fluorene-9,9-diyl)bis(4,1-phenylene))bis(hex-5-yn-1-ol) (S5a) (0.720 g, 56%) as white solids. 1H NMR (400 MHz, CDCl3): δ = ; 1.66-1.52 (m, 8H), 2.35 (t, J = 6.4 Hz, 4H), 3.62 (t, J = 6.4 Hz, 4H), 7.01 (d, J = 6.8 Hz, 4H), 7.31-7.15 (m, 10H), 7.68 (d, J = 7.6 Hz, 2H). ; 13C NMR (100 MHz, CDCl3): δ = 19.2, 25.0, 31.9, 62.5, 80.7, 90.0, 120.2, 122.3, 126.0, 127.7, 127.8, 128.0, 131.4, 140.1, 145.1, 150.5. ; IR(NaCl, Cm-1) : 3354, 2938, 2360, 1502, 1445, 1332, 1061, 827. ; HRMS (ESI) [M + Na]+ calculated for C37H34O2Na+ : 533.2452, found 533.2455.

Reference： [1]Lee, Kyu Hwan; Jillella, Raveendra; Kim, Jaewoong; Oh, Chang Ho [Bulletin of the Korean Chemical Society, 2018, vol. 39, # 5, p. 651 - 656]

69
[ 928-90-5 ]
[ 60186-89-2 ]
C₁₂H₁₆N₂O₃ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2018,vol. 140,p. 6027 - 6032

70
[ 928-90-5 ]
[ 73852-88-7 ]
6-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)hex-5-yn-1-ol [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2018,vol. 140,p. 7074 - 7078

71
[ 928-90-5 ]
[ 40738-83-8 ]
5-(6-hydroxyhex-1-yn-1-yl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2018,vol. 140,p. 7074 - 7078

72
[ 112-54-9 ]
[ 928-90-5 ]
(R)-octadeca-5,6-dien-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With (S)-(-)-2-(1-hydroxy-1-methylethyl)-pyrrolidine; copper(ll) bromide In 1,4-dioxane at 130℃; for 12h; Inert atmosphere; Schlenk technique; Sealed tube; enantioselective reaction;	Synthesis of (R)-Pentadeca-2,3-dien-1-ol [(R)-4aa] Using (S)-3b; Typical Procedure I General procedure: To a flame-dried Schlenk tube with a polytetrafluoroethylene plug were added CuBr2 (0.0453 g, 0.2 mmol), (S)-3b (0.1299 g, 1.0 mmol), prop-2-yn-1-ol (1a; 0.0846 g, 1.5 mmol, dissolved in 1.5 mL of 1,4- dioxane), and dodecanal (2a; 0.2762 g, 1.5 mmol, dissolved in 1.5 mL of 1,4-dioxane) sequentially under N2. The Schlenk tube was then sealed by screwing the polytetrafluoroethylene plug tightly with the outlet being closed. Then the reaction mixture was heated in an oil bath preheated at 130 °C with stirring. After 12 h, the reaction was complete as monitored by TLC and the mixture was cooled to r.t. Afterwards, the resulting mixture was diluted with Et2O (30 mL) and washed with aq HCl (3 M, 20 mL). The organic layer was separated and the aqueous layer was extracted with Et2O (3 × 15 mL). The combined organic layers were washed with brine (20 mL) and dried (anhyd Na2SO4). After filtration and evaporation, the residue was purified by chromatography on silica gel (PE/EtOAc 8:1, 720 mL) to afford (R)- 4aa;9a yield: 0.1372 g (61%);

Reference： [1]Ma, Dengke; Duan, Xinyu; Fu, Chunling; Huang, Xin; Ma, Shengming [Synthesis, 2018, vol. 50, # 13, p. 2533 - 2545]

73
[ 928-90-5 ]
[ 2169-87-1 ]
di(hex-5-yn-1-yl) naphthalene-2,3-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃;	General procedure: To a stirred solution of the corresponding alcohol and the carboxylic acid in dry dichloromethane(0.2 M) was added EDC.HCl (3 equiv. according to limiting reagent) and 4-dimethylaminopyridine (DMAP, 1 equiv.) at room temperature. The reaction mixture was stirredat room temperature and monitored by TLC. Upon the complete conversion of the startingmaterial, the crude reaction mixture was washed by H2O and Brine. The organic layer was driedby Mg2SO4. The solvent was removed under reduced pressure and the residue was purified byflash chromatography on silica gel to give desired product.

Reference： [1]Chem,2018,vol. 4,p. 1983 - 1993

74
[ 928-90-5 ]
[ 2169-87-1 ]
C₂₄H₂₂O₄ [ No CAS ]

Reference： [1]Chem,2018,vol. 4,p. 1983 - 1993

75
[ 928-90-5 ]
[ 533-58-4 ]
[ 1864-94-4 ]
[ 105952-37-2 ]
3',4',5',6'-tetrahydrospiro[chromane-2,2'-pyran]-4-one [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 412 - 416

76
[ 928-90-5 ]
[ 201230-82-2 ]
[ 38941-98-9 ]
6-(tert-butyl)-3',4',5',6'-tetrahydrospiro[chromane-2,2'-pyran]-4-one [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 412 - 416

77
[ 928-90-5 ]
[ 201230-82-2 ]
[ 207115-22-8 ]
6-bromo-3',4',5',6'-tetrahydrospiro[chromane-2,2'-pyran]-4-one [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 412 - 416

78
[ 928-90-5 ]
[ 201230-82-2 ]
[ 2713-29-3 ]
6-fluoro-3',4',5',6'-tetrahydrospiro[chromane-2,2'-pyran]-4-one [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 412 - 416

79
[ 928-90-5 ]
[ 16954-05-5 ]
6,6'-(1,2-dimethyl-1H-imidazol-4,5-diyl)bis(hex-5-yn-1-ol) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With dichloro bis(acetonitrile) palladium(II); copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 80℃; for 3h; Inert atmosphere;	Symmetrical 1,2-Disubstituited 4,5-Dialkynyl-1H-imidazoles 5, 9, and 10; General Procedure General procedure: A solution of 4,5-dibromo-1,2-disubstituted-1H-imidazole 2, 7a-e, or 8a (1 mmol) or 5-alkynyl-4-bromo-1,2-dimethyl-1H-imidazole, alkyne 3 (3 mmol or 1.5 mmol), Pd(MeCN)2Cl2 (10 mg, 0.04 mmol, 4 mol%), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (26 mg, 0.04 mmol, 4 mol%), and CuI (3 mg, 0.02 mmol, 2 mol%) in DMF (4.5 mL) and DBU (0.5 mL) was stirred at 80 °C for 3 h. The reaction mixture was then diluted with EtOAc (100 mL) and sat. aq NH4Cl (100 mL) was added. The resulting mixture was stirred in the open air for 0.5 h and then extracted with EtOAc. The combined organic extractswere washed with H2O (3 25 mL) and brine (25 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel. This procedure was employed to prepare 1,2-dimethylimidazole-fused enediynes 5a-e, 2-aryl-1-methylimidazole-fused enediynes 9a-d, and 1,2-diarylimidazole-fused enediyne 10a (Table 2).

Reference： [1]Lessi, Marco; Panattoni, Alessandro; Guglielmero, Luca; Minei, Pierpaolo; Bellina, Fabio [Synthesis, 2019, vol. 51, # 4, p. 933 - 943]

80
[ 928-90-5 ]
[ 16954-05-5 ]
6,6'-(1,2-dimethyl-1H-imidazol-4,5-diyl)bis(hex-5-yn-1-ol) [ No CAS ]
6-(4-bromo-1,2-dimethyl-1H-imidazol-5-yl)hex-5-yn-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With 1,1'-bis-(diphenylphosphino)ferrocene; dichloro bis(acetonitrile) palladium(II); copper(l) iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 80℃; for 3h; Inert atmosphere; regioselective reaction;	5-Alkynyl-4-bromo-1,2-dimethyl-1H-imidazoles 4; General Procedure General procedure: A solution of 4,5-dibromo-1,2-dimethyl-1H-imidazole (2; 254 mg, 1 mmol), alkyne 3 (1.5 mmol), Pd(MeCN)2Cl2 (10 mg, 0.04 mmol, 4 mol%), 1,1'-bis(diphenylphosphino)ferrocene (22 mg, 0.04 mmol, 4 mol%), and CuI (3 mg, 0.02 mmol, 2 mol%) in DMF (4.5 mL) and DBU (0.5 mL) was stirred at 80 °C for 3h. The reaction mixture was then diluted with EtOAc (100 mL) and sat. aq NH4Cl (100 mL) was added. The resulting mixture was stirred in the open air for 0.5 h and then extracted with EtOAc. The combined organic extracts were washed with H2O (3 25 mL) and brine (25 mL), dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel. This procedure was employed to prepare compounds 4a-e (Table 3).

Reference： [1]Lessi, Marco; Panattoni, Alessandro; Guglielmero, Luca; Minei, Pierpaolo; Bellina, Fabio [Synthesis, 2019, vol. 51, # 4, p. 933 - 943]

81
[ 928-90-5 ]
[ 3197-44-2 ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 9994 - 9997
Angew. Chem.,2019,vol. 131,p. 10099 - 10102,4

82
[ 928-90-5 ]
[ 81-23-2 ]
C₃₀H₄₃ClO₅ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2020,vol. 59,p. 2904 - 2910
Angew. Chem.,2020,vol. 132,p. 2926 - 2932,7

83
[ 928-90-5 ]
[ 81-23-2 ]
hex-5-yn-1-yl (4R)-4-((10S,13R)-10,13-dimethyl-3,7,12-trioxohexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoate [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2020,vol. 59,p. 2904 - 2910
Angew. Chem.,2020,vol. 132,p. 2926 - 2932,7

84
[ 928-90-5 ]
[ 6937-16-2 ]
ethyl 4-(hex-5-yn-1-ylamino)butanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
8%		a) Ethyl 4-(hex-5-yn-1-ylamino)butanoate (41) A solution of sulfur trioxide pyridine complex (4.87 g, 30.6 mmol) and pyridine (2.53 ml_, 30.6 mmol) in CH2CI2 (10 ml.) was stirred at rt for 5 min. To this solution was added DIPEA (5.33 ml_, 30.6 mmol) and DMSO (7.24 ml_, 102 mmol) and stirred at rt for 5 min. The mixture was cooled to -40 C and to this was added 5-heyn-1 -ol (1.00 g, 10.2 mmol). The reaction was stirred for 2 h at -40 C, followed by 1 h at -10 C then 1 h at rt. Upon completion, the reaction was acidified to pH 3 with 1 M HCI and diluted with CH2CI2 (10 ml_). The layers were separated and the aqueous phase was extracted with further CH2CI2 (2 c 20 ml_). The combined organic fractions were washed with brine (2 x 50 ml_), dried (MgS04) and concentrated in vacuo. The crude oil was immediately redissolved in MeOH (10 ml_). To this solution was added ethyl 4-aminobutyrate hydrochloride (2.05 g, 12.2 mmol) and triethylamine (2.84 ml_, 20.4 mmol) and the mixture stirred at room temperature for 16 h. The reaction mixture was then cooled to 0 C and to this was added sodium borohydride (578 mg, 15.3 mmol). The reaction was warmed to rt and stirred for 2 h. Upon completion, the reaction mixture was concentrated in vacuo, redissolved in CH2CI2 and quenched with H2O. The layers were separated and the aqueous phase extracted with further CH2CI2 (3 x 15 ml_), dried (MgS04) and concentrated in vacuo. The crude residue was purified by FCC (0- 7.5% MeOH/ CH2CI2) to yield ethyl 4-(hex-5-yn-1-ylamino)butanoate (175 mg, 0.828 mmol, 8%) as a clear oil.

Reference： [1]Patent: WO2020/25108,2020,A1 .Location in patent: Page/Page column 51-52

85
[ 928-90-5 ]
[ 18162-48-6 ]
[ 61362-77-4 ]

Reference： [1]Chemistry - A European Journal,2020,vol. 26,p. 2808 - 2812

86
[ 76334-36-6 ]
[ 928-90-5 ]
C₁₀H₁₆O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 20℃; for 5h;

Reference： [1]Lee, Jaeyeon; Kim, Jiheon; Lee, Hee-Yoon [Organic Letters, 2020, vol. 22, # 11, p. 4073 - 4077]

87
[ 354-08-5 ]
[ 928-90-5 ]
C₈H₉BrF₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96.9%	With phosphoric acid; sulfuric acid In 5,5-dimethyl-1,3-cyclohexadiene at 120℃; for 5h;	4 Example 4 Add 87.5 grams of 2-bromo-2,2-difluoroacetic acid, 98 grams of 5-hexyn-1-ol, 1.5 grams of sulfuric acid, 1L reaction vessel equipped with a thermometer, reflux condenser, water separator and agitator.1.5 grams of phosphoric acid and 500 grams of xylene are reacted at 120°C until no water is released.The reaction time is 5 hours. After the reaction is completed, the solvent and excess 5-hexyn-1-ol are recovered by distillation,Then vacuum distillation collects the distillate under the condition of 165166/40mmHg,123.5 g of propargyl hexyl 2-bromo-2,2-difluoroacetate was obtained, the yield was 96.9%, and the purity was 99.8%.

Reference： [1]Current Patent Assignee: TRANSFAR GROUP CO. LTD.; ZHEIJIANG TRANSFAR FUNCTIONAL NEW MAT; ZHEJIANG TRANSFAR FUNCTIONAL NEW MATERIAL; ZHEJIANG TRANSFAR FUNCTIONAL NEW MAT; HANGZHOU NORMAL UNIVERSITY - CN112608236, 2021, A Location in patent: Paragraph 0044-0045

88
[ 1010100-26-1 ]
[ 928-90-5 ]
3-(5-(6-hydroxyhex-1-yn-1-yl)-1-oxoisoindolin-2-yl)piperidine-2,6-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72.2%	With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; copper (I) iodide; triethylamine In N,N-dimethyl-formamide at 70℃; for 5h; Inert atmosphere;	1 Step 1: [0402] Compound C192-1 (100 mg, 0.31mmol), compound C192-2 (76 mg,0.78mmol), cuprous iodide (12 mg, 0.06mmol), Pd(dppf)Cl2 (87 mg, 0.12mmol) and triethylamine (94 mg, 0.93mmol) were dissolved in 4 mL of anhydrous DMF. The mixture was reacted with stirring at 70°C under nitrogen protection for 5h. The solvent was removed under reduced pressure. The crude product was purified by thin layer chromatography to afford off-white solid compound C192-3 (78 mg, yield: 72.2%). LCMS: [M + H]+ = 341.
	With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide In N,N-dimethyl-formamide at 80℃; Inert atmosphere;

Reference： [1]Current Patent Assignee: BEIJING TIDE PHARMACEUTICAL CO LTD; SINO BIOPHARMACEUTICAL LIMITED; BEIJING TEDE PHARMACEUTICAL - EP4019021, 2022, A1 Location in patent: Paragraph 0401-0402
[2]Lu, Jibu; Huang, Yongjun; Huang, Jing; He, Rui; Huang, Minhao; Lu, Xiaoyun; Xu, Yong; Zhou, Fengtao; Zhang, Zhang; Ding, Ke [Journal of Medicinal Chemistry, 2022, vol. 65, # 3, p. 2313 - 2328]

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P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 928-90-5 ] {[proInfo.proName]}

Quality Control of [ 928-90-5 ]

Related Doc. of [ 928-90-5 ]

Product Details of [ 928-90-5 ]

Calculated chemistry of [ 928-90-5 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 928-90-5 ]

Application In Synthesis of [ 928-90-5 ]

[ 928-90-5 ] Synthesis Path-Upstream 1~24

[ 928-90-5 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 928-90-5 ]

Alkynes

Aliphatic Chain Hydrocarbons

Alcohols

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

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[ 928-90-5 ]