[ CAS No. 30964-00-2 ] {[proInfo.proName]}

Name: 30964-00-2|6-Heptynoic acid|95%
Brand: Ambeed
SKU: A650746
Rating: 90 (26 reviews)

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Quality Control of [ 30964-00-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 30964-00-2 ]

Product Details of [ 30964-00-2 ]

CAS No. :	30964-00-2	MDL No. :	MFCD00239430
Formula :	C₇H₁₀O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OFCPMJGTZUVUSM-UHFFFAOYSA-N
M.W :	126.15	Pubchem ID :	4377950
Synonyms :

Calculated chemistry of [ 30964-00-2 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.57
Num. rotatable bonds :	4
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	35.7
TPSA :	37.3 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) :	-6.22 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.66
Log Po/w (XLOGP3) :	1.2
Log Po/w (WLOGP) :	1.34
Log Po/w (MLOGP) :	1.52
Log Po/w (SILICOS-IT) :	1.18
Consensus Log Po/w :	1.38

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-1.11
Solubility :	9.7 mg/ml ; 0.0769 mol/l
Class :	Very soluble
Log S (Ali) :	-1.58
Solubility :	3.32 mg/ml ; 0.0263 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.91
Solubility :	15.4 mg/ml ; 0.122 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.17

Safety of [ 30964-00-2 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P264-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P321-P363-P405-P501	UN#:	3265
Hazard Statements:	H314	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 30964-00-2 ]

* 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 [ 30964-00-2 ]
Downstream synthetic route of [ 30964-00-2 ]

[ 30964-00-2 ] Synthesis Path-Upstream 1~1

1
[ 30964-00-2 ]
[ 506-26-3 ]

Reference： [1] Synthesis, 1998, # 7, p. 1015 - 1018
[2] Chemistry and Industry (London, United Kingdom), 1959, p. 1288[3] Journal of the Chemical Society, 1961, p. 2779,2786
[4] Journal of the Chemical Society, 1961, p. 2779,2783
[5] Proceedings of the Chemical Society, London, 1960, p. 221

[ 30964-00-2 ] Synthesis Path-Downstream 1~68

1
[ 64-17-5 ]
[ 30964-00-2 ]
[ 105339-02-4 ]

Yield	Reaction Conditions	Operation in experiment
92%	With sulfuric acid for 3h; Inert atmosphere; Reflux;	Ethyl hept-6-ynoate (14) To an oven-dried 20 mL round-bottomed flask outfitted with a stir bar, a condenser, a gas inlet adapter and a rubber septum, absolute ethanol (5.0 mL), hept-6-ynoic acid (13) (99.7 mg, 0.790 mmol) and concentrated H2SO4 (1 drop) were added sequentially. The mixture was refluxed for 3 h before cooling to room temperature and the solvent removed under reduced pressure. The crude product was diluted with diethyl ether (50 mL), washed with saturated NaHCO3 (5 mL) and water (5 mL). The organic layers were dried over magnesium sulfate, filtered and the solvent removed under reduced pressure. The residue was then purified by flash silica gel chromatography (pet. ether/Et2O = 10/1) to afford the title compound 14 (112 mg, 92%) as a colourless oil. Rf: 0.43 (pet. ether/EtOAc = 5:1). 1H NMR (500 MHz, CDCl3): δ 4.13 (q, J = 7.1 Hz, 2H), 2.32 (t, J = 7.4 Hz, 2H), 2.21 (td, J = 7.0, 2.6 Hz, 2H), 1.95 (t, J = 2.7 Hz, 1H), 1.79-1.71 (m, 2H), 1.60-1.53 (m, 2H), 1.25 (t, J = 7.1 Hz, 3H). 13C NMR (125 MHz, CDCl3): δ 173.4, 84.0, 68.6, 60.3, 33.8, 27.9, 24.0, 18.1, 14.3. These characterization data match those reported in the literature [56,57].
83%	With sulfuric acid for 3h; Reflux; Inert atmosphere;
70%	With sulfuric acid Heating;

	With sulfuric acid
	With sulfuric acid for 2.5h; Heating;

Reference： [1]Xu, Tao; Cuyamendous, Claire; Brown, Sarah L.; Andreassend, Sarah K.; Cumming, Hemi; Evans, Gary B.; Teesdale-Spittle, Paul H.; Harvey, Joanne E. [Tetrahedron, 2021, vol. 88]
[2]Parsons, Scott R.; Hooper, Joel F.; Willis, Michael C. [Organic Letters, 2011, vol. 13, # 5, p. 998 - 1000]
[3]Nakatani; Fukunaga; Haraguchi; et al. [Bulletin of the Chemical Society of Japan, 1986, vol. 59, # 11, p. 3535 - 3539]
[4]Eglinton; Whiting [Journal of the Chemical Society, 1953, p. 3052,3055] Braude et al. [Journal of the Chemical Society, 1956, p. 3070,3073] Goze, Christine; Ulrich, Gilles; Ziessel, Raymond [Journal of Organic Chemistry, 2007, vol. 72, # 2, p. 313 - 322]
[5]Pallerla, Mahesh K.; Fox, Joseph M. [Organic Letters, 2005, vol. 7, # 16, p. 3593 - 3595]

2
[ 30964-00-2 ]
[ 89856-86-0 ]

Yield	Reaction Conditions	Operation in experiment
	With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 1h;Inert atmosphere;	Preparation 3<strong>[30964-00-2]6-Heptynoic acid</strong>, 1,1-dimethylethyl ester8.00 g (63.41 mM) of <strong>[30964-00-2]6-heptynoic acid</strong> were dissolved in a mixture of 137 mL of anhydrous dichloromethane and 0.70 mL of anhydrous dimethylformamide. 16.10 g (126.83 mM) of oxalyl chloride were added dropwise. The reaction mixture was stirred at ambient temperature for 1 hour under a nitrogen atmosphere and then evaporated under a nitrogen atmosphere. The residual product was taken up in 137 mL of tetrahydrofuran. The mixture was cooled to 0 C. and admixed in portions with 14.23 g (126.83 mM) of potassium tert-butoxide. The reaction mixture was held at ambient temperature with stirring for an hour. Then 200 g of ice and 200 mL of water were added. The mixture was extracted with 3 times 200 mL of ether and then the combined organic phases were dried over magnesium sulphate and concentrated under reduced pressure. This gave 7.46 g of the expected compound in the form of a brown oil (yield=65%).1H NMR (DMSO-d6, 250 MHz) delta=1.40 (s, 9H), 1.40-1.45 (m, 4H), 2.13-2.22 (m, 4H), 2.75 (t, J=2.7, 1H).
	With oxalyl dichloride; N,N-dimethyl-formamide; In toluene; at 20℃; for 3h;Inert atmosphere;	Oxalylchloride (518 muL, 5.94 mmol, 1.5 eq.) was added dropwise to a solution of <strong>[30964-00-2]hept-6-ynoic acid</strong> SI61 (0.5 mL, 3.96 mmol) in toluene (19 mL). A catalytic amount of DMF (2 drops) was added and the solution was stirred at room temperature for 3 h. After concentration, the residue was co-evaporated with toluene and the resulting crude hept-6-ynoyl chloride was used without further purification. A 1M solution of hept-6-ynoyl chloride in dichloroethane was made up and 2,4-dimethyl-1H-pyrrole (856 muL, 8.32 mmol, 2.1 eq.) was added. The resulting reaction mixture was stirred at 65 C for 2 h. After cooling to room temperature, BF3?OEt2 (2.45 mL, 19.8 mmol, 5 eq.) was added over 5 min, followed by the dropwise addition of diisopropylethyl amine (2.76 mL, 15.84 mmol, 4 eq.). Argon was then bubbled for 5 min through the solution, and the reaction mixture was stirred for 12 h at room temperature, before being washed with water and extracted with ethyl acetate. The organic phase was dried over MgSO4, filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography (cyclohexane/ethyl acetate 80:20) to give 27 (390 mg, 1.19 mmol , 30 %) as a red oil that slowly crystallizes.; 1H NMR (CDCl3, 300 MHz) delta 6.27 (s, 2H), 3.14-3.09 (2H), 2.75 (s, 6H), 2.62 (s, 6H), 2.51-2.47 (2H), 2.21 (m, 1H), 1.97-1.93 (4H).; 13C NMR (CDCl3, 75 MHz) delta 153.6 (2xC), 145.8 (2xC), 140.3 (2xC), 131.3, 121.5 (2xC), 83.6, 68.9, 30.4, 28.7, 27.6, 18.0 (2xC), 16.1 (2xC), 14.3.; The spectral data are in agreement with those reported in the literature.[21]; 11B NMR (CDCl3, 128 MHz) delta 3.87 (t, J= 33.2 Hz)
	With oxalyl dichloride; N,N-dimethyl-formamide; In toluene; at 20℃; for 3h;	4,4-Difluoro-8-(hept-6-yne)-l,355,7-tetramethyl-4-bora-3a,4a-diaza-s- indacene (27)Oxalylchloride (518 ?, 5.94 mmol, 1.5 eq.) was added dropwise to a solution of <strong>[30964-00-2]hept-6-ynoic acid</strong> SI61 (0.5 mL, 3.96 mmol) in toluene (19 mL). A catalytic amount of DMF (2 drops) was added and the solution was stirred at room temperature for 3 h. After concentration, the residue was co-evaporated with toluene and the resulting crude hept-6-ynoyl chloride was used without further purification. A 1M solution of hept-6-ynoyl chloride in dichloroethane was made up and 2,4-dimethyl-lH-pyrrole (856 ?L, 8.32 mmol, 2.1 eq.) was added. The resulting reaction mixture was stirred at 65 C for 2 h. After cooling to room temperature, BF3*OEt2 (2.45 mL, 19.8 mmol, 5 eq.) was added over 5 min, followed by the dropwise addition of diisopropyl ethyl amine (2.76 mL, 15.84 mmol, 4 eq.). Argon was then bubbled for 5 min through the solution, and the reaction mixture was stirred for 12 h at room temperature, before being washed with water and extracted with ethyl acetate. The organic phase was dried over MgS0 , filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography (cyclohexane/ethyl acetate 80:20) to give 27 (390 mg, 1.19 mmol , 30 %) as a red oil that slowly crystallizes.1H NMR (CDC13, 300 MHz) ? 6.27 (s, 2H), 3.14-3.09 (2H), 2.75 (s, 6H), 2.62 (s, 6H), 2.51-2.47 (2H), 2.21 (m, 1H), 1.97-1.93 (4H).13C NMR (CDCI3, 75 MHz) 6 153.6 (2xC), 145.8 (2xC), 140.3 (2xC), 131.3, 121.5 (2xC), 83.6, 68.9, 30.4, 28.7, 27.6, 18.0 (2xC), 16.1 (2xC), 14.3.The spectral data are in agreement with those reported in the literature.121] "B NMR (CDCI3, 128 MHz) ? 3.87 (t, J = 33.2 Hz)

	With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 3h;Cooling with ice;	<strong>[30964-00-2]6-heptynoic acid</strong> (0.83 g, 6 mmol) was dissolved in 5 mL dry DCM and added a catalytic amount of DMF (1muL). The solution was cooled in an ice bath and oxalyl chloride (0.572 mL, 6.6 mmol) was added atmosphere. The solution was stirred at ambient temperature for 3 hours. DCM was removed in vacou and the heptynoyl chloride was used immediately in the next step without purification.
	With oxalyl dichloride; In dichloromethane;Inert atmosphere; Reflux;	<strong>[30964-00-2]6-Heptynoic acid</strong> (0.10 niL, 0.79 mmol, 1.0 equiv) was dissolved in CH2CI2 (1.6 mL). Then oxalyl chloride (0.40 mL, 4.8 mmol, 6.1 equiv) was added dropwise. The reaction mixture was heated at reflux for 1 hour, or until complete. The reaction mixture was concentrated, and then dissolved in CH2CI2 (5 mL). 4-Amino-2-(trifluoromethyl)pyridine (0.12 g, 0.79 mmol, 1.0 equiv) and pyridine (60 mu,, 0.79 mmol, 1.0 equiv) were added to the solution. The reaction mixture was stirred for 12 h, and was then quenched with NH4C1 (10 mL). The aqueous layer was extracted with CH2CI2 (3 x 10 mL). The combined organic layer was washed sequentially with 1 M HC1 (2 x 10 mL) and brine (20 mL), dried over a2S04 and concentrated, providing S81 in a 75% yield over two steps. S81 was taken onward without further purification. HRMS (ESI-TOF) calculated for C13H14F3 2O [M+H]+: m/z 271.1058, found 271.1048; *H NMR: (500 MHz, CDC13) delta 8.54 (d, J = 5.5 Hz, 1H), 8.51-8.32 (m, 1H), 7.97-7.93 (m, 1H), 7.71-7.67 (m, 1H), 2.45 (t, J = 7.5 Hz, 2H), 2.27-2.18 (m, 2H), 1.99-1.93 (m, 1H), 1.84 (p, J= 7.5 Hz, 2H), 1.58 (p, J= 7.1 Hz, 2H); 13C NMR: (125 MHz, CDC13) 5 172.3, 150.7, 149.0 (q, J= 36 Hz), 146.6, 121.3 (q, J= 274 Hz), 1 15.6, 110.6-110.4 (m),
	With oxalyl dichloride; N,N-dimethyl-formamide; In chloroform-d1; at 0 - 20℃; for 3h;	General procedure: Alkyne acid (1.175mmol) (31-24) was dissolved in deuterated chloroform (2mL) and a catalytic amount of DMF was added (200muL). The solution was cooled to 0C and oxalyl dichloride was added dropwise (1.175mmol, 99muL) and the reaction was stirred at room temperature for 3h. A little amount of reaction was diluted in deuterated chloroform and monitored by 1H NMR. The peaks of desired acyl chlorides (35-38) were shifted from those of the corresponding carboxylic acids. When the conversion was complete, to the reaction were added 1,4-dioxane (5mL), triethylamine (1.959mmol, 273muL) and the 5-amino-pyrazolo-triazolo-pyrimidine 30 (0.392mmol, 100mg). The reaction was stirred at reflux overnight (TLC ethyl acetate 9.5/methanol 0.5) then the solvent was removed under reduced pressure. The residue was dissolved in water and extracted with dichloromethane (3 times), The organic layers were collected and dried over sodium sulfate anhydrous and the solvent removed under reduced pressure. The crude was purified on flash silica column chromatography (ethyl acetate 9.8/methanol 0.2) to afford the desired compound (19-22).

Reference： [1]Journal of general chemistry of the USSR,1962,vol. 32,p. 57 - 62
Zhurnal Obshchei Khimii,1962,vol. 32,p. 58 - 64
[2]Chemische Berichte,1989,vol. 122,p. 1081 - 1088
[3]Organic and Biomolecular Chemistry,2004,vol. 2,p. 3006 - 3017
[4]Carbohydrate Research,2006,vol. 341,p. 705 - 716
[5]Journal of the Chemical Society. Perkin Transactions 2 (2001),2000,p. 2399 - 2409
[6]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 6169 - 6171
[7]Journal of Medicinal Chemistry,2010,vol. 53,p. 1306 - 1318
[8]Patent: US2011/178150,2011,A1 .Location in patent: Page/Page column 6
[9]Chemistry - A European Journal,2011,vol. 17,p. 14413 - 14419
[10]Langmuir,2011,vol. 27,p. 741 - 750
[11]MedChemComm,2013,vol. 4,p. 383 - 386
[12]Patent: EP2594561,2013,A1 .Location in patent: Paragraph 0488-0492
[13]Patent: WO2013/72896,2013,A1 .Location in patent: Page/Page column 107; 108
[14]Chemistry - A European Journal,2013,vol. 19,p. 8388 - 8392
[15]Angewandte Chemie - International Edition,2013,vol. 52,p. 12308 - 12312
Angew. Chem.,2013,vol. 125,p. 12534 - 12538
[16]European Journal of Organic Chemistry,2014,vol. 2014,p. 3347 - 3354
[17]Journal of Organic Chemistry,2014,vol. 79,p. 6330 - 6335
[18]Beilstein Journal of Organic Chemistry,2015,vol. 11,p. 147 - 154
[19]Patent: WO2015/42363,2015,A1 .Location in patent: Paragraph 00399-00400
[20]Journal of Medicinal Chemistry,2015,vol. 58,p. 1298 - 1306
[21]Journal of the American Chemical Society,2015,vol. 137,p. 7087 - 7090
[22]Langmuir,2017,vol. 33,p. 8076 - 8089
[23]New Journal of Chemistry,2019,vol. 43,p. 7950 - 7961
[24]European Journal of Medicinal Chemistry,2020,vol. 186

3
[ 30964-00-2 ]
[ 63478-76-2 ]

Yield	Reaction Conditions	Operation in experiment
		Preparation of hept-6-yn-l-olTo a round bottom flask equipped with a stirring bar under N2 was added LAH (3.61 g, 95 mmol) and anhydrous diethyl ether (300 ml). The mixture was cooled to 0 0C in an acetonitrile-dry ice bath, a solution of <strong>[30964-00-2]hept-6-ynoic acid</strong> (6.00 g, 47.6 mmol) in dry diethyl ether (60.1 ml) was added dropwise with vigorous stirring. The mixture was then allowed to warm to ambient temperature and stirred for an additional hour. Next, IM HCl solution (159 ml, 159 mmol) was added dropwise and the reaction mixture was stirred at ambient temperature over the weekend. The layers were then separated. The aqueous layer was back-extracted with diethyl ether (150 mL). The combined organic phase was wash with brine (15OmL), dried (MgSO4) and concentrated to yield 5.89 g of colorless liquid. The crude liquid was purified via Analogix FCC system using Biotage RS 330g column, with a gradient of 0-50% ether/pet, ether over 10 min. at 40 mL/min. then held at 50% for 50 min. Fractions containing product were combined and concentrated to yield hept-6-yn- l-ol (4.94 g, 44.0 mmol) as colorless liquid. The title compound was also prepared according to procedure described by B. W. Gung et al, Tetrahedron: Asymmetry, 2005, 16, 3107-3114. 1H NMR (400 MHz, DMSO-J6) delta ppm 3.66 (t, J = 6.32, 6.32 Hz, 2H), 2.26-2.17 (m, 2H), 1.98-1.92 (m, IH), 1.66-1.53 (m, 4H), 1.53-1.45 (m, 2H)

Reference： [1]Synlett,2001,p. 1221 - 1224
[2]Tetrahedron Asymmetry,2005,vol. 16,p. 3107 - 3114
[3]Organic Letters,2014,vol. 16,p. 1414 - 1417
[4]Chemistry of Natural Compounds,2011,vol. 46,p. 841 - 847
[5]Journal of Organic Chemistry,2004,vol. 69,p. 1126 - 1136
[6]Journal of the American Chemical Society,2005,vol. 127,p. 6686 - 6692
[7]Russian Journal of Bioorganic Chemistry,1998,vol. 24,p. 692 - 699
[8]Bulletin de la Societe Chimique de France,1984,vol. 2,p. 49 - 55
[9]Tetrahedron Letters,2008,vol. 49,p. 2899 - 2901
[10]Patent: WO2008/79382,2008,A1 .Location in patent: Page/Page column 126

4
[ 75-77-4 ]
[ 30964-00-2 ]
[ 473542-74-4 ]

Yield	Reaction Conditions	Operation in experiment
92%		A solution of <strong>[30964-00-2]hept-6-ynoic acid</strong> (1.90 g, 14.8 mmol) in anhydrous THF (90 mL) at -78 C was treated with H-BuLi (2.3 M in hexanes, 14.5 mL, 33.3 mmol). After stirring for 2 min, TMSCl (5.8 mL, 46.0 mmol) was added. The reaction mixture was allowed to warm slowly to 25 C and was stirred for 1 h. The reaction was quenched with the addition of aqueous 2 N HCl and extracted with CH2Cl2. The organic layer was dried over Na2SO4, filtered and concentrated. Column chromatography (SiO2, 4 x 6 cm, <n="35"/>20% EtOAc-hexanes) afforded 7-(trimethylsilyl)<strong>[30964-00-2]hept-6-ynoic acid</strong> (2.7 g, 13.6 mmol, 92%) as a white solid: 1H NMR (CDCl3, 500 MHz) delta 2.40 (t, 2H, J= 7.4 Hz), 2.24 (t, 2H, J = 7.3 Hz), 1.78-1.72 (m, 2H), 1.62-1.56 (m, 2H), 0.15 (s, 9H).

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 1849 - 1856
[2]Journal of Medicinal Chemistry,2007,vol. 50,p. 3359 - 3368
[3]Patent: WO2008/150492,2008,A1 .Location in patent: Page/Page column 33-34
[4]Journal of the Chemical Society. Perkin Transactions 1 (2001),2002,p. 1494 - 1514

5
[ 591-50-4 ]
[ 30964-00-2 ]
[ 49769-28-0 ]

Yield	Reaction Conditions	Operation in experiment
82%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; at 50℃; for 16h;Inert atmosphere;	To an oven dried flask were added Pd(PPh3)4 (173.3 nig, 0.15 mmol, 3 mol%) and Cul (19.0 mg, 0.1 mmol, 2 mol%) and the flask was flushed under N2 for 5 minutes, followed by addition of <strong>[30964-00-2]hept-6-ynoic acid</strong> (630.8 mg, 5 mmol, 1.0 equiv.), l-iodobenzene (1.22 g, 6 mmol, 1.2 equiv.) and triethylamine (20 mL). The reaction was heated to 50 C and stirred for i6h. Af- terwards the crude material was concentrated and Ethyl acetate (100 mL) and aq. HC1 (lM, 20 mL) were added and extracted. The water phase was extracted again with Ethyl acetate (100 mL) and the combined organic layers were drying over Na2S04 and concentrated. The crude material was purified by chromatography to afford 7-phenyl<strong>[30964-00-2]hept-6-ynoic acid</strong> (isolated yield 82 %) as brown solid. NMR (500 MHz, CDC13): delta 10.75 (br s, iotaEta), 7·43"7·36 (m, 2H), 7-32-7-22 (m, 3H), 2.45 (t, J = 7-1 Hz, 4H), 1.88-1.78 (m, 2H), 1.72-1.63 (m, 2H).

Reference： [1]Tetrahedron,2010,vol. 66,p. 1064 - 1069
[2]Patent: WO2015/144902,2015,A1 .Location in patent: Page/Page column 14
[3]Heterocycles,2003,vol. 59,p. 71 - 74
[4]Journal of Organic Chemistry,2006,vol. 71,p. 3612 - 3614

6
[ 30964-00-2 ]
[ 111-14-8 ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 93 - 102

7
[ 6066-82-6 ]
[ 30964-00-2 ]
[ 917222-23-2 ]

Yield	Reaction Conditions	Operation in experiment
72%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 18h;	<strong>[30964-00-2]6-heptynoic acid</strong> (5) (> 97%, TCI, Portland, OR) (1 g, 7.9 mmol, 1 equiv.) was dissolved in 100 ml of anhydrous methylene chloride. N-hydroxysuccinimide (NHS) (98+%, Acros, New Jersey) (2.3 g, 19.8 mmol, 2.5 equiv.) and l-(3-dimethylaminopropyl)- 3-ethylcarbodiimide hydrochloride (EDC) (98+%, Alfa Aesar) (2.3 g, 11.9 mmol, 1.5 equiv.) was added to the above solution. The resulting reaction mixture was stirred at room temperature overnight (18 hours) before 500 ml of a saturated sodium bicarbonate aqueous solution was added to it. The aqueous phase was extracted with 500 ml of ether. The ether extract was combined with the methylene chloride phase, washed with 500 ml of water and 500 ml of brine, and then dried with anhydrous magnesium sulfate. After magnesium <n="35"/>sulfate was filtered away and the solvent was removed by rotary evaporation, an off-white solid (1.3 g, 72 % yield) was obtained after being further dried overnight under vacuum. This solid was then used directly in the next step.

Reference： [1]Bioconjugate Chemistry,2016,vol. 27,p. 1624 - 1637
[2]Journal of the American Chemical Society,2006,vol. 128,p. 14468 - 14469
[3]Patent: WO2007/56389,2007,A2 .Location in patent: Page/Page column 32-33

8
[ 30964-00-2 ]
[ 16326-32-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: acid 2: 89 percent / K₂CO₃, NaI, CuI / dimethylformamide / 12 h 3: 92 percent / CBr₄, PPh₃ / CH₂Cl₂ / 1 h / Ambient temperature 4: 89 percent / K₂CO₃, NaI, CuI / dimethylformamide / 40 °C 5: 65 percent / H₂, (CH₂NH₂)2 / P-2 Ni / ethanol
	Multi-step reaction with 3 steps 1: ethyl magnesium bromide; tetrahydrofuran / anschliessend mit 1-Brom-undeca-2,5-diin und Kupfer(I)-cyanid 2: Lindlar-catalyst; quinoline; ethanol / Hydrogenation

Reference： [1]Durand, Sandrine; Parrain, Jean-Luc; Santelli, Maurice [Synthesis, 1998, # 7, p. 1015 - 1018]
[2]Osbond; Wickens [Chemistry and industry, 1959, p. 1288][Journal of the Chemical Society, 1961, p. 2779,2786] Osbond et al. [Journal of the Chemical Society, 1961, p. 2779,2783]

9
[ 30964-00-2 ]
[ 4617-33-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: diethyl ether 2: LiAlH₄ / diethyl ether / 2 h / 0 °C 3: 58 percent / LiNH₂, Fe(NO₃)3 / tetrahydrofuran; NH₃ / 20 h 4: H₂ / PtO₂ / diethyl ether

Reference： [1]Riche, Francoise; Mathieu, Jean-Paul; Vincens, Maurice; Bardy, Andre; Comet, Michel; Vidal, Michel [Bulletin de la Societe Chimique de France, 1984, vol. 2, # 1-2, p. 49 - 55]

10
[ 79496-61-0 ]
[ 30964-00-2 ]

Reference： [1]Journal of Organic Chemistry,1991,vol. 56,p. 1807 - 1812

11
[ 1119-46-6 ]
[ 30964-00-2 ]

Reference： [1]Journal of general chemistry of the USSR,1962,vol. 32,p. 57 - 62
Zhurnal Obshchei Khimii,1962,vol. 32,p. 58 - 64

12
[ 30964-00-2 ]
[ 100-46-9 ]
[ 623165-94-6 ]

Yield	Reaction Conditions	Operation in experiment
99%	With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In tetrahydrofuran; at 20℃; for 16h;	1- (3-dimethylaminopropyl)-3-ethylcarbodiimide (3.3 g, 17.4 mmol) was added to a mixture of <strong>[30964-00-2]6-heptynoic acid</strong> (1.1 g, 8.7 mmol), benzylamine (950 pi, 8.7 mmol), 1-hydroxybenzotriazole (1.2 g, 8.7 mmol) and triethylamine (2.4 ml, 17.4 mmol) in tetrahydrofuran (25 ml) and the mixture was stirred at room temperature for 16 hours. The reaction was diluted with sodium hydrogen carbonate (sat, 60 ml) and extracted with ethyl acetate (2 x 100 ml). The extracts were washed with brine, dried (MgS04) and evaporated in vacuo to a brown solid (2.1 g, 99%). (ES+) 216 ( (mol+).
99%	With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In tetrahydrofuran; at 20℃; for 16h;	1- (3-dimethylaminopropyl)-3-ethylcarbodiimide (3.3 g, 17.4 mmol) was added to a mixture of <strong>[30964-00-2]6-heptynoic acid</strong> (1.1 g, 8.7 mmol), benzylamine (950 fil, 8.7 mmol), 1-hydroxybenzotriazole (1.2 g, 8.7 mmol) and triethylamine (2.4 ml, 17.4 mmol) in tetrahydrofuran (25 ml) and the mixture was stirred at room temperature for 16 hours. The reaction was diluted with sodium hydrogen carbonate (sat, 60 ml) and extracted with ethyl acetate (2 x 100 ml). The extracts were washed with brine, dried (MgS04) and evaporated in vacuo to provide <strong>[30964-00-2]6-heptynoic acid</strong> N- benzylamide as a brown solid (2.1 g, 99%). (ES+) 216 ([MH] +).

Reference： [1]Patent: WO2003/93251,2003,A1 .Location in patent: Page/Page column 32
[2]Patent: WO2003/93253,2003,A1 .Location in patent: Page/Page column 21
[3]Organic Letters,2019,vol. 21,p. 3866 - 3870

13
[ 623577-65-1 ]
[ 30964-00-2 ]
C₂₃H₂₇F₃N₂O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
12%	With triethylamine;copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triphenylphosphine; In 1,4-dioxane; at 100℃; for 16h;	A mixture of Intermediate 1 (100 mg, 0.2 mmol), 6-heptynoic (101 pl, 0.8 mmol), tetrakis-triphenylphospine palladium (0) (12 mg, 5 mol%), triphenyl phosphine (5.2 mg, 10 mol%) and copper iodide (4 mg, 10 mol%) in triethylamine (2 ml) and dioxane (2 ml) was purged with nitrogen and then heated at 100oC for 16 hours. The reaction was diluted with hydrochloric acid (1N) and extracted with ethyl acetate (2 x 25 ml). The extracts were washed with water (x 3) and brine, dried (MgS04) and evaporated in vacuo to a yellow gum, which was purified by flash column chromatography on silica eluting with EtOAc: isohexane (1: 3) to give a foam which was further purified by preparative TLC eluting with EtOAc: isohexane (1: 3) to give a clear gum (11 mg, 12%). 8 (lH, 400 MHz, CDCIs) 1.25-1. 34 (2H, m), 1.57-1. 84 (6H, m), 2.32-2. 46 (8H, m), 2.55-2. 69 (2H, m), 3.18 (2H, dd, J = 16.0 & 9.7 Hz), 3.42 (2H, s), 3.67 (2H, q, J = 8.7 Hz), 7.00 (1 H, d, J = 8.2 Hz), and 7.14-7. 16 (2H, m). (ES+) 483 ([MH]-).

Reference： [1]Patent: WO2003/93253,2003,A1 .Location in patent: Page/Page column 24-25

14
[ 30964-00-2 ]
[ 14347-78-5 ]
[ 1146526-40-0 ]

Reference： [1]Angewandte Chemie - International Edition,2009,vol. 48,p. 1498 - 1500

15
N‐(6‐(diethylamino)‐9‐(2‐(piperazine‐1‐carbonyl)phenyl)‐3H-xanthen‐3‐ylidene)‐N‐ethylethanaminium chloride [ No CAS ]
[ 30964-00-2 ]
[ 1139651-78-7 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 4967 - 4975

16
[ 30964-00-2 ]
[ 183896-00-6 ]
[ 1139651-71-0 ]

Yield	Reaction Conditions	Operation in experiment
62%	Stage #1: hept-6-ynoic acid With 4-methyl-morpholine; isobutyl chloroformate In dichloromethane at 0℃; for 0.5h; Stage #2: N-(13-amino-4,7,10-trioxatridecanyl)-D-biotinamide In dichloromethane; N,N-dimethyl-formamide at 20℃; for 3h;

Reference： [1]Charron, Guillaume; Zhang, Mingzi M.; Yount, Jacob S.; Wilson, John; Raghavan, Anuradha S.; et al. [Journal of the American Chemical Society, 2009, vol. 131, p. 4967 - 4975]

17
[ 30964-00-2 ]
C₁₈H₂₅N₄O₇Pol [ No CAS ]
C₂₅H₃₅N₄O₉Pol [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 9195 - 9197

18
[ 30964-00-2 ]
C₃₃H₅₁N₈O₁₁Pol [ No CAS ]
C₄₀H₆₁N₈O₁₃Pol [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 9195 - 9197

19
[ 30964-00-2 ]
C₄₈H₇₇N₁₂O₁₅Pol [ No CAS ]
C₅₅H₈₇N₁₂O₁₇Pol [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 9195 - 9197

20
[ 844502-39-2 ]
[ 30964-00-2 ]
[ 109-89-7 ]
7-(5-cyano-4-hydroxy-6-oxo-3-phenyl-6,7-dihydrothieno[2,3-b]pyridin-2-yl)hept-6-ynoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of 2-Bromo-4-hydroxy-6-oxo-3-phenyl-6,7-dihydro-thieno[2,3-b]pyridine-5-carbonitrile (150 mg, 0.45 mmol) in 4.5 mL DMF was added diethylamine (0.48 mL, 4.5 mmol), followed by copper (I) iodide (trace), Pd(PPh3)Cl2 (10 mg, 0.015 mmol), and triphenylphosphine (36 mg, 0.12 mmol). The resulting mixture was stirred at rt for 5 min, after which <strong>[30964-00-2]hept-6-ynoic acid</strong> (0.19 mL, 1.5 mmol) was added. The reaction was then heated to 120 C. using microwave for 25 min, filtered, concentrated and purified by reverse phase HPLC. MS (ESI) m/e 393 (M+H)+; 1H NMR (400 MHz, DMSO-d6): delta ppm 1.28-1.56 (m, 4H), 2.12-2.30 (m, 4H), 7.20-7.35 (m, 5H).

Reference： [1]Patent: US2005/38068,2005,A1 .Location in patent: Page/Page column 67

21
3-(3-bromophenyl)-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile [ No CAS ]
[ 30964-00-2 ]
7-[3-(5-cyano-4-hydroxy-6-oxo-6,7-dihydrothieno[2,3-b]pyridin-3-yl)phenyl]hept-6-ynoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of 3-(3-bromo-phenyl)-4-hydroxy-6-oxo-6,7-dihydro-thieno[2,3-b]pyridine-5-carbonitrile (50 mg, 0.15 mmol) in 1.5 mL DMF was added diethylamine (0.16 mL, 1.5 mmol), followed by copper (I) iodide (trace), Pd(PPh3)Cl2 (3.5 mg, 0.005 mmol), and triphenylphosphine (12 mg, 0.04 mmol). The resulting mixture was stirred at rt for 5 min, after which <strong>[30964-00-2]hept-6-ynoic acid</strong> (63 muL, 0.5 mmol) was added. The reaction was then heated to 120 C. using microwave reactor for 25 min, filtered, concentrated and purified by reverse phase HPLC to give the titled compound. MS (ESI) m/e 391 (M-H)+; 1H NMR (300 MHz, DMSO-d6): delta 1.54 (m, 4H), 2.22 (m, 4H), 6.68 (s, 1H), 7.21-7.26 (m, 2H), 7.37-7.44 (m, 2H).

Reference： [1]Patent: US2005/38068,2005,A1 .Location in patent: Page/Page column 56

22
[ 30964-00-2 ]
[ 57493-24-0 ]
[ 1171848-11-5 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; trichlorophosphate at -13 - 20℃; for 0.5h;

Reference： [1]Location in patent: scheme or table Tapadar, Subhasish; He, Rong; Luchini, Doris N.; Billadeau, Daniel D.; Kozikowski, Alan P. [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 11, p. 3023 - 3026]

23
[ 30964-00-2 ]
[ 74-88-4 ]
[ 56909-02-5 ]

Yield	Reaction Conditions	Operation in experiment
75%		A solution of <strong>[30964-00-2]6-heptynoic acid</strong> (500muL, 3.95mmol) in acetone was treated with K2CO3 (273mg, 1.98mmol). The mixture was then stirred for 30min and MeI (2.5mL, 39mmol) was then added. The reaction mixture was stirred for 18h and then quenched with aq satd. NaHCO3 (5mL). The solution was washed with 10% aq Na2S2O3 (20mL), brine (20mL), and dried over Na2SO4. The solvent was then removed under vacuum to give 406mg (75%) of the desired methyl ester 13 as a colourless oil. 1H NMR (CDCl3, 500MHz) delta: 3.69 (3H, s), 2.36 (2H, t, J=7.3Hz), 2.23 (2H, td, J=7.0, 2.6Hz), 1.95 (1H, t, J=2.7Hz), 1.81-1.75 (2H, m), 1.62-1.56 (2H, m). 13C NMR (CDCl3, 125MHz) delta: 174.1, 83.8, 68.6, 51.4, 33.4, 27.9, 23.9, 18.0.

Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 5585 - 5587
[2]Tetrahedron,2013,vol. 69,p. 8527 - 8533
[3]Journal of the American Chemical Society,2018,vol. 140,p. 7385 - 7389

24
[ 1008854-95-2 ]
[ 30964-00-2 ]
[ 1008854-96-3 ]

Yield	Reaction Conditions	Operation in experiment
56.57%		To a stirred solution of <strong>[30964-00-2]6-heptynoic acid</strong> (0.3022 g, 2.40 mmol) in anhydrousTHF (50 mL) were added DCC (0.4952 g, 2.40 mmol) and HOBt (0.3245 g, 2.40 mmol) at room temperature. The mixture was stirred for 2 h, then dendrimer Bl 4 (1.0432 g, 0.48 mmol) was added and the resulting solution was stirred for 40 h. After filtration and removal of THF, the product was purified by flash column chromatography, eluting with ethyl acetate/methanol gradient to yield Bl 5 (0.620 g, 56.57%). 1H NMR (400 MHz, CD3OD): delta = 1.53 (m, CH2, 2 eta), 1.71 (m, CH2, 3 eta), 1.890-2.5 (m, CH2, 50 eta), 3.30 (m, CH2, 36 H); 13C NMR (400 MHz, CD3OD): delta-18.81, 26.14, 29.43, 31.27, 31.80, 37.37, 39.35, 40.43, 58.83, 59.05, 69.95, 83.4, 111.74, 115.57, 119.37, 123.13, 158.55, 159.07, 159.53, 159.99, 175.60, 176.25.

Reference： [1]Patent: WO2008/24435,2008,A2 .Location in patent: Page/Page column 92

25
[ 30964-00-2 ]
[ 1309806-53-8 ]
[ 1309806-56-1 ]

Yield	Reaction Conditions	Operation in experiment
45%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; N,N-dimethyl-formamide; at 20℃; for 16h;Inert atmosphere;	Diamine 7 (3 mg, 6.3 mumol) was dried azeotropically with anhydrous toulene (2 × 2 mL) then dissolved in anhydrous CH2Cl2 and DMF (1 mL, 1:1, v/v). N-(3-Dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (EDC×HCl, 2.5 mg, 12.6 mumol) and <strong>[30964-00-2]6-heptynoic acid</strong> (1.6 muL, 12.6 mumol) were added to this solution. After stirring at rt for 16 h, the reaction mixture was diluted with CH2Cl2 (10 mL) and washed with H2O (3 × 5 mL). The organic phase was evaporated to dryness, and the resulting crude residue was purified by silica gel column chromatography (0-7% MeOH in CH2Cl2, v/v) to afford terminal alkyne 11 as a white solid (1.62 mg, 45%). ESI-HRMS m/z 584.2744 [M + H]+, C30H34N9O4?H+: Calcd. 584.2734; 1H NMR (CDCl3) d 8.20 (s, 1H), 7.65 (d, J = 1.2 Hz, 1H), 7.27 (s, 1H), 7.12-7.17 (d, 2H, J = 8.6 Hz), 6.82-6.86 (d, 2H, J = 8.6 Hz), 6.61-6.64 (m, 1H), 6.07 (s, 2H), 4.47 (s, 2H), 4.37 (t, 2H, J = 7.0 Hz), 3.36-3.52 (m, 4H), 2.64 (t, 2H, J = 7.4 Hz), 2.17-2.30 (m, 3H), 1.67-1.78 (m, 4H), 1.21-1.34 (m, 2H), 0.89 (t, 2H, J = 6.2 Hz).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 2740 - 2745

26
[ 30964-00-2 ]
[ 3128-07-2 ]

Yield	Reaction Conditions	Operation in experiment
88%	With [RhCl2(p-cymene)]2; water; at 20℃; for 12h;	General procedure: To a solution of alkyne (1.0 mmol) in PEG-400/H2O(4:1) was added [Ru(p-cymene)Cl2]2 (0.01 mmol), and themixture stirred at room temperature. Upon completion of thereaction (monitoring by TLC), the reaction mixture was dilutedwith Et2O (10 mL), stirred for 10 min, and allowed to stand in anice-salt bath to solidify the PEG-400. The organic layer wasdecanted, dried over anhydrous Na2SO4, filtered, and concentratedunder reduced pressure. The residue obtained was purifiedby silica gel flash column chromatography (ethyl acetate-petroleum ether) to give the pure product.

Reference： [1]Synlett,2016,vol. 27,p. 1969 - 1972
[2]Dalton Transactions,2010,vol. 39,p. 10601 - 10607

27
[ 30964-00-2 ]
[ 1956-30-5 ]
[ 1311414-16-0 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 4847 - 4862

28
2-(2'-hydroxyethylamino)-4,6-di(4'-methoxybenzylamino)-1,3,5-triazine [ No CAS ]
[ 30964-00-2 ]
[ 1391054-32-2 ]

Yield	Reaction Conditions	Operation in experiment
92%	With dmap; dicyclohexyl-carbodiimide; In tetrahydrofuran; at 20℃; for 24h;Inert atmosphere;	General procedure: A solution of 7 (1 g, 2.4 mmol), 4-pentinoic acid (0.27 g, 2.6 mmol), DCC (0.7 g, 3.1 mmol) and DMAP (0.37 g, 3 mmol) in THF (4 ml) was stirred for 24 h at room temperature under nitrogen atmosphere. The solvent was removed and the residue was purified by flash chromatography on silica gel (EtOAc/pentane, 1:1, then EtOAc) to give 2,4-di(4'-methoxybenzylamino)-6-[2'-(4-pentynoyloxy)ethylamino]-1,3,5-triazine 9a (1.12 g, 2.3 mmol, 96%) as a white oil.

Reference： [1]Bioorganic and Medicinal Chemistry,2012,vol. 20,p. 4271 - 4278

29
[ 30964-00-2 ]
[ 16357-59-8 ]
[ 92640-91-0 ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 12529 - 12533
Angew. Chem.,2012,vol. 124,p. 12697 - 12701,5

30
[ 30964-00-2 ]
(1R,2S,3S,4R,5R,6R)-5-(hydroxymethyl)-7-azabicyclo[4.1.0]heptane-2,3,4-triol [ No CAS ]
[ 1334306-90-9 ]

Yield	Reaction Conditions	Operation in experiment
52%	With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; In N,N-dimethyl-formamide;	1-((1R,2S,3S,4R,5R,6R)-2,3,4-trihydroxy-5-(hydroxymethyl)-7-azabicyclo[4.1.0]heptan-7-yl)hept-6-yn-1-one [0245] [0246] Aziridine xxx (10 mg, 57 mmol) was dissolved in DMF (1 mL). A solution of EEDQ ( . . . muL, 250 mmol) and <strong>[30964-00-2]hept-7-ynoic acid</strong> ( . . . muL, 250 mumol) in DMF (250 muL) was added. After overnight stirring, TLC-analysis showed incomplete conversion and an additional amount of EEDQ and <strong>[30964-00-2]hept-7-ynoic acid</strong> was added. After 1 h, the reaction was concentrated under reduced pressure. Silica gel column chromatography (CH2Cl2 10% MeOH/CH2Cl2) afforded acetylated aziridine xxx (52%, 8.42 mg, 30 mmol). 1H NMR (400 MHz, MeOD) delta 4.09 (dd, J=10.3, 4.4 Hz, 1H), 3.71 (dd, J=13.5, 5.7 Hz, 2H), 3.37 (s, 1H), 3.23 (dd, J=10.0, 8.1 Hz, 1H), 3.10 (t, J=9.9 Hz, 1H), 3.06 (dd, J=5.8, 2.9 Hz, 1H), 2.76 (d, J=5.8 Hz, 1H 2.55 (td, J=7.2, 1.7 Hz, 2H), 2.26-2.17 (m, 3H), 2.06-1.95 (m, 1H), 1.81-1.70 (m, 2H), 1.63-1.51 (m, 2H). 13C NMR (101 MHz, MeOD) delta 77.67, 71.98, 68.37, 67.92, 62.13, 43.85, 41.06, 39.69, 34.94, 27.75, 23.75, 17.40.

Reference： [1]Patent: US2013/143228,2013,A1 .Location in patent: Paragraph 0245; 0246
[2]European Journal of Organic Chemistry,2014,vol. 2014,p. 6030 - 6043

31
[ 30964-00-2 ]
[ 1384432-87-4 ]
[ 1415600-27-9 ]

Yield	Reaction Conditions	Operation in experiment
85%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 60℃; for 15h;Inert atmosphere;	1.12 g (1.20 mmol) of compound 11, 182 mg (1.44 mmol) of <strong>[30964-00-2]6-heptynoic acid</strong> at 90% and 42 (0.06 mmol) mg of [Pd(PPh3)2Cl2], all in solution in 80 mL of freshly distilled THF and 24 mL of triethylamine are introduced into a 250-mL two-necked flask. The solution is degassed by passing through a continuous stream of nitrogen for 30 min 22.9 mg (0.1 mmol) of CuI is added and then the reaction mixture is heated at 60 C. for 15 hours. The solvent is removed by evaporation and successive co-evaporations with dichloromethane. The oily residue is taken up in 250 mL of a CH2Cl2/H2O mixture (50/50), and then the aqueous phase is extracted. The organic phase is washed with saturated NaCl solution, and then dried over Na2SO4. The residue is purified by silica gel column chromatography. The eluent used is a CH2Cl2/MeOH mixture (100/0 to 93/7). 1.01 g (1.02 mmol) of compound 12 is obtained in the form of a brown oil, i.e. a yield of 85%. Compound 12 has the following characteristics: Rf=0.27; SiO2; CH2Cl2/MeOH (90/10). 1H NMR (CDCl3, 300 MHz): delta 1.33 (t, J=7.0 Hz, 24H); 1.70 (m, 2H); 1.95 (m, 2H); 2.43 (m, 2H); 2.51 (m, 2H); 3.26 (d, J=10 Hz, 8H); 4.05-4.35 (m, 20H); 6.50 (d, J=2.6 Hz, 2H); 7.82 (s, 2H); 8.45 (d, J=2.6 Hz, 2H). 13C NMR (CDCl3, 75 MHz): delta 16.5 (d, J=6.1 Hz); 19.1; 19.4; 24.0; 27.2; 50.1 (dd, J=159.9 Hz, J=9.4 Hz); 58.3; 62.2 (d, J=7.0 Hz); 96.6; 108.8; 111.4; 127.67; 137.4; 150.0; 152.1; 175.4; 206.9. 31P NMR (CDCl3, 161.9 MHz): delta 24.73. [0378] Analyses calculated for C40H67N7O14P4: C, 48.34; H, 6.79; N, 9.86. Found: C, 48.52; H, 7.12; N, 9.65. IR (cm-1, ATR): nu 2233, 1720, 1211, 1019, 987, 795. EI+/MS: m/z 994.4 ([12+H]+, 100%).

Reference： [1]Organic and Biomolecular Chemistry,2013,vol. 11,p. 6493 - 6501
[2]Physical Chemistry Chemical Physics,2014,vol. 16,p. 6060 - 6067
[3]Patent: US2014/199243,2014,A1 .Location in patent: Paragraph 0364; 0373-0380

32
[ 30964-00-2 ]
[ 1449305-69-4 ]
[ 1449305-70-7 ]

Yield	Reaction Conditions	Operation in experiment
99%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; at 55℃; for 30h;Inert atmosphere;	A mixture of 7-iodo-1-methyl-5-phenyl-2,3-dihydro-1H-1,4-benzodiazepin-2-one 13 [7] (1.01 g, 2.68 mmol), <strong>[30964-00-2]6-heptynoic acid</strong> (0.51 mL, 4.02 mmol), CuI (0.06 g, 0.32 mmol), Pd(PPh3)4 (0.12 g,0.11 mmol) and anhydrous Et3N (15 mL) were heated at 55 C for30 h under nitrogen, then it was partitioned between a saturatedsolution of NH4Cl and ethyl acetate. The organic layer was collectedand the solvent was removed under vacuum, then the residue wastreated with HCl 2 N (30 mL) and washed with EtOAc (3 30 mL),then added with NaHCO3 until pH 7 and extracted with EtOAc. Drying (Na2SO4) of the second organic phase and removal of thesolvent gave the title compound in 80% yield. Yellow solid, m.p. 51e52 C. [1H] NMR (CDCl3) d: 1.59e1.66 (m, 2H, CH2); 1.72e1.80 (m,2H, CH2); 2.36e2.44 (m, 4H, 2CH2); 3.41 (s, 3H, NCH3); 3.78 (d,J 11.4 Hz, 1H, CHH); 4.86 (d, J 11.4 Hz, 1H, CHH); 7.29 (d,J 8.8 Hz, 1H, arom.); 7.33 (d, J 2.0 Hz, 1H, arom.); 7.42e7.46 (m,2H, arom.); 7.50e7.53 (m,1H, arom.); 7.59 (dd, J 8.8 Hz, 2.0 Hz, 1H,arom.); 7.63e7.67 (m, 2H, arom.) ppm.

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 66,p. 56 - 68

33
[ 30964-00-2 ]
[ 3772-55-2 ]
C₂₇H₃₈O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20℃;	General procedure: Esterification of DHA and dehydroabietinol was performed using DCC/DMAP and appropriate alcohol (propargyl alcohol or 3-butyn-1-ol) or acid (4-pentynoic acid or <strong>[30964-00-2]6-heptynoic acid</strong>) according to reference [18]. Briefly, DHA or alkynyl acid (1 eq) was dissolved in dry CH2Cl2 at room temperature under constant stirring. Then, DCC (1 eq) was added, followed by a catalytic amount of DMAP and alkynyl alcohol or dehydroabietinol (1 eq) dissolved in dry CH2Cl2. The reaction was stopped by adding H2O, extracted with CH2Cl2, dried over Na2SO4, concentrated and purified (60%-81% yield).

Reference： [1]Molecules,2014,vol. 19,p. 2523 - 2535
[2]Molecules,2017,vol. 22

34
[ 30964-00-2 ]
[ 70978-37-9 ]
[ 598-54-9 ]
[ 298-06-6 ]
[ 146-75-8 ]
[ 1613513-20-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium chloride; In water; ethyl acetate; tert-butyl alcohol;	Step 2: 5-(1-(4-Methoxybenzyl)-1H-1,2,3-triazol-4-yl)pentanoic acid 1-(Azidomethyl)-4-methoxybenzene (259 mg, 1.585 mmol) was solubilised in t-BuOH (15.9 ml). Hept-6-ynoic acid (201 mul, 1.585 mmol) was added followed by water (15.9 ml) copper acetate (28.2 mg, 0.159 mmol) and sodium L-ascorbate (63 mg, 0.317 mmol). The reaction mixture was stirred at RT for 72 hrs. Sodium chloride was added and the mixture was stirred vigorously. EtOAc was added and the phases were separated. The aqueous layer was re-extracted with EtOAc and the combined organics were treated with charcoal & MgSO4 (anh), stirring for 5 minutes. The resulting mixture was filtered and the filtrate was evaporated under reduced pressure to afford the title compound; LCMS: Rt 0.87 mins MS m/z 290.3 [M+H]+Method 2minLowpHv01

Reference： [1]Patent: US2014/171403,2014,A1 .Location in patent: Page/Page column

35
[ 30964-00-2 ]
[ 68061-76-7 ]
3-(hept-6-ynoyl)-4-hydroxy-5,6,7-trimethoxy-2H-chromen-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 0 - 35℃;Schlenk technique; Inert atmosphere;	General procedure: 4-hydroxycoumarin (1 equiv) and DMAP (0.5 equiv) were dissolved in DMF (3 mL) at 0C. Acid (1.5 equiv) and EDC·HCl (1.5equiv) were dissolved in DMF (3 mL) in a Schlenk flask under argon.The mixture was stirred at 0C (30 min) and added via syringe to the flask containing 4-hydroxycoumarin and DMAP. The mixture was stirred at 0C (1 h) and then at 35C until complete coumarin consumption (TLC). The solvent was removed under reduced pressure at 50C and the residue was dissolved in water and extracted with CH2Cl2. The combined organic phases were washed with 0.05 M NaOH, and the solvent was removed under reduced pressure. The product was purified by column chromatography (EtOAc-petroleum ether) to give products 6-12 and 14.

Reference： [1]Synthesis,2014,vol. 46,p. 3239 - 3248

36
[ 30964-00-2 ]
[ 213481-01-7 ]
10-(hept-6-ynoyl)-9-hydroxy-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinolin-11-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 0 - 35℃;Schlenk technique; Inert atmosphere;	General procedure: 4-hydroxycoumarin (1 equiv) and DMAP (0.5 equiv) were dissolved in DMF (3 mL) at 0C. Acid (1.5 equiv) and EDC·HCl (1.5equiv) were dissolved in DMF (3 mL) in a Schlenk flask under argon.The mixture was stirred at 0C (30 min) and added via syringe to the flask containing 4-hydroxycoumarin and DMAP. The mixture was stirred at 0C (1 h) and then at 35C until complete coumarin consumption (TLC). The solvent was removed under reduced pressure at 50C and the residue was dissolved in water and extracted with CH2Cl2. The combined organic phases were washed with 0.05 M NaOH, and the solvent was removed under reduced pressure. The product was purified by column chromatography (EtOAc-petroleum ether) to give products 6-12 and 14.

Reference： [1]Synthesis,2014,vol. 46,p. 3239 - 3248

37
[ 30964-00-2 ]
[ 153086-78-3 ]
tert-butyl (2-(2-(2-(hept-6-ynamido)ethoxy)ethoxy)ethyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82.9%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In acetonitrile; at 18℃;	Synthesis of 2 (Scheme B) The amine (1) (2g, MeCN solution) was coupled to 1 molar equivalent of <strong>[30964-00-2]hept-6-ynoic acid</strong> using EDCI.HC1 by stirring over weekend at 18 C. The raw material was in vacuo evaporated at 40 C, dissolved in EtOAc, washed in sequence with water, HC1 0.5 mM, water and sat. NaHC03. The organic part was dried on MgS04 to yield the desired amide (2, 2.38g, 82.9%) as a clear colorless oil. 1H-NMR spectrum in CDC13 is in accordance with the structure of compound 2.
76%	With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; at 20℃; for 22h;Cooling with ice;	To an ice-cooled solution of compound 1440 (2.2g, 8.72mmol), <strong>[30964-00-2]6-heptynoic acid</strong> (1.0g, 7.93mmol), HOBt (535.4mg, 3.96mmol) and TEA (8.9mL, 63.44mmol) in DMF (60mL) was slowly added a solution of DCC (2.0g, 9.51mmol) in DMF (20mL). The reaction mixture was stirred at rt for 22h. It was then concentrated to dryness under vacuum. The residue was dissolved in CH2Cl2 (200mL), and the solution was washed with 5% citric acid (50mL, ×3), 5% NaHCO3 (50mL, ×3), H2O (50mL, ×2), and brine (50mL, ×2). The organic phase was dried over anhydrous Na2SO4, filtered and concentrated. Purification by silica gel column chromatography (eluent: 100-90% CHCl3/MeOH) provided the desired product 15 (2.4g, 76%) as a pale yellow oil. Rf=0.44 (CHCl3/MeOH=9/1). 1H NMR (400MHz, CDCl3): delta 6.44 (br, 1H, NH), 5.12 (br, 1H, NH), 3.52-3.34 (m, 8H), 3.25 (q, J=5.4Hz, 2H), 3.12 (d, J=4.9Hz, 2H), 2.08-1.96 (m, 4H), 1.81 (t, J=2.5Hz, 1H), 1.62-1.50 (m, 2H), 1.44-1.30 (m, 2H), 1.26 (s, 9H); 13C NMR (100MHz, CDCl3): delta 172.6 (C), 155.7 (C), 83.7 (C), 78.8 (C), 69.8 (CH2), 69.8 (CH2), 69.8 (CH2), 69.5 (CH2), 68.4 (CH), 39.9 (CH2), 38.8 (CH2), 35.4 (CH2), 28.0 (CH3), 27.6 (CH2), 24.4 (CH2), 17.8 (CH2). IR (neat): 3301, 3083, 2933, 2869, 2116, 1695, 1651, 1455, 1392, 1366, 1279, 1251, 1171, 863, 638cm-1. ESI-MS calcd for C18H33N2O5 (M+H)+ 357.2389, found 357.2390.

Reference： [1]Patent: WO2017/13547,2017,A1 .Location in patent: Page/Page column 63-64
[2]Tetrahedron,2016,vol. 72,p. 58 - 68

38
[ 30964-00-2 ]
(4aR)-1-[(2,3-difluoro-4-iodophenyl)methyl]-4-hydroxy-4a-methyl-2-oxo-6,7-dihydro-5H-pyrrolo[1,2-b]pyridazine-3-carboxylic acid 2-methylpropyl ester [ No CAS ]
7-[4-[[(4aR)-4-hydroxy-4a-methyl-3-(2-methylpropoxycarbonyl)-2-oxo-6,7-dihydro-5H-pyrrolo[1,2-b]pyridazin-1-yl]methyl]-2,3-difluorophenyl]hept-6-ynoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 20℃; for 2.5h;Inert atmosphere;	Reference Example 72 7-[4-[[(4aR)-4-Hydroxy-4a-methyl-3-(2-methylpropoxycarbonyl)-2-oxo-6,7-dihydro-5H-pyrrolo[1,2-b]pyridazin-1-yl]methyl]-2,3-difluorophenyl]hept-6-ynoate A suspension of (4aR)-1-[(2,3-difluoro-4-iodophenyl)methyl]-4-hydroxy-4a-methyl-2-oxo-6,7-dihydro-5H-pyrrolo[1,2-b]pyridazine-3-carboxylic acid 2-methylpropyl ester (Reference Example 5) (250 mg, 0.480 mmol), <strong>[30964-00-2]hept-6-ynoic acid</strong> (0.182 mL, 1.44 mmol), copper (I) iodide (18.3 mg, 0.0960 mmol), triethylamine (0.335 mL, 2.40 mmol), and bis(triphenylphosphine)palladium (II) chloride (33.7 mg, 0.0480 mmol) in tetrahydrofuran (0.961 mL) was stirred under nitrogen atmosphere at room temperature for 2.5 hours. At the same time, the completely same reaction was run in another vessel on the same scale, and both resultants were combined and purified by C18 reverse-phase column chromatography to obtain the title compound (328 mg, 66%) as yellow oil. LCMS: m/z 519[M+H]+ HPLC retention time: 1.00 minute (analysis condition SQD-FA05)

Reference： [1]Patent: US2016/2251,2016,A1 .Location in patent: Paragraph 1522-1524

39
[ 30964-00-2 ]
[ 30963-94-1 ]

Yield	Reaction Conditions	Operation in experiment
	With iodine; potassium hydroxide; In methanol; water; at 23℃; for 72h;Inert atmosphere; Cooling with ice; Darkness;	Potassium hydroxide (85%, 32 g, 0.49 mol) was dissolved in a stirred solution of <strong>[30964-00-2]6-heptynoic acid</strong> (18 g, 0.14 mol) in 145 mL of MeOH and 72 mL of H2O under N2. The solution was cooled in ice. Iodine (44 g, 0.17 mol) was added and the flask was wrapped with Al foil to exclude light. The temperature was allowed to rise to 23 C over several hours. After 3 days the colorless mixture was poured into excess 1 M aq NaHSO4 where upon excess I2 was liberated. The product was extracted into EtOAc and the brown color of I2 was discharged with NaHSO3. The organic solution was extracted with water (2×) and brine, dried (MgSO4), filtered and concentrated to give 37.4 g of 2 as a tan solid. This material was used in the following step without purification.

Reference： [1]Prostaglandins and other lipid mediators,2016,vol. 123,p. 33 - 39

40
C₁₅H₁₈O₄ [ No CAS ]
[ 30964-00-2 ]

Yield	Reaction Conditions	Operation in experiment
96%	With iron(III) chloride; In dichloromethane; at 20℃; for 0.0833333h;Inert atmosphere; Green chemistry;	General procedure: To a solution of the 2,4-DMPM ester (0.2 mmol) in CH2Cl2 (1 mL) was added FeCl3(0.01 mmol), then stirred at room temperature under argon. After being stirred until the reaction was completed, the reaction mixture was directly filtrated through a small amount of a silica-gel pad and washed with Et2O. The filtrate was concentrated in vacuoto give the sufficiently-pure carboxylic acid. When some peaks derived from undetermined side-products were observed in the 1H-NMR spectra, the analytically-pure deprotected carboxylic acid was obtained after the normal silica-gel column chromatography (Table 3).

Reference： [1]Chemical and Pharmaceutical Bulletin,2016,vol. 64,p. 778 - 784

41
[ 30964-00-2 ]
[ 15992-83-3 ]
(E)-7-(4-((2,6-difluoro-4-(6-(3-(pyridin-2-yl)ureido)hex-1-yn-1-yl)phenyl)diazenyl)-3,5-difluorophenyl)-N-(1,8-naphthyridin-2-yl)hept-6-ynamide [ No CAS ]
(Z)-7-(4-((2,6-difluoro-4-(6-(3-(pyridin-2-yl)ureido)hex-1-yn-1-yl)phenyl)diazenyl)-3,5-difluorophenyl)-N-(1,8-naphthyridin-2-yl)hept-6-ynamide [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 3349 - 3353
Angew. Chem.,2017,vol. 129,p. 3397 - 3401,5

42
[ 30964-00-2 ]
[ 15992-83-3 ]
N-(1,8-naphthyridin-2-yl)hept-6-ynamide [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 3349 - 3353
Angew. Chem.,2017,vol. 129,p. 3397 - 3401,5

43
[ 63478-76-2 ]
[ 30964-00-2 ]

Yield	Reaction Conditions	Operation in experiment
88%	With Jones reagent; In acetone; at 0℃;	Compound 14 (3.00 g, 26.7 mmol) in 50 mL of acetone, the Jones reagent 7 was added dropwise at 0 C until the color of the mixture became dark green to orange. Then, 2-propanol was added dropwise until the color of the mixture returned to dark green. The mixture was poured into 100 mL of water, and it was extracted with chloroform. The combined organic layer was dried over anhydrous sodium sulfate. After filtration, solvent in the filtrate was removed under reduced pressure to give 2.95 g (88 %) of 15 as colorless liquid

Reference： [1]Bulletin of the Chemical Society of Japan,2017,vol. 90,p. 298 - 305

44
[ 30964-00-2 ]
[ 151237-05-7 ]
N-(3,4,5-tri(dodecyloxy)phenyl)-6-heptynamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%		To 21 (0.156 g, 1.24 mmol) in dichloromethane (20 mL), DCC (0.359 g, 1.74 mmol) and 1-hydroxybenzotriazole (HOBt) (0.235 g, 1.74 mmol) were added, and the mixture was stirred at 0 C for 1 h under a nitrogen atmosphere. Then, 15 (0.800 g, 1.24 mmol) and triethylamine (0.125g, 1.24 mmol) was added, and stirring was further continued at ambient temperature overnight. After filtration of the resulting mixture, the filtrate was washed with saturated sodium hydrogen carbonate solution three times. The organic layer was dried over anhydrous sodium sulfate. After filtration, solvent of the filtrate was evaporated under reduced pressure, and the residue was purified by column chromatography (silica gel, chloroformethyl acetate (9:1)). The fractionated portion was recrystallized from chloroform-methanol mixture to give 0.640 g (69 %) of 22 as white solid

Reference： [1]Bulletin of the Chemical Society of Japan,2017,vol. 90,p. 298 - 305

45
[ 52064-97-8 ]
[ 30964-00-2 ]
C₂₂H₁₇N₂O₅Re [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With silver trifluoromethanesulfonate; trimethylamine; In tetrahydrofuran; at 70℃; for 72h;Inert atmosphere; Schlenk technique;	General procedure: General procedure for the synthesis of fac-[Re(CO)3(1,10-phenantroline)L] L = heptanoic acid,<strong>[30964-00-2]hept-6-ynoic acid</strong> and 4-(1-ferrocenyl)-butanoic acid 1, 2, 3 complexes:Trimethylamine (46 mg, 0.045 mmol, 63 L) and silver trifluoromethanesulfonate (116 mg,0.45 mmol) were added to a stirred mixture of the acid (0.3 mmol) and fac-[Re(CO)3(1,10-phenantroline)Cl] (220 mg, 0.45 mmol) in THF (60 mL). The reaction mixture was stirred underargon atmosphere at 70 C for 18 h (for 1 and 3) or 72 h (for 2). The solvent was evaporated to dryness to afford a solid which was subjected to column chromatography on deactivated Al2O3 (Al2O3/H2O30 g: 1.25 g) with dichloromethane as eluent. Crystallization from dichloromethane/n-hexane gavepure products.

Reference： [1]Molecules,2017,vol. 22

46
[ 30964-00-2 ]
[ 76186-04-4 ]
(S)-N-(6-heptynoyl)-4-isopropyl-1,3-thiazolidine-2-thione [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 6426 - 6433

47
[ 30964-00-2 ]
[ 76186-04-4 ]
(S)-N-[(R)-2-(2,4,6-cycloheptatrien-1-yl)-6-heptynoyl]-4-isopropyl-1,3-thiazolidine-2-thione [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 6426 - 6433

48
[ 30964-00-2 ]
6-azidohept-6-enoic acid [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2020,vol. 142,p. 7083 - 7091
[2]Organic Letters,2017,vol. 19,p. 6240 - 6243

49
[ 1287-13-4 ]
[ 30964-00-2 ]
(6-heptyn-1-oyl)ruthenocene [ No CAS ]

Reference： [1]Dalton Transactions,2017,vol. 46,p. 17041 - 17052

50
[ 30964-00-2 ]
[ 39657-45-9 ]
1-(2-isoxazolidinyl)-6-heptyn-1-one [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 16342 - 16346
Angew. Chem.,2017,vol. 129,p. 16560 - 16564,5

51
[ 30964-00-2 ]
C₇₇H₁₀₈F₂₇N₂₁O₂₁ [ No CAS ]
C₈₄H₁₁₆F₂₇N₂₁O₂₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56.57%		To a stirred solution of <strong>[30964-00-2]6-heptynoic acid</strong> (0.3022 g, 2.40 mmol) in anhydrous THF (50 mL) were added DCC (0.4952 g, 2.40 mmol) and HOBt (0.3245 g, 2.40 mmol) at room temperature. The mixture was stirred for 2 h, then dendrimer B14 (1.0432 g, 0.48 mmol) was added and the resulting solution was stirred for 40 h. After filtration and removal of THF, the product was purified by flash column chromatography, eluting with ethyl acetate/methanol gradient to yield B15 (0.620 g, 56.57%). 1H NMR (400 MHz, CD3OD): delta=1.53 (m, CH2, 2 H), 1.71 (m, CH2, 3 H), 1.890-2.5 (m, CH2, 50 H), 3.30 (m, CH2, 36 H); 13C NMR (400 MHz, CD3OD): delta?=?18.81, 26.14, 29.43, 31.27, 31.80, 37.37, 39.35, 40.43, 58.83, 59.05, 69.95, 83.4, 111.74, 115.57, 119.37, 123.13, 158.55, 159.07, 159.53, 159.99, 175.60, 176.25.

Reference： [1]Patent: US9856348,2018,B2 .Location in patent: Page/Page column 134

52
[ 884535-05-1 ]
[ 30964-00-2 ]
1-(4,4-bis(hydroxymethyl)piperidin-1-yl)hept-6-yn-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92.4%		A solution of 7-heptynoic acid (Chem Impex International, Inc., 1.26 g, 10 mmol), N-hydroxybenzotriazole (HOBt, 1.837 g, 12 mmol) and EDC-HCl (2.300 g, 12 mmol) in DCM (40 mL) was stirred at room temperature for 30 min. Compound 3 (2.276 g, 12.53 mmol) and DIPEA (3.102 g, 24 mmol) were added at 0 C. The reaction mixture was stirred for 18 h at room temperature, washed with 5% NaHCO3, 5% HCl, brine. The extract was dried over Na2SO4 and evaporated. The crude product was purified on a silica gel column (2% AcOH, 2-10% MeOH, DCM), to give 2.341 g (92.4%) of diol 5d as a white solid.

Reference： [1]Patent: US2018/16232,2018,A1 .Location in patent: Paragraph 0175-0176

53
[ 30964-00-2 ]
6-amino-1-(3-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3-(hydroxymethyl)azetidin-1-yl)hexan-1-one [ No CAS ]
N-(6-(3-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3-(hydroxymethyl)azetidin-1-yl)-6-oxohexyl)hept-6-ynamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63.7%		Hept-6-ynoic acid (TCI America, 0.242 g, 1.92 mmol), HOBt (0.294 g, 1.92 mmol) and EDC-HCl (0.368 g, 2.304 mmol) were dissolved in DCM (5 mL) and stirred at room temperature for 30 min. This mixture was added to the solution of compound 25 (1.208 g, 1.60 mmol) and DIPEA (0.496 g, 3.84 mmol) in DCM (15 mL) at 0 C. The reaction mixture was stirred for 18 h at room temperature and was diluted with DCM (50 mL). The obtained solution was washed with 5% NaHCO3 and brine and was dried over Na2SO4. The extract was evaporated, and the residue was separated on a silica gel column (1-5% MeOH, DCM) to give 0.653 g (63.7%) compound 29b as a white solid foam. NMR H1 (delta, CDCl3): 7.37-7.39 (m, 2H), 7.25-7.29 (m, 6H), 7.18-7.20 (m, 1H), 6.79-6.83 (m, 4H), 5.99 (br. t, J=5.5 Hz, 1H), 3.94 (d, J=8.5 Hz, 1H), 3.66-3.80 (m, 11H), 3.27, 3.31 (AB, J=9.5 Hz, 2H), 3.17-3.23 (m, 2H), 2.13-2.20 (m, 4H), 2.01-2.07 (m, 2H), 1.92 (t, J=3.0 Hz, 1H), 1.70-1.74 (m, 2H), 1.45-1.56 (m, 6H), 1.30-1.35 (m, 2H). NMR C13 (delta, CDCl3): 173.6, 173.0, 158.8, 144.7, 135.8, 130.4, 128.2, 128.1, 127.1, 113.4, 86.4, 84.3, 68.8, 65.6, 65.4, 55.4, 54.8, 53.6, 39.3, 39.3, 36.2, 31.2, 29.4, 28.1, 26.6, 25.0, 24.4, 18.3.

Reference： [1]Patent: US2018/16232,2018,A1 .Location in patent: Paragraph 0409-0412

54
[ 30964-00-2 ]
6-amino-1-(4-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-(hydroxymethyl)piperidin-1-yl)hexan-1-one [ No CAS ]
N-(6-(4-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-(hydroxymethyl)piperidin-1-yl)-6-oxohexyl)hept-6-ynamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90.7%		Hept-6-ynoic acid (TCI America, 0.529 g, 4.20 mmol), HOBt (0.643 g, 4.20 mmol) and EDC-HCl (0.805 g, 4.20 mmol) were dissolved in DCM (20 mL) and stirred at room temperature for 30 min. At 0 C. amine 23 (1.960 g, 3.50 mmol) and DIPEA (1.086 g, 8.4 mmol) were added. The reaction mixture was stirred 18 h at room temperature, washed with 5% NaHCO3, 5% HCl, brine, dried over Na2SO4, concentrated and purified on a silica gel column (1-5% MeOH, DCM) to give 2.123 g (90.7%) compound 27b as a white dry foam.

Reference： [1]Patent: US2018/16232,2018,A1 .Location in patent: Paragraph 0253-0254

55
[ 30964-00-2 ]
6-amino-1-(4-(hydroxymethyl)-4-((tris(4-methoxyphenyl)methoxy)methyl)piperidin-1-yl)hexan-1-one [ No CAS ]
N-(6-(4-((tris(4-methoxyphenyl)methoxy)methyl)-4-(hydroxymethyl)piperidin-1-yl)-6-oxohexyl)hept-6-ynamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94.4%		Hept-6-ynoic acid (TCI America, 0.303 g, 2.4 mmol), HOBt (0.367 g, 2.40 mmol) and EDC-HCl ((0.46 g, 2.4 mmol) were dissolved in DCM (20 mL) and stirred at room temperature for 30 min. At 0 C. amine 24 (1.960 g, 2.0 mmol) and DIPEA (0.620 g, 4.8 mmol) were added. The reaction mixture was stirred 18 h at room temperature, washed with 5% NaHCO3, 5% HCl, brine, dried over Na2SO4, concentrated and purified on a silica gel column (1-5% MeOH, DCM) to give 1.320 g (94.4%) compound 28b as a white dry foam.

Reference： [1]Patent: US2018/16232,2018,A1 .Location in patent: Paragraph 0255

56
[ 30964-00-2 ]
3-bromo-N-(2,4,6-trimethylbenzyl)benzenesulfonamide [ No CAS ]
7-(3-(N-(2,4,6-trimethylbenzyl)sulfamoyl)phenyl)hept-6-ynoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,2-dimethoxyethane; water; at 80℃; for 1h;Inert atmosphere; Microwave irradiation;	3-bromo-N-(2,4,6-trimethylbenzyl)benzenesulfonamide (intermediate b, 302 mg, 0.820 mmol), potassium carbonate (397 mg, 2.87 mmol), tetrakis(triphenylphosphoranyl)pailadium (95 mg, 0.082 mmol) and copper(l) iodide (15.63 mg, 0,082 mmol) were suspended in a DME/H2O mixture (1/1 vol.) (2mL). The resulting mixture was stirred under nitrogen for 5 minutes, and <strong>[30964-00-2]hept-6-ynoic acid</strong> (0,212 mL, 1 ,64 mmol) was added. The mixture was irradiated with microwaves for 1 h at 80C. After removing the DME under reduced pressure, the residue was taken with AcOEt (15 mL) and washed with HCI aq 2 (2 x 10 mL) and brine (2 x 10 mL). The organic layer was concentrated under reduced pressure and the residue was purified by semi-preparative HPLC-UV, to afford the product as a colorless oil (206 mg, Y = 61 %). MS (ESI+) m/z: 279.1 [M+H]+.

Reference： [1]Patent: WO2018/29150,2018,A1 .Location in patent: Page/Page column 18

57
[ 30964-00-2 ]
2,3,4,2',3',4'-hexakis-O-(trimethylsilyl)-α,α-trehalose [ No CAS ]
C₃₇H₇₈O₁₂Si₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20℃; for 5h;Inert atmosphere;	An oven-dried round-bottom flask was charged with DCC (1.597 g, 7.738 mmol) and DMAP (0.236 g, 1.935 mmol). After drying the reagents under high vacuum and placing the flask under a nitrogen atmosphere, anhydrous CH2Cl2 (30 mL) was added and the mixture was cooled to 0 C. To the stirring solution was added <strong>[30964-00-2]6-heptynoic acid</strong> (490 muL, 3.869 mmol) followed by slow, dropwise addition of a freshly prepared solution of TMS6-trehalose (3.000 g, 3.869 mmol) in anhydrous CH2Cl2 (30 mL). The reaction mixture was stirred and gradually allowed to warm to room temperature. After 5 h, TLC (hexanes/ethyl acetate 4:1) showed generation of the presumed monoester product (Rf=0.49) and diester product (Rf=0.67). The reaction was quenched by addition of excess CH3OH and concentrated by rotary evaporation. After resuspension of the crude product in CH2Cl2, the insoluble byproduct DCU was removed by filtration. The filtrate containing crude product was concentrated by rotary evaporation and purified by silica gel chromatography (hexanes/ethyl acetate 8:1 containing 1% Et3N) to give the pure monoester intermediate (1.546 g, 45%) as a pale yellow syrup. The intermediate was dissolved in anhydrous CH3OH (500 mL) and placed under a nitrogen atmosphere. Dowex 50WX8-400 H+ ion-exchange resin (8.7 g) was added and the reaction was stirred for 30 min at room temperature, after which TLC (CH2Cl2/CH3OH 2:1) indicated that the reaction was complete (Rf=0.24). After the ion-exchange resin was filtered off, the filtrate was concentrated by rotary evaporation, purified by silica gel chromatography (CH2Cl2/CH3OH 2:1), and filtered to give O-AlkTMM (0.636 g, 75%) as a white solid. O-AlkTMM may also be prepared by direct acylation of trehalose, such that compounds can be formed in one step. This direct acylation of trehalose can be combined with reverse-phase (C18) purification to achieve desired purity. 1H NMR (300 MHz, D2O): delta 5.18 (d, J=4.2 Hz, 1H), 5.16 (d, J=3.6 Hz, 1H), 4.45 (dd, J=1.5, 12.3 Hz, 1H), 4.30 (dd, J=4.8, 12.3 Hz, 1H), 4.03 (m, 1H), 3.90-3.63 (m, 7H), 3.50 (t, J=9.9 Hz, 1H), 3.44 (t, J=9.3 Hz, 1H), 2.48 (t, J=6.9 Hz, 2H), 2.37 (dd, J=1.8, 3.0 Hz, 1H), 2.28-2.22 (m, 2H), 1.74 (pent, J=6.9 Hz, 2H), 1.56 (pent, J=6.9 Hz, 2H). 13C NMR (75 MHz, D2O): delta 176.19, 93.40, 93.23, 85.64, 72.54, 72.31, 72.17, 70.93, 70.87, 69.90, 69.65, 69.59, 69.36, 63.00, 60.46, 33.21, 27.00, 23.43, 17.20. HR ESI MS negative mode: calcd. for C19H29O12 [M-H]- m/z, 449.1659; found, 449.1555. ().

Reference： [1]Patent: US2018/72767,2018,A1 .Location in patent: Paragraph 0201-0204

58
[ 54258-41-2 ]
[ 30964-00-2 ]
N-(1,10-phenanthrolin-5-yl)hept-6-ynamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 24h;	Compound 3 was synthesized through a modification of a procedure reported in the literature [32].<strong>[54258-41-2]5-Amino-1,10-phenanthroline</strong> (488 mg, 2.50 mmol, 1 eq.) was dissolved in DCM (20 mL) atroom temperature. 6-Heptynoic acid (315 mg, 2.50 mmol, 1 eq.) was added, followed by1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDCI, 959 mg, 5.00 mmol, 2.0 eq.)and finally 4-dimethylaminopyridine (DMAP, 305 mg, 2.50 mmol, 1 eq.). The mixture was allowed tostir for 24 h. The solvent was removed under reduced pressure before H2O (50 mL) was added causingprecipitation of a white solid which was isolated by filtration. The resulting solid was redispersed inMeCN (10 mL) and again filtered before being collected by filtration under vacuum and dried underhigh vacuum to give a beige/white solid (637 mg, 2.10 mmol, 84.0%).

Reference： [1]Molecules,2018,vol. 23,p. 1 - 10

59
[ 30964-00-2 ]
[ 540-72-7 ]
(E)-6,7-dithiocyanatohept-6-enoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With Oxone; In dichloromethane; at 20℃; for 2h;	In a 50 mL round bottom flask, 1.26 g of <strong>[30964-00-2]6-heptynoic acid</strong> was added in sequence.1.79 g of sodium thiocyanate, 1.85 g of potassium persulfate complex salt, 15 ml of dichloromethane,The reaction was stirred at room temperature for 2 hours. Filter and remove the solvent under reduced pressure.The target product was separated by silica gel column chromatography, 1.69 g, yield 70%.

Reference： [1]Organic and Biomolecular Chemistry,2018,vol. 16,p. 9064 - 9068
[2]Patent: CN109180546,2019,A .Location in patent: Paragraph 0129; 0130; 0131; 0132

60
[ 30964-00-2 ]
[ 75-65-0 ]
[ 151978-58-4 ]

Reference： [1]Organic Letters,2018,vol. 20,p. 7345 - 7350

61
[ 30964-00-2 ]
(2-(4-(tert-butyl)-2-ethoxyphenyl)-4,5-bis(4-chlorophenyl)-4,5-dihydro-1H-imidazol-1-yl)(piperazin-1-yl)methanone [ No CAS ]
1-(4-(2-(4-(tert-butyl)-2-ethoxyphenyl)-4,5-bis(4-chlorophenyl)-4,5-dihydro-1H-imidazole-1-carbonyl)piperazin-1-yl)hept-6-yn-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%		General procedure: To a solution of alkynoic acid (1.2 equiv.) in DMF was added DIPEA (3 equiv.) at 0C. It was then followed by the addition of HATU (2 equiv.) After being stirred at room temperature for 30min, a solution of amine (1 equiv.) in DMF was added. The reaction mixture was stirred for another 3hat room temperature. The reaction mixture was then diluted with ethyl acetate and the organic phase was washed with water. The collected organic phase was dried over MgSO4, after the filtration and concentration, the residue was submitted to the flash column chromatography for purification (Hex/EA: 1/1 to 1/2), giving the desired compound as a white amorphous solid.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 176,p. 476 - 491

62
[ 30964-00-2 ]
2-amino-1-(4-(2-(4-(tert-butyl)-2-ethoxyphenyl)-4,5-bis(4-chlorophenyl)-4,5-dihydro-1H-imidazole-1-carbonyl)piperazin-1-yl)ethan-1-one [ No CAS ]
N-(2-(4-(2-(4-(tert-butyl)-2-ethoxyphenyl)-4,5-bis(4-chlorophenyl)-4,5-dihydro-1H-imidazole-1-carbonyl)piperazin-1-yl)-2-oxoethyl)hept-6-ynamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%		General procedure: To a solution of alkynoic acid (1.2 equiv.) in DMF was added DIPEA (3 equiv.) at 0C. It was then followed by the addition of HATU (2 equiv.) After being stirred at room temperature for 30min, a solution of amine (1 equiv.) in DMF was added. The reaction mixture was stirred for another 3hat room temperature. The reaction mixture was then diluted with ethyl acetate and the organic phase was washed with water. The collected organic phase was dried over MgSO4, after the filtration and concentration, the residue was submitted to the flash column chromatography for purification (Hex/EA: 1/1 to 1/2), giving the desired compound as a white amorphous solid.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 176,p. 476 - 491

63
[ 26166-92-7 ]
[ 30964-00-2 ]
7-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)hept-6-ynoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%	With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; copper (I) iodide; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 80℃; for 16h;	336.1 Step 1: Synthesis of 7- (2- (2, 6-dioxopiperidin-3-yl) -1, 3-dioxoisoindolin-5-yl) hept-6-ynoic acid A mixture of 5-bromo-2- (2, 6-dioxopiperidin-3-yl) isoindoline-1, 3-dione (100 mg, 298 umol) , Pd (dppf) Cl2(22 mg, 29.8 umol) , hept-6-ynoic acid (56 mg, 447 umol) , CuI (6 mg, 29.8 umol) and DIPEA (116 mg, 894 umol) in DMSO (6 mL) was stirred at 80 for 16 h. The reaction mixture was purified by reverse-phase chromatography to give the desired product (45 mg, 39%yield) as a light yellow solid. MS (ESI) m/z: 381.1 [M-H]-.
39%	With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; copper (I) iodide; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 80℃; for 16h;	336.1 Step 1: Synthesis of 7- (2- (2, 6-dioxopiperidin-3-yl) -1, 3-dioxoisoindolin-5-yl) hept-6-ynoic acid A mixture of 5-bromo-2- (2, 6-dioxopiperidin-3-yl) isoindoline-1, 3-dione (100 mg, 298 umol) , Pd (dppf) Cl2(22 mg, 29.8 umol) , hept-6-ynoic acid (56 mg, 447 umol) , CuI (6 mg, 29.8 umol) and DIPEA (116 mg, 894 umol) in DMSO (6 mL) was stirred at 80 for 16 h. The reaction mixture was purified by reverse-phase chromatography to give the desired product (45 mg, 39%yield) as a light yellow solid. MS (ESI) m/z: 381.1 [M-H]-.

Reference： [1]Current Patent Assignee: CULLGEN SHANGHAI - WO2020/200291, 2020, A1 Location in patent: Page/Page column 171
[2]Current Patent Assignee: CULLGEN SHANGHAI - WO2022/68933, 2022, A1 Location in patent: Page/Page column 156

64
[ 26166-92-7 ]
[ 30964-00-2 ]
7-(2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-5-yl)heptanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; copper (I) iodide; N-ethyl-N,N-diisopropylamine / dimethyl sulfoxide / 16 h / 80 °C 2: palladium on activated charcoal; hydrogen / methanol / 16 h / 25 °C
	Multi-step reaction with 2 steps 1: palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; N-ethyl-N,N-diisopropylamine; copper (I) iodide / dimethyl sulfoxide / 16 h / 80 °C 2: palladium on activated charcoal; hydrogen / methanol / 16 h / 25 °C

Reference： [1]Current Patent Assignee: CULLGEN SHANGHAI - WO2020/200291, 2020, A1
[2]Current Patent Assignee: CULLGEN SHANGHAI - WO2022/68933, 2022, A1

65
[ 1010100-26-1 ]
[ 30964-00-2 ]
7-(2-(2,6-dioxopiperidin-3-yl)-1-oxoisoindolin-5-yl)hept-6-ynoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; copper (I) iodide; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 80℃; for 16h;	338.1 Step 1: Synthesis of 7- (2- (2, 6-dioxopiperidin-3-yl) -1-oxoisoindolin-5-yl) hept-6-ynoic acid A mixture of 3- (5-bromo-1-oxoisoindolin-2-yl) piperidine-2, 6-dione (100 mg, 311 umol) , Pd (dppf) Cl2(23 mg, 31.1 umol) , hept-6-ynoic acid (59 mg, 467 umol) , CuI (6 mg, 31.1 umol) and DIPEA (120 mg, 931 umol) in DMSO (6 mL) was stirred at 80 for 16 h. The reaction mixture was purified by reverse-phase chromatography to give the desired product (51 mg, 45%yield) as a light yellow solid. MS (ESI) m/z: 367.1 [M-H]-.
45%	With palladium (II) [1,1'-bis(diphenylphosphanyl)ferrocene] dichloride; copper (I) iodide; N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 80℃; for 16h;	338.1 Step 1: Synthesis of 7- (2- (2, 6-dioxopiperidin-3-yl) -1-oxoisoindolin-5-yl) hept-6-ynoic acid A mixture of 3- (5-bromo-1-oxoisoindolin-2-yl) piperidine-2, 6-dione (100 mg, 311 umol) , Pd (dppf) Cl2(23 mg, 31.1 umol) , hept-6-ynoic acid (59 mg, 467 umol) , CuI (6 mg, 31.1 umol) and DIPEA (120 mg, 931 umol) in DMSO (6 mL) was stirred at 80 for 16 h. The reaction mixture was purified by reverse-phase chromatography to give the desired product (51 mg, 45%yield) as a light yellow solid. MS (ESI) m/z: 367.1 [M-H]-.

Reference： [1]Current Patent Assignee: CULLGEN SHANGHAI - WO2020/200291, 2020, A1 Location in patent: Page/Page column 172
[2]Current Patent Assignee: CULLGEN SHANGHAI - WO2022/68933, 2022, A1 Location in patent: Page/Page column 157

66
[ 30964-00-2 ]
[ 75-03-6 ]
[ 105339-02-4 ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium carbonate In N,N-dimethyl-formamide Inert atmosphere;	4.1 Example 4 First step:To a solution of 6-heptynoic acid (3.0 g, 23.8 mmol) in dry DMF (40 mL) was added K2CO3 (3.9 g, 28.57 mmol) and iodoethane (4.45 g, 28.57 mmol). The reaction was stirred under N2 overnight. The reaction was then poured into 50 mL EA and extracted with 20 mL H2O. The aqueous layer was extracted with additional organics (2 x 25 mL CH2Cl2, 1 x 25 mL Et2O). The combined organic layers were dried over anhydrous MgSO4, filtered and concentrated, and the resulting concentrate was purified by flash chromatography with PE to obtain compound 9 (2.1 g, 13.6 mmol, 70%).

Reference： [1]Current Patent Assignee: SOUTH UNIV - CN114516789, 2022, A Location in patent: Paragraph 0095-0097

67
[ 30964-00-2 ]
[ 7149-10-2 ]
C₁₅H₁₉NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With benzotriazol-1-ol; N-[3-(N,N-dimethylamino)-propyl]-N'-ethyl-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In acetonitrile at 30℃; for 18h; Inert atmosphere;	5; 106 The preparation method of capsaicin derivatives shown in formula II-3 above, comprising the following steps: In the reaction vessel were added 5-(aminomethyl)-2-methoxyphenol hydrochloride, alkali, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, 1-hydroxybenzotriazole, alkyne acid and organic solvent, reacted at 30 °C for 18 hours to obtain the reaction liquid, to be cooled to room temperature, vacuum concentrated, the residue over 250 mesh silicone column chromatography is given white solid is given the capsaicin derivative shown in formula II-3, the yield is 73%, wherein: Silica gel column chromatography uses a mixture of petroleum ether and ethyl acetate in a volume ratio of 10:1 as the eluent; 5-(Aminomethyl)-2-methoxyphenol hydrochloride, alkali, 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, 1-hydroxybenzotriazole, alkyne acid, organic solvent molar ratio of 1:4:1.5:1.5:1:1:30. Further, the base is N,N- diisopropylethylamine. Further, the organic solvent is acetonitrile.

Reference： [1]Current Patent Assignee: INST CHINESE MATERIA MEDICA CHINA ACADEMY OF CMS - CN114524747, 2022, A Location in patent: Paragraph 0050-0055; 0092-0095

68
[ 30964-00-2 ]
[ 61869-08-7 ]
[ CAS Unavailable ]

Yield	Reaction Conditions	Operation in experiment
65%	With 4-dimethylaminopyridine; dicyclohexyl-carbodiimide In dichloromethane at 25℃;

Reference： [1]Ji, Xiaolei; Shen, Chaoren; Tian, Xinxin; Zhang, Hongru; Ren, Xinyi; Dong, Kaiwu [Angewandte Chemie - International Edition, 2022, vol. 61, # 29][Angew. Chem., 2022, vol. 134, # 29]

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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. 30964-00-2 ] {[proInfo.proName]}

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[ 30964-00-2 ] Synthesis Path-Upstream 1~1

[ 30964-00-2 ] Synthesis Path-Downstream 1~68

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Alkynes

Aliphatic Chain Hydrocarbons

Carboxylic Acids

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[ 30964-00-2 ]