[ CAS No. 764-85-2 ] {[proInfo.proName]}

Name: 764-85-2|Nonanoylchloride|99%
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Quality Control of [ 764-85-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 764-85-2 ]

Product Details of [ 764-85-2 ]

CAS No. :	764-85-2	MDL No. :	MFCD00000768
Formula :	C₉H₁₇ClO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NTQYXUJLILNTFH-UHFFFAOYSA-N
M.W :	176.68	Pubchem ID :	69819
Synonyms :		Chemical Name :	Nonanoylchloride

Calculated chemistry of [ 764-85-2 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.89
Num. rotatable bonds :	7
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	50.37
TPSA :	17.07 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) :	-4.25 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.83
Log Po/w (XLOGP3) :	4.4
Log Po/w (WLOGP) :	3.5
Log Po/w (MLOGP) :	2.7
Log Po/w (SILICOS-IT) :	3.32
Consensus Log Po/w :	3.35

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.25
Solubility :	0.1 mg/ml ; 0.000568 mol/l
Class :	Soluble
Log S (Ali) :	-4.48
Solubility :	0.00591 mg/ml ; 0.0000335 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-3.66
Solubility :	0.0384 mg/ml ; 0.000217 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	2.1

Safety of [ 764-85-2 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P261-P271-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338	UN#:	3265
Hazard Statements:	H314-H335	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 764-85-2 ]

* 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 [ 764-85-2 ]
Downstream synthetic route of [ 764-85-2 ]

[ 764-85-2 ] Synthesis Path-Upstream 1~5

1
[ 764-85-2 ]
[ 123-29-5 ]

Reference： [1] Tetrahedron Letters, 1980, vol. 21, p. 3147 - 3150

2
[ 764-85-2 ]
[ 64-17-5 ]
[ 123-29-5 ]

Reference： [1] Chinese Journal of Chemistry, 2011, vol. 29, # 10, p. 2153 - 2156

3
[ 764-85-2 ]
[ 1196-92-5 ]
[ 2444-46-4 ]

Yield	Reaction Conditions	Operation in experiment
88.6%	With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;	To a solution of the hydrochloride or hydrobromide salt of an amine (1 mmol) in anhydrous N,N- dimethylformamide (DMF) (2 mL) was added N, N- diisopropylethylamine (DIPEA) (2 mmol) to liberate the amine. After stirring at room temperature for 10 min, nonanoyl chloride (1 mmol) was added. The solution was stirred at room temperature for 6 to 24 h. After the reaction, water (40 mL) was added to the solution. The reaction mixture was transferred to a separating funnel and extracted with dichloromethane, CH₂Cl₂ (3 * 6 mL) . The organic extracts were concentrated under reduced pressure to give a crude product. The crude product was then purified by silica gel column chromatography (using hexane/ethyl acetate, 2:1 v/v, as eluent) or preparative HPLC (using the protocol set out in "Analytical Protocols" above) to give the final product.

Reference： [1] Advanced Synthesis and Catalysis, 2014, vol. 356, # 9, p. 2113 - 2118
[2] Patent: WO2010/144055, 2010, A1, . Location in patent: Page/Page column 45-46; 50
[3] Journal of Medicinal Chemistry, 1993, vol. 36, # 18, p. 2595 - 2604
[4] Recueil des Travaux Chimiques des Pays-Bas, 1934, vol. 53, p. 855
[5] Journal of the American Chemical Society, 1919, vol. 41, p. 2121[6] Journal of the American Chemical Society, 1920, vol. 42, p. 597
[7] Journal of Medicinal Chemistry, 1993, vol. 36, # 16, p. 2362 - 2372

4
[ 764-85-2 ]
[ 7149-10-2 ]
[ 2444-46-4 ]

Yield	Reaction Conditions	Operation in experiment
91.5%	With sodium hydrogencarbonate In dichloromethane; water at 20 - 42℃; for 2.5 h;	1) Preparation of crude product mixture: 105 g of vanillinamine hydrochloride was added to a mixture consisting of 200 g of sodium hydrogencarbonate, 500 mL of dichloromethane and 600 mL of water, and the mixture was stirred well and the mixture was further heated at room temperature (Methylene chloride: volume: 146.4 mL) was added dropwise over 1 hour. After completion of the dropwise addition, the temperature was raised to 42 ° C and maintained at that temperature for 1.5 hours. To obtain a crude product mixture (1420 mL);(2) Crystallization purification: The crude product mixture was cooled to room temperature, first using 200 mL of 25percentHydrochloric acid solution was shaken and allowed to stand for separation. The organic phase was separated (about 750 mL), and 150 mL of a 20percentOf the sodium hydroxide solution was shaken and the organic phase was washed and allowed to stand for separation. The organic phase was separated again750 mL), washed with 200 mL of water, and partitioned. After washing with water, the organic phase (about 750 mL)150 mL of methylene chloride was distilled off to give a concentrated organic phase (ca. 600 mL), which was added to the concentrated organic phase1080mL petroleum ether after cooling crystallization, cooling rate of 0.25 / min, crystallization termination temperature of aboutAt -10 & lt; 0 & gt; C, maintaining the crystallization termination temperature for at least 30 min, filtering at the crystallization termination temperature,Dried to obtain solid synthetic capsaicin 148.6g, the yield was 91.5percent, by high performance liquid chromatography(HPLC) to determine the purity of 99.5percent.

Reference： [1] Patent: , 2016, , . Location in patent: Paragraph 0040; 0041; 0042
[2] Journal of Agricultural and Food Chemistry, 2010, vol. 58, # 6, p. 3342 - 3349

5
[ 764-85-2 ]
[ 2444-46-4 ]

Reference： [1] Annales pharmaceutiques françaises, 1959, vol. 17, p. 453 - 455

[ 764-85-2 ] Synthesis Path-Downstream 1~88

2
[ 764-85-2 ]
[ 1196-92-5 ]
[ 2444-46-4 ]

Yield	Reaction Conditions	Operation in experiment
88.6%	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃;	To a solution of the hydrochloride or hydrobromide salt of an amine (1 mmol) in anhydrous N,N- dimethylformamide (DMF) (2 mL) was added N, N- diisopropylethylamine (DIPEA) (2 mmol) to liberate the amine. After stirring at room temperature for 10 min, nonanoyl chloride (1 mmol) was added. The solution was stirred at room temperature for 6 to 24 h. After the reaction, water (40 mL) was added to the solution. The reaction mixture was transferred to a separating funnel and extracted with dichloromethane, CH2Cl2 (3 * 6 mL) . The organic extracts were concentrated under reduced pressure to give a crude product. The crude product was then purified by silica gel column chromatography (using hexane/ethyl acetate, 2:1 v/v, as eluent) or preparative HPLC (using the protocol set out in "Analytical Protocols" above) to give the final product.

Reference： [1]Advanced Synthesis and Catalysis,2014,vol. 356,p. 2113 - 2118
[2]Patent: WO2010/144055,2010,A1 .Location in patent: Page/Page column 45-46; 50
[3]Journal of Medicinal Chemistry,1993,vol. 36,p. 2595 - 2604
[4]Recueil des Travaux Chimiques des Pays-Bas,1934,vol. 53,p. 855
[5]Journal of Medicinal Chemistry,1993,vol. 36,p. 2362 - 2372

3
[ 764-85-2 ]
[ 38948-27-5 ]
nonanoic acid-[4-(2-piperidino-ethoxy)-anilide] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With butanone

Reference： [1]Chabrier et al. [Bulletin de la Societe Chimique de France, 1955, p. 1603,1606]

4
[ 112-05-0 ]
[ 764-85-2 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride;N,N-dimethyl-formamide; at 50℃; for 2.25h;	Example 9 Purification of Pelargonoyl chloride (Nonanoyl Chloride) 0.4 g (0.005 mol) of N,N-dimethylformamide were added to 158 g (1.0 mol) of pelargonic acid, and the mixture was heated to 50 C. At 50 C., a total of 125 g (1.05 mol) of thionyl chloride were added dropwise over the course of 45 minutes.. After a post reaction time of 30 minutes at 50 C., nitrogen was passed through the mixture at 50 C. for 1 hour, and sulfur dioxide, hydrogen chloride gas and unreacted thionyl chloride were stripped out.. The pale yellow product had a color number of 113 APHA and, according to GC analysis, comprised 99.5 area % of pelargonoyl chloride. 20 ml of the product were vigorously stirred with 5 ml of DMF hydrochloride from synthesis 1 in a stirred apparatus, and then the phases were separated.. The pelargonoyl chloride phase was stripped until HCl-free using nitrogen.. The color number was then only 37 APHA.
	With phosgene;N,N-dimethyl-formamide; at 20 - 30℃;	100.5 g (1.38 mol) of N,N,-dimethylformamide were added to 2.75 mol of pelargonic acid in a stirred apparatus.. The reaction solution was brought to a temperature of from 20 to 30 C. with stirring, and a total of 2.78 mol of gaseous phosgene were introduced under atmospheric pressure.. After the addition of phosgene was complete, the two phases were separated from one another.. The catalyst phase comprised a molar proportion of the catalyst adduct, based on the molar amount of N,N-dimethylformamide plus catalyst adduct, of <0.05.. The carbonyl chloride phase comprised 97.1 area % of pelargonoyl. chloride and 1.9 area % of pelargonic anhydride.. The color number was 16 APHA. As a result of a very low, virtually stoichiometric molar ratio between the phosgene introduced and the pelargonic acid used, only an unsatisfactorily low content of pelargonoyl chloride was achieved in the crude product, with too high a content of pelargonic anhydride.. However, the carbonyl-chloride-containing phase exhibits a very low color number.
	With hydrogenchloride; phosgene;N,N-dimethyl-formamide; at 20 - 30℃;	100.5 g (1.38 mol) of N,N-dimethylformamide were added to 2.75 mol of pelargonic acid in a stirred apparatus.. The reaction solution was brought to a temperature of from 20 to 30 C. with stirring, and a total of 2.78 mol of gaseous phosgene and simultaneously 1.92 mol of gaseous hydrogen chloride were introduced under atmospheric pressure.. When the addition of phosgene and hydrogen chloride was complete, the two phases were separated from one another.. The catalyst phase comprised a molar proportion of the catalyst adduct, based on the molar amount of N,N-dimethylformamide plus catalyst adduct, of 1%.. The carbonyl chloride phase comprised 98.9% by weight of pelargonoyl chloride and 0.04% by weight of pelargonic anhydride.. The color number was 18 APHA. Only as a result of the simultaneous introduction of hydrogen chloride according to the invention was it possible to obtain a high conversion to pelargonoyl chloride having a very low color number.

	With oxalyl dichloride; In dichloromethane; at 0 - 20℃; for 2h;	A solution of 2-(oxazol-5-yl)pyridine (117 mg, 0.80 mmol) in anhydrous THF (5 mL) cooled to -75 C. under N2 was treated with n-BuLi (2.5 M in hexanes, 1.1 equiv, 0.88 mmol, 0.35 mL), and stirred for 20 min. ZnCl2 (0.5 M in THF, 2.0 equiv, 1.60 mmol, 3.2 mL) was added at -75 C., and stirred for 45 min at 0 C. Cul (1.0 equiv, 0.80 mmol, 152 mg) was added, and the solution was stirred for 10 min at 0 C. A separate flask was charged with nonanoic acid (2 equiv, 1.60 mmol, 253 mg, 0.28 mL) in anhydrous CH2Cl2 (4.2 mL), and to this solution cooled to 0 C. under N2 was added oxalyl chloride (5 equiv, 8.0 mmol, 1.02 g, 0.70 mL). After stirring at rt for 2 h, the solution was concentrated under reduced pressure and dissolved in anhydrous THF (1.5 mL). The solution of nonanoyl chloride was added and the solution was stirred for 1 h at 0 C. The reaction was diluted with EtOAc (10 mL), and washed with 15% aqueous NH4OH (1×10 mL), H2O (1×10 mL), and saturated aqueous NaCl (1×10 mL). The organic layer was dried (Na2SO4), filtered, and concentrated under reduced pressure. Flash chromatography (SiO2, 2.5 cm×17.5 cm, 20% EtOAc-hexanes) afforded 1-(5-(pyridin-2-yl)oxazol-2-yl)nonan-1-one (188) (94 mg, 0.33 mmol, 41% yield) as a light brown powder: mp 56-57 C.; 1H NMR (CDCl3, 250 MHz) d 8.61 (br d, J=4.4 Hz, 1H), 7.84-7.71 (m, 3H), 7.29-7.22 (m, 1H), 3.05 (t, J=7.3 Hz, 2H), 1.79-1.66 (m, 2H), 1.42-1.16 (m, 10H), 0.88-0.77 (m, 3H); 13C NMR (CDCl3, 62.5 MHz) d 188.4, 157.3, 153.1, 150.0, 146.2, 137.0, 126.8, 124.0, 120.3, 39.0, 31.7, 29.2, 29.0, 24.0, 23.9, 22.5, 14.0; IR (KBr) umax 2922, 2856, 1705, 1697, 1600, 1420, 1381 cm-1; MALDI-FTMS (DHB) m/z 287.1744 (C17H22N2O2+H+ requires 287.1754).
	With thionyl chloride; at 80℃; for 16h;	General procedure: In a 250 ml round bottom flask dried previously, wasadded 1 ml of nonanoic acid (11 mmol) and 0.6 ml of thionylchloride (8.30 mmol), the reaction mixturewas stirred and refluxedfor 16 h at 80 C. Later, the reaction mixture was cooled at roomtemperature and under vigorous stirring was rapidly added 6(0.89 mmol, 200 mg) to reaction medium, followed of 2 ml ofpyridine. The mixture reaction was stirred at room temperature for2 h and then partitioned between an aqueous acid solution anddichloromethane; the organic layerwas extracted and washed witha saturated aqueous solution of sodium chloride. After theconcentrated organic layer was hydrolyzed in presence 2 ml of asolution sodium hydroxide 0.1 M in 10 ml of methanol and wasrefluxed for 3 h under stirring. The hydrolysis mixturewas acidifieduntil pH 4 with hydrochloric acid 37%, a white precipitate wasformed and then filtered followed of the purification by columnchromatography using 20% ethyl acetate/hexane, and finally theproduct obtained was crystallized in 1:4 water/methanol to give 8as white crystals.
	With trichloroacetamide; triphenylphosphine; In dichloromethane; for 1h;Reflux;	General procedure: To a 250-mL round-bottomed flask was added the corresponding carboxylic acid (25 mmol), trichloroacetamide (8.12 g, 50 mmol), triphenylphosphine (13.11 g,50 mmol), and dichloromethane (100 mL) to give a colorless solution. The mixture was stirred and heated at reflux for 1 h. Then, solketal (3.11 mL, 25 mmol) and pyridine (6.04 mL, 75 mmol) were added to the resulting acid chloride solution and the reaction mixture was heated at reflux until completion as indicated by TLC (approximately 4 h). After completion, the solution was extracted with 10% HCl and sat. aq. NaHCO3, dried over Na2SO4 and evaporated. The crude product was purified with a silica gel column eluting with 5% EtOAc/hexane (Scheme 2).
	With oxalyl dichloride; In dichloromethane; at 0 - 20℃; for 2h;Inert atmosphere;	In a 2 liter, two neck round bottom flask, 20 g octanoic acid dissolved in DCM (200 ml) was taken and then added 1.5 eq. oxalyl chloride slowly at 0 C., stirring under nitrogen atmosphere. The resulting reaction mixture was stirred at room temperature for 2 hours.
	With thionyl chloride;Reflux;	General procedure: 45 g (50 mL, 0.346 mol) of enanthic acid was slowly added dropwise to 124 g (75 mL,1.042 mol) of thionyl chloride upon reflux. The obtained mixture was heated upon reflux for 30 min, and the excess thionyl chloride was evaporated in vacuum. About 50 g of enanthoyl chloride was obtained as a yellow oil. 25 g (0.102 mol) of 5,7-dimethyl-1,3-bis(hydroxymethyl)adamantane, 70 mL of triethylamine, 50 g (0.337 mol) of enanthoyl chloride, and 200 mL of toluene are placed into a three-neck flask equipped with a mechanical stirrer and a reflux condenser. The obtained mixture is heated upon reflux for 3 h. The formed precipitate of triethylamine hydrochloride is filtered off, and the filtrate is evaporated in vacuum on a rotary evaporator. The residue is purified via vacuum distillation collecting a fraction with bp 200-202C (0.036 Torr). The weight 37 g, yield 74%,

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 5895 - 5899
[2]Transactions of the Royal Society of Canada = Memoires de la Societe royale du Canada,1933,vol. <3>27 III,p. 99,101
 Chemisches Zentralblatt,1934,vol. 105,p. 1964
[3]Transactions of the Royal Society of Canada = Memoires de la Societe royale du Canada,1933,vol. <3>27 III,p. 99,101
 Chemisches Zentralblatt,1934,vol. 105,p. 1964
[4]Fette und Seifen,1957,vol. 59,p. 946,951
[5]Journal of Organic Chemistry,1976,vol. 41,p. 3452 - 3455
[6]Molecular Crystals and Liquid Crystals (1969-1991),1990,vol. 182,p. 201 - 207
[7]Chemical and pharmaceutical bulletin,1984,vol. 32,p. 2687 - 2699
[8]Journal of Medicinal Chemistry,1993,vol. 36,p. 2595 - 2604
[9]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1994,vol. 33,p. 266 - 268
[10]Bioscience, Biotechnology and Biochemistry,1995,vol. 59,p. 602 - 609
[11]Journal of Medicinal Chemistry,2005,vol. 48,p. 1849 - 1856
[12]Russian Journal of Applied Chemistry,2006,vol. 79,p. 1035 - 1037
[13]Patent: US6727384,2004,B1 .Location in patent: Page column 12
[14]Patent: US6770783,2004,B1 .Location in patent: Page column 10-11
[15]Patent: US6770783,2004,B1 .Location in patent: Page column 11
[16]Patent: US2006/111359,2006,A1 .Location in patent: Page/Page column 9
[17]Journal of Natural Products,2005,vol. 68,p. 1380 - 1385
[18]Synthetic Communications,2008,vol. 38,p. 2845 - 2856
[19]Journal of Agricultural and Food Chemistry,2008,vol. 56,p. 4219 - 4224
[20]Letters in drug design and discovery,2010,vol. 7,p. 265 - 268
[21]Journal of Chemical Research,2011,vol. 35,p. 703 - 706
[22]Chinese Journal of Chemistry,2011,vol. 29,p. 2153 - 2156
[23]European Journal of Medicinal Chemistry,2013,vol. 66,p. 193 - 203
[24]Advanced Synthesis and Catalysis,2014,vol. 356,p. 2113 - 2118
[25]Journal of the Chemical Society of Pakistan,2014,vol. 36,p. 462 - 472
[26]Crystal Growth and Design,2014,vol. 14,p. 4944 - 4954
[27]Archiv der Pharmazie,2014,vol. 347,p. 885 - 895
[28]Journal of Lipid Research,2015,vol. 56,p. 2029 - 2039
[29]Journal of Chemical Sciences,2015,vol. 127,p. 1627 - 1635
[30]Chemistry and Physics of Lipids,2016,vol. 201,p. 1 - 10
[31]Chemical Communications,2017,vol. 53,p. 8675 - 8678
[32]Research on Chemical Intermediates,2018,vol. 44,p. 1305 - 1323
[33]Patent: US2018/169268,2018,A1 .Location in patent: Paragraph 0025; 0344; 0345
[34]Petroleum Chemistry,2018,vol. 58,p. 687 - 693
 Neftekhimiya,2018,vol. 58
[35]Journal of Biomolecular Structure and Dynamics,2020

5
[ 764-85-2 ]
[ 109-89-7 ]
[ 10385-09-8 ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 6578 - 6581
[2]Organic Letters,2020
[3]Journal of the American Chemical Society,1954,vol. 76,p. 3730
[4]Annales de Chimie (Cachan, France),1930,vol. <10>13,p. 62,69,97,129
Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1928,vol. 186,p. 876

6
[ 764-85-2 ]
[ 5344-44-5 ]
[ 5540-64-7 ]

Reference： [1]Journal of Medicinal Chemistry,1966,vol. 9,p. 428 - 430

8
[ 764-85-2 ]
[ 121-01-7 ]
[ 13277-18-4 ]

Reference： [1]Journal of Medicinal Chemistry,1967,vol. 10,p. 93 - 95

9
[ 764-85-2 ]
[ 2130-77-0 ]
N^γ-Benzyloxycarbonyl-N^α-pelargonyl-L-α,γ-diamino-buttersaeure [ No CAS ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1965,vol. 30,p. 2410 - 2433

10
[ 764-85-2 ]
[ 13852-51-2 ]
[ 5942-09-6 ]

Reference： [1]Journal of Medicinal Chemistry,1966,vol. 9,p. 428 - 430

11
[ 764-85-2 ]
[ 40787-96-0 ]
[ 5540-59-0 ]

Reference： [1]Journal of Medicinal Chemistry,1966,vol. 9,p. 428 - 430

12
[ 764-85-2 ]
[ 66-84-2 ]
Nonanoic acid ((3R,4R,5S,6R)-2,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-amide [ No CAS ]

Reference： [1]Carbohydrate Research,1976,vol. 47,p. 188 - 194

13
[ 764-85-2 ]
[ 10212-25-6 ]
(3aS)-3c-nonanoyloxy-2t-nonanoyloxymethyl-(3ar,9ac)-2,3,3a,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-ylideneamine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1976,vol. 19,p. 663 - 667

14
[ 764-85-2 ]
[ 25691-37-6 ]
N(α)-tert. Butyloxycarbonyl-N(γ)-pelargonyl-L-α,γ-diamino-buttersaeure [ No CAS ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1966,vol. 31,p. 2955 - 2972

15
[ 109-97-7 ]
[ 764-85-2 ]
[ 89631-85-6 ]

Yield	Reaction Conditions	Operation in experiment
68%		Aluminum() chloride (8.0 g, 60 mmol) was mixedwith dry dichloromethane (450 mL) in a two-necked flask under N2. <strong>[764-85-2]Nonanoyl chloride</strong>(9.0 mL, 50 mmol) was added dropwise to the solution under stirring. After stirring forseveral minutes, pyrrole (3.7 mL, 55 mmol) dissolved in dry dichloromethane (50 mL)was added and the solution was stirred overnight at room temperature. The reactionwas quenched with 1 M aqueous HCl under cooling. The mixture was extracted withdichloromethane; the organic layer was washed with distilled water and brine, anddried over anhydrous Na2SO4. The solvents were removed under reduced pressure andthe crude product was purified using silica-gel column chromatography(dichloromethane 100%) to yield 4 as a red-orange solid (7.0 g, 68%).1H NMR (500 MHz, CDCl3): delta = 9.36 (brs, 1H, NH), 7.02 (m, 1H, Py), 6.91(m, 1H, Py),6.27(m, 1H, Py), 2.75 (t, J = 7.57 Hz, 2H, CH2), 1.68-1.75 (m, 2H, CH2), 1.24-1.39 (m,10H, C5H10), 0.88 (t, J = 6.94 Hz, 3H, CH3). Elemental analysis calcd (%) for C13H21NO:C 75.32, H 10.21, N 6.76; found: C 74.70, H 10.22, N 6.49.

Reference： [1]Chemistry Letters,2017,vol. 46,p. 260 - 262
[2]Australian Journal of Chemistry,1984,vol. 37,p. 227 - 230

16
[ 101-55-3 ]
[ 764-85-2 ]
4-bromophenyl-4'-nonanoylphenylether [ No CAS ]

Reference： [1]Molecular Crystals and Liquid Crystals (1969-1991),1980,vol. 59,p. 273 - 288

17
[ 764-85-2 ]
[ 61439-59-6 ]
[ 137422-37-8 ]

Reference： [1]Molecular Crystals and Liquid Crystals (1969-1991),1991,vol. 206,p. 103 - 116

18
[ 764-85-2 ]
[ 1568-80-5 ]
[ 121073-39-0 ]

Reference： [1]Journal of the American Chemical Society,1989,vol. 111,p. 4953 - 4959

19
[ 764-85-2 ]
[ 41604-19-7 ]
[ 116831-26-6 ]

Reference： [1]Molecular Crystals and Liquid Crystals (1969-1991),1988,vol. 158,p. 209 - 240

20
[ 764-85-2 ]
[ 4877-80-9 ]
[ 70351-95-0 ]

Reference： [1]Molecular Crystals and Liquid Crystals (1969-1991),1986,vol. 137,p. 381 - 390

21
[ 764-85-2 ]
[ 3102-70-3 ]
[ 107976-25-0 ]

Reference： [1]Canadian Journal of Chemistry,1988,vol. 66,p. 1867 - 1871

22
[ 764-85-2 ]
[ 52806-53-8 ]
[ 110990-17-5 ]

Reference： [1]Pharmaceutical Chemistry Journal,1987,vol. 21,p. 418 - 422
Khimiko-Farmatsevticheskii Zhurnal,1987,vol. 21,p. 681 - 685

23
[ 764-85-2 ]
[ 3811-73-2 ]
[ 111916-74-6 ]

Yield	Reaction Conditions	Operation in experiment
61%	With dmap In benzene 1) 0 deg C, 3 h, 2) RT, 1 h;

Reference： [1]Newcomb, Martin; Sanchez, Robert M.; Kaplan, Jere [Journal of the American Chemical Society, 1987, vol. 109, # 4, p. 1195 - 1199]

24
[ 764-85-2 ]
[ 33588-54-4 ]
[ 133950-70-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide 2.) 4 deg C, overnight; Yield given. Multistep reaction;

Reference： [1]Agban; Ounanian; Luu-Duc; Monget [European Journal of Medicinal Chemistry, 1990, vol. 25, # 8, p. 697 - 699]

25
[ 764-85-2 ]
[ 3030-06-6 ]
[ 133950-77-3 ]

Reference： [1]European Journal of Medicinal Chemistry,1990,vol. 25,p. 697 - 699

26
[ 764-85-2 ]
[ 24155-42-8 ]
1-[2,4-dichloro-β-(n-octylcarbonyloxy)phenethyl]imidazole [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,1994,vol. 29,p. 701 - 706

27
[ 764-85-2 ]
[ 1081-34-1 ]
[ 188917-62-6 ]

Reference： [1]Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals,1995,vol. 264,p. 227 - 230
[2]Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals,1995,vol. 265,p. 61 - 76

28
[ 496-15-1 ]
[ 764-85-2 ]
[ 438542-03-1 ]

Yield	Reaction Conditions	Operation in experiment
95%	With triethylamine; In dichloromethane; at 0℃;Inert atmosphere;	General procedure: Acid chloride (10 mmol) was dissolved in 40 mL DCM in a flame-dried round bottom flask andcooled to 0 C. Then, Indoline (1.12 mL, 10 mmol) and Et3N (1.53 mL, 11 mmol) were added, the ice bath was removed and the slurry was stirred overnight. The mixture was poured into 1 N HCl(100 mL), and extracted with DCM (3 x 50 mL). The combined organic layers were dried with MgSO4, concentrated and purified via column chromatography (silica gel, 20-25% EtOAc in heptanes) and additionally recrystallized from DCM/heptanes to afford the pure amides.

Reference： [1]Chem,2019,vol. 5,p. 1883 - 1891
[2]Bioorganic and medicinal chemistry letters,1999,vol. 9,p. 1869 - 1874

29
[ 764-85-2 ]
[ 28319-77-9 ]
C₁₇H₃₆NO₇P [ No CAS ]

Reference： [1]Chemistry and Physics of Lipids,2007,vol. 147,p. 113 - 118

30
[ 1076-38-6 ]
[ 764-85-2 ]
[ 20924-69-0 ]

Yield	Reaction Conditions	Operation in experiment
84%	With pyridine; at 20℃; for 0.166667h;	General procedure: A mixture of acyl chloride (1 mmol) and 4-hydroxycoumarin(1 mmol) dissolved in dry pyridine (5 mL), was stirred at roomtemperature for 10 min, then water was added till precipitatesare formed. Precipitates are filtered on suction and then washedwith excess of cold water followed by EtOH. Crude products werethen recrystallized from ethanol to obtain pure products in excellent yields.

Reference： [1]Bioorganic Chemistry,2016,vol. 66,p. 111 - 116
[2]Journal of Natural Products,2004,vol. 67,p. 2108 - 2110

31
[ 764-85-2 ]
[ 123-29-5 ]

Reference： [1]Tetrahedron Letters,1980,vol. 21,p. 3147 - 3150

32
[ 764-85-2 ]
[ 2444-46-4 ]

Reference： [1]Annales Pharmaceutiques Francaises,1959,vol. 17,p. 453 - 455

33
[ 764-85-2 ]
[ 825-90-1 ]
[ 181213-09-2 ]

Yield	Reaction Conditions	Operation in experiment
94.7 - 95.2%	With diethylene glycol dimethyl ether; In isopar G; at 80 - 120℃; for 2.5h;	98.1 g (0.5 mol) of dried phenolsulfonate sodium, prepared according to Example 1b, were introduced into 135 g of ISOPAR G and heated to 120 C. 15 g of diethyleneglycol-dimethylether were added. 114.8 g (0.65 mol) of nonanoyl chloride were then added dropwise over the course of 30 min, and the mixture was after-stirred at 120 C. The HCl gas which formed during the reaction was withdrawn. The reaction mixture was cooled after 2 h to 80 C. and filtered through a filter. The white reaction product was then washed twice with a small amount of ISOPAR G and then dried overnight in a drying cabinet at 110-130 C. Gross yield: 165.1 g (yield 98.1% weight) of a white powder with a nonanoyloxybenzenesulfonate sodium (NOBS) content of 96.5%. Net yield of pure NOBS: 94.7% by weight. The mother liquor could be used for the subsequent batch without further purification.Example 4 [0037] 98.1 g (0.5 mol) of dried phenolsulfonate sodium, prepared according to Example 1b, were introduced into 140 g of ISOPAR G and heated to 120 C. 10 g of diethyleneglycol -dimethylether were added. 114.8 g (0.65 mol) of nonanoyl chloride were then added dropwise over the course of 30 min, and the mixture was after-stirred at 120 C. The HCl gas which formed during the reaction was withdrawn. The reaction mixture was cooled after 2 h to 80 C. and filtered through a filter. The white reaction product was then washed twice with a small amount of ISOPAR G and then dried overnight in a drying cabinet at 110-130 C. [0038] Gross yield: 162.5 g (yield 97.1% weight) of a white powder with a nonanoyloxybenzenesulfonate sodium (NOBS) content of 98%. Net yield of pure NOBS: 95.2% by weight.
94.9%	With 3,6,9-trioxaundecane; In isopar G; at 80 - 130℃; for 2.5h;	98.1 g (0.5 mol) of dried phenolsulfonate sodium, prepared according to Example 1b, were introduced into 143 g of ISOPAR G and heated to 130 C. 7 g of diethyleneglycol-diethylether were added. 114.8 g (0.65 mol) of nonanoyl chloride were then added dropwise over the course of 30 min, and the mixture was after-stirred at 130 C. The HCl gas which formed during the reaction was withdrawn. The reaction mixture was cooled after 2 h to 80 C. and filtered through a filter. The white reaction product was then washed twice with a small amount of ISOPAR G and then dried overnight in a drying cabinet at 110-130 C. Gross yield: 161.8 g (yield 96.2% weight) of a white powder with a nonanoyloxybenzenesulfonate sodium (NOBS) content of 98.7%. Net yield of pure NOBS: 94.9% by weight.
45 - 96%	In isopar G; at 80 - 130℃; for 2.5h;	98.1 g (0.5 mol) of dried phenolsulfonate sodium, prepared according to Example 1, were introduced into 150 g of ISOPAR G and heated to 120 C. 114.8 g (0.65 mol) of nonanoyl chloride were added dropwise over the course of 30 min, and the mixture was after-stirred at 130 C. The HCl gas which formed during the reaction was withdrawn. The reaction mixture was cooled after 2 h to 80 C. and filtered through a filter. The white reaction product was then washed twice with a small amount of ISOPAR G and then dried overnight in a drying cabinet at 110-130 C. Gross yield: 164.8 g (yield 98% weight) of a white powder with a nonanoyloxybenzenesulfonate sodium (NOBS) content of 98%. Net yield of pure NOBS: 96% by weight. Comparative Example B [0033] Use of overdried SPS, according to Example 1b [0034] 98.1 g (0.5 mol) of dried phenolsulfonate sodium, prepared according to Example 2, were introduced into 150 g of ISOPAR G and heated to 120 C. 114.8 g (0.65 mol) of nonanoyl chloride were then added dropwise over the course of 30 min, and the mixture was after-stirred at 120 C. The HCl gas which formed during the reaction was withdrawn. The reaction mixture was cooled after 2 h to 80 C. and filtered through a filter. The gray reaction product was then washed twice with a small amount of ISOPAR G and then dried overnight in a drying cabinet at 110-130 C. Gross yield: 129.5 g (yield 77% weight) of a beige-brown powder with a nonanoyloxybenzenesulfonate sodium (NOBS) content of 59%. Net yield of pure NOBS: 45% by weight.

Reference： [1]Patent: US2004/116725,2004,A1 .Location in patent: Page 3-4
[2]Patent: US2004/116725,2004,A1 .Location in patent: Page 3-4
[3]Patent: US2004/116725,2004,A1 .Location in patent: Page 3

34
[ 764-85-2 ]
1-(5-(pyridin-2-yl)oxazol-2-yl)nonan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%		A solution of 2-(oxazol-5-yl)pyridine (117 mg, 0.80 mmol) in anhydrous THF (5 mL) cooled to -75 C. under N2 was treated with n-BuLi (2.5 M in hexanes, 1.1 equiv, 0.88 mmol, 0.35 mL), and stirred for 20 min. ZnCl2 (0.5 M in THF, 2.0 equiv, 1.60 mmol, 3.2 mL) was added at -75 C., and stirred for 45 min at 0 C. Cul (1.0 equiv, 0.80 mmol, 152 mg) was added, and the solution was stirred for 10 min at 0 C. A separate flask was charged with nonanoic acid (2 equiv, 1.60 mmol, 253 mg, 0.28 mL) in anhydrous CH2Cl2 (4.2 mL), and to this solution cooled to 0 C. under N2 was added oxalyl chloride (5 equiv, 8.0 mmol, 1.02 g, 0.70 mL). After stirring at rt for 2 h, the solution was concentrated under reduced pressure and dissolved in anhydrous THF (1.5 mL). The solution of nonanoyl chloride was added and the solution was stirred for 1 h at 0 C. The reaction was diluted with EtOAc (10 mL), and washed with 15% aqueous NH4OH (1×10 mL), H2O (1×10 mL), and saturated aqueous NaCl (1×10 mL). The organic layer was dried (Na2SO4), filtered, and concentrated under reduced pressure. Flash chromatography (SiO2, 2.5 cm×17.5 cm, 20% EtOAc-hexanes) afforded 1-(5-(pyridin-2-yl)oxazol-2-yl)nonan-1-one (188) (94 mg, 0.33 mmol, 41% yield) as a light brown powder: mp 56-57 C.; 1H NMR (CDCl3, 250 MHz) d 8.61 (br d, J=4.4 Hz, 1H), 7.84-7.71 (m, 3H), 7.29-7.22 (m, 1H), 3.05 (t, J=7.3 Hz, 2H), 1.79-1.66 (m, 2H), 1.42-1.16 (m, 10H), 0.88-0.77 (m, 3H); 13C NMR (CDCl3, 62.5 MHz) d 188.4, 157.3, 153.1, 150.0, 146.2, 137.0, 126.8, 124.0, 120.3, 39.0, 31.7, 29.2, 29.0, 24.0, 23.9, 22.5, 14.0; IR (KBr) umax 2922, 2856, 1705, 1697, 1600, 1420, 1381 cm-1; MALDI-FTMS (DHB) m/z 287.1744 (C17H22N2O2+H+ requires 287.1754).

Reference： [1]Patent: US2006/111359,2006,A1 .Location in patent: Page/Page column 9

35
[ 764-85-2 ]
[ 2687-94-7 ]
[ 181213-09-2 ]

Yield	Reaction Conditions	Operation in experiment
		Example 2 Addition of NOP 98.1 g (0.5 mol) of dried phenolsulfonate sodium, prepared according to Example 1b, were introduced into 150 g of ISOPAR G and heated to 120 C. 0.7 g (3.7 mmol) of N-octylpyrrolidone were added. 114.8 g (0.65 mol) of nonanoyl chloride were then added dropwise over the course of 30 min, and the mixture was after-stirred at 120 C. The HCl gas which formed during the reaction was withdrawn. The reaction mixture was cooled after 2 h to 80 C. and filtered through a filter. The white reaction product was then washed twice with a small amount of ISOPAR G and then dried overnight in a drying cabinet at 110-130 C. Tel quel yield: 165.6 g (yield 98.4%) of a white powder with a nonanoyloxybenzenesulfonate sodium (NOBS) content of 97%. Yield of NOBS: 95%. The mother liquor could be used for the subsequent batch without further purification.

Reference： [1]Patent: US2003/64906,2003,A1

36
[ 764-85-2 ]
[ 115-95-7 ]
3,7-dimethyl-1,6-octadien-3-yl 3-(nonanyl)-3-oxo-propionate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With lithium diisopropyl amide In tetrahydrofuran; water	10 Preparation of 3,7-dimethyl-1,6-octadien-3-yl 3-(nonanyl)-3-oxo-propionate EXAMPLE 10 Preparation of 3,7-dimethyl-1,6-octadien-3-yl 3-(nonanyl)-3-oxo-propionate Lithium diisopropylamide (133.7 mL of a 2.0 M solution, 0.267 mol) is placed into a 500 mL three-necked round-bottomed flask fitted with a magnetic stirrer, internal thermometer, argon inlet, and addition funnel. The flask is cooled to -78° C. 3,7-dimethyl-1,6-octadien-3-yl acetate (24.73 g, 0.126 mol) is dissolved in THF (40 mL) and the resulting solution added to the flask over 45 min. Once addition is complete, the mixture is stirred for an additional 15 min. before being treated with a solution of nonanoyl chloride (21.88 g, 0.1 19 mol) over 30 min. The mixture is warmed to -20° C. and stirred at that temperature for 18 h. After warming to 0° C., the mixture is quenched with 20% HCl (60 mL). The mixture is poured into a separatory funnel containing ether (150 mL) and water (250 mL). The aqueous layer is extracted with ether (150 mL). The combined organic layers are washed with saturated NaHCO3 solution (2100 mL), water (2150 mL) and brine (150 mL), dried over MgSO4 and filtered. The solvent is removed by rotary evaporation to give an orange/red oil. The oil is purified by column chromatography (elution with 2% ethyl acetate/petroleum ether) to yield a colorless oil having 1 H and 13 C NMR spectra consistent with the desired product.

Reference： [1]Current Patent Assignee: PROCTER & GAMBLE CO - US6100233, 2000, A

37
[ 462-06-6 ]
[ 764-85-2 ]
[ 107-06-2 ]
4-n-Nonanoylbenzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With hydrogenchloride; sodium carbonate;aluminium trichloride; In water; dimethyl sulfoxide;	Synthesis of 4-nonanoyl benzoic acid 188.7 g (1.413 mol) of anhydrous aluminum chloride was added to 566 ml of 1,2-dichloro ethane, to which was added dropwise 161.5 g (1.682 mol) of benzene fluoride while holding temperature at 3-5 C. The resulting mixture was added with 254.5 g (1.442 mol) of nonanoyl chloride over 2 hours and then reacted at 8 C. for 1 hour and at 8-30 C. for 5 hours. The reaction solution was poured into 600 ml of concentrated hydrochloric acid containing 200 g of ice and extracted with 1.5 l of chloroform. The extract was washed with water and a 5% solution of sodium carbonate and dried on magnesium sulfate. After the solvent was distilled off, the residue was distilled under a reduced pressure (145-150 C./5 mmHg) to obtain 292.2 g (yield: 86%) of 4-nonanoyl-benzene fluoride. To 1350 ml of dimethylsulfoxide were added 292.2 g (1.238 mol) of the above 4-nonanoyl-benzene fluoride and 67.4 g (1.374 mol) of sodium cyanide, which were reacted at 110-125 C. for 12 hours. After the cooling up to room temperature, the reaction solution was poured into 2.7 l of water and extracted with 2 l of chloroform. The extract was washed with a saturated saline solution and dried on anhydrous magnesium sulfate. The solvent was distilled off to obtain 317.9 g (yield: 100%) of brown oily substance of 4-nonanoyl benzonitrile having an infrared absorption spectrum of 1680 cm-1.

Reference： [1]Patent: US5098602,1992,A

38
[ 764-85-2 ]
[ 3964-58-7 ]
3-chloro-4-octylcarbonyloxy benzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; hydrogenchloride; In dichloromethane; water;	Synthesis of 3-chloro-4-octylcarbonyloxy benzoic acid To a solution of 2.0 g (1.110-2 mol) of <strong>[3964-58-7]3-chloro-4-hydroxy benzoic acid</strong> in 40 ml of dried methylene chloride containing 3.0 g (9.210-3 mol) of pyridine was added dropwise 3.0 g (9.2*10-3 mol) of nonanoic acid chloride, which were stirred under reflux for 7 hours. After the completion of the reaction, the solution was washed with an aqueous solution of 1 normal hydrochloric acid and further with water and dried on anhydrous magnesium sulfate. After magnesium sulfate was filtered off, the resulting product was purified through a silica gel column chromatography using methylene chloride and ethanol at 9:1 (v/v) as a developing solution and then recrystallized with 5 ml of ethanol to obtain 750 mg (yield: 25%) of a white solid.
	With pyridine; In tetrachloromethane; water;	EXAMPLE 25 Preparation and properties of (2s,3s)-4'-(4'-(2-chloro-3-methylpentyloxycarbonyl)phenyl)phenyl-3-chloro-4-octylcarbonyloxybenzoic acid ester (AD) Four point five grams of <strong>[3964-58-7]3-chloro-4-hydroxybenzoic acid</strong> were dispersed in a mixed solvent of 30 ml of carbon tetrachloride and 5 ml of pyridine and then heated. 3.7 g of nonanic acid chloride was dropped into the mixture with refluxing. After heating 3 hours the solvent was removed from the mixture. After decomposing unreacted nonanic acid chloride by adding a small amount of water, the residue was washed with methanol to obtain 3-chloro-4-octylcarbonyloxybenzoic acid (AE).

Reference： [1]Patent: US5098602,1992,A
[2]Patent: EP191600,1991,B1

39
[ 764-85-2 ]
[ 56-40-6 ]
[ 79251-60-8 ]

Yield	Reaction Conditions	Operation in experiment
79.5%	sodium hydroxide; In water; ethyl acetate;	A. N-Nonanoyl glycine Glycine (20 mmol) was reacted with nonanoyl chloride (22 ml) in the presence of NaOH (40 mmol) in a mixture of water and ether as described in Example 1 Part A. The crude crystalline product (4.25 g) was recrytallized from ethyl acetate (40-50 ml) to give the title compound (3.42 g, 79.5%), m.p. 106-109 C.
79.5%	sodium hydroxide; In water;	A. N-Nonanoyl glycine Glycine (20 mmol) was reacted with nonanoyl chloride (22 ml) in the presence of NaOH (40 mmol) in a mixture of water and ether as described in Example 1 Part A. The crude crystalline product (4.25 g) was recrystallized from ethyl acetate (40-50 ml) to give the title compound (3.42 g, 79.5%), m.p. 106-109 C.

Reference： [1]Journal of Natural Products,2019,vol. 82,p. 1045 - 1048
[2]Patent: US4663336,1987,A
[3]Patent: US4734424,1988,A

40
[ 764-85-2 ]
[ 99-96-7 ]
[ 35179-36-3 ]

Yield	Reaction Conditions	Operation in experiment
92%		138.1 g (1.0 mol) of para-hydroxybenzoic acid were first dissolved in 500 ml of water and 500 ml of isopropanol and this solution was admixed at 0 to 5 C. with 230.0 g of KOH solution (50% strength by weight aqueous solution, 2.05 mol). The resulting pH was 13.5. Metered into this solution over the course of one hour, then, at 0 to 5 C., were 176.6 g (1.0 mol) of nonanoyl chloride, and the batch was stirred for 30 minutes at 0 to 5 C. thereafter. At the end of the after-stirring, the pH of the reaction mixture was 9.0. The reaction mixture was subsequently adjusted to a pH of 8 at 0 to 5 C. using 25.0 g of HCl solution (32% strength by weight aqueous solution), and the complete solution was heated to 55 to 60 C. and then adjusted to a pH of 1.5 to 3 using 100 g of HCl solution (32% strength by weight aqueous solution). The reaction mixture was cooled to 20 to 25 C. and the solid was filtered off on a suction filter and washed ten times with 150 ml of water. The yield after drying under reduced pressure at 100 C. was 255.95 g (92.0% of theory). According to HPLC and NMR measurement, the product was free from nonanoic acid and from unreacted para-hydroxybenzoic acid. The purity of the product is >99.9% by weight.
87.2%	With sodium hydroxide; In water; isopropyl alcohol; at 20 - 25℃; for 4h;pH 10.5;	Example 5 Synthesis of Para-Nonanoyloxybenzoic Acid (NOBA) 69.1 g (0.5 mol) of para-hydroxybenzoic acid were first dissolved in 200 ml of water and 300 ml of isopropanol and this solution was adjusted to a pH of 10.5 at 20 to 25 C. using 87.4 g of NaOH solution (32% strength by weight aqueous solution, 0.7 mol). Metered into this solution then at a pH of 10.5, over the course of three hours, were 88.3 g (0.5 mol) of nonanoyl chloride. The pH was held at 10.5 using 40.5 g of NaOH solution (32% strength by weight aqueous solution, 0.324 mol), and the temperature was held at 20 to 25 C. The batch was stirred for one hour thereafter. Subsequently the reaction mixture was adjusted to a pH of 7 at 20 to 25 C. using 5.3 g of HCl solution (32% strength by weight aqueous solution) and adjusted to a pH of 1.5 to 3 at 65 to 70 C. using 60 g of HCl solution (32% strength by weight aqueous solution). The reaction mixture was cooled to room temperature (25 C.) and the solid was filtered off on a suction filter and washed ten times with 150 ml of water. The yield after drying under reduced pressure at 100 C. was 121.3 g (87.2% of theory). According to HPLC and NMR measurement, the product was free from nonanoic acid and from unreacted para-hydroxybenzoic acid. The purity of the product is >99.9% by weight.
	With pyridine; In tetrachloromethane; water;	Four point five grams of 4-hydroxy benzoic acid were dissolved with a mixed solvent of 5 ml pyridine and 30 ml of carbon tetrachloride. 3.7 g of nonanic acid chloride was dropped into the mixture solution with refluxing for three hours, a small amount of water was added to the residue removed the solvent from the refluxing solution to decompose unreacted nonanic chloride. Then 4-octylcarbonyloxy benzoic acid (C) was obtained after washing methanol.

Reference： [1]Patent: US2013/217911,2013,A1 .Location in patent: Paragraph 0070
[2]Patent: US2013/211131,2013,A1 .Location in patent: Paragraph 0058
[3]Patent: EP191600,1991,B1

41
[ 764-85-2 ]
C₃₆H₅₂O₄₀S₄^(6-)*6Na⁽¹⁺⁾ [ No CAS ]
methyl O-(2,3,4-tri-O-nonanoyl-6-O-sulfo-α-D-glucopyranosyl)-1,4-O-(5-C-ethyl-3-O-methyl-2-O-nonanoyl-β-D-glucopyranosyluronic acid)-1,4-O-(6-O-nonanoyl-2,3-di-O-sulfo-α-D-glucopyranosyl)-1,4-O-(2,6-anhydro-5-C-carboxy-3-O-methyl-β-D-mannopyranosyl)-1,4-3,6-di-O-nonanoyl-2-O-sulfo-α-D-glucopyranoside hexasodium salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With pyridine; In N,N-dimethyl-formamide; at 0 - 20℃; for 16h;	An acyl chloride (10 molar equivalents) was added to a solution of pentasaccharide (1 molar equivalent) in pyridine (70 L/mol) and DMF (70 L/mol) at 0 C. The mixture was stirred for 16 hours at room temperature and directly poured onto a Sephadex LH-20 column (20 L/mmol) equilibrated with CH2Cl2/methanol/water (50:50:1) to give the acylated product; Pentasaccharide 38 (10 mg, 7.2 mumol) was acylated with 2-nonanoyl chloride according to 'Method D: Acylation' to give pentasaccharide 40 (13.4 mg, 78%), which had the following properties: chemical shifts of the anomeric protons: 5.54, 5.52, 5.21, 4.86 and 4.72 ppm; and MS (ESI-): chemical mass=2370.87; experimental mass=2372.1.

Reference： [1]Patent: EP1908768,2008,A1 .Location in patent: Page/Page column 16; 18

42
[ 6066-82-6 ]
[ 764-85-2 ]
[ 104943-23-9 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In dichloromethane; acetonitrile at 4℃; for 2h;	75 Example 75 Synthesis of Compound (64)[00216] To a stirred solution of N-hydroxysuccmimide (84 mg, 0 73 mmol) and triethylamine (92 5μL, 0.66 mmol) m 1 3 mL acetomtϖle/0 5 dichloromethane under argon atmosphere at 4 0C was added nonanoyl chloride (117 mg,0.66 mmol) in 0 3 ml acetonitrile After 2 hours of stirring, the reaction was stopped and the triethylammomum chloride was allowed to settle and filtered to give a 0 3M solution of the N-hydroxysuccmimide active ester (2,5- dioxopyrrohdin-1-yl nonanoate). This 2,5-dioxopyrrolidm-l-yl nonanoate solution (0 5 mL, 0 15 mmol) was added to a solution of Compound (60) (80 mg, 0 052 mmol) in 1 mL of anhydrous DMF The mixture was stirred at room temperature overnight The mixture was precipitated by addition of 10 mL diethyl ether. It was filtered. The solid was purified by preparative TLC to afford 25 mg (29% yield) t-Boc protected Compound (64) LC-MS (ESI).1577.6 (M+ + 1- Boc) A solution of this compound in 2 mL of rrifluoroacetic acid (TFA)/dichloromethane (1/1) was stirred for about 1 hour at 0 0C, until the HPLC-MS analysis showed no starting material left The solvent was evaporated under reduced pressure at 0 0C . The residue was added some ether and filtered to give Compound (64) as a white solid as TFA salt (15 mg, 60% yield), LC-MS (ESI): 1577 6 (M+ + 1)

Reference： [1]Current Patent Assignee: BIOMARIN PHARMACEUTICAL INC - WO2008/140973, 2008, A1 Location in patent: Page/Page column 65

43
[ 764-85-2 ]
[ 1134-47-0 ]
[ 1073838-91-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 7983 - 7991

44
[ 764-85-2 ]
[ 4569-45-3 ]
[ 1097177-07-5 ]

Reference： [1]Chemical Communications,2008,p. 4951 - 4953

45
[ 764-85-2 ]
[ 623-65-4 ]
[ 28319-77-9 ]
1-O-nonanoyl-2-O-hexadecanoyl-sn-glycero-3-phosphocholine [ No CAS ]

Reference： [1]Journal of the American Oil Chemists' Society,2008,vol. 85,p. 1005 - 1011

46
[ 764-85-2 ]
[ 30018-16-7 ]
[ 869885-19-8 ]

Reference： [1]Organic and Biomolecular Chemistry,2010,vol. 8,p. 274 - 281

47
[ 764-85-2 ]
[ 16290-26-9 ]
[ 139446-83-6 ]

Yield	Reaction Conditions	Operation in experiment
30.3%		To a solution of 3, 4-dihydroxybenzylamine hydrobromide (1 mmol) in anhydrous W^N-dimethylformamide(DMF) (2 mL) was added N,N-diisopropylethylamine (DIPEA)(2 mmol) to liberate the amine. After stirring at room temperature for 10 min, nonanoyl chloride (1 mmol) was added. The solution was stirred at room temperature for 24 h. After the reaction, water (40 mL) was added to the solution. The reaction mixture was transferred to a separating funnel and extracted with dichloromethane, CH2Cl2 (3 chi 6 mL) . The organic extracts were concentrated under reduced pressure to give a crude JCOIl product. The crude JCOIl product was then purified by silica gel column chromatography (using hexane/ethyl acetate, 2:1 v/v, as eluent) or preparative HPLC (using the protocol set out in "Analytical Protocols" above) to give the final JCOIl product. Analogues JC040, JC048, JC049 and JC050 were prepared using the same procedure as JCOIl except that the nonanoyl chloride was replaced with decanoyl chloride for JC040, dodecanoyl chloride for JC048, undecanoyl chloride for JC049, and tetradecanoyl chloride for JC050.

Reference： [1]Patent: WO2010/144059,2010,A2 .Location in patent: Page/Page column 66; 69

48
[ 764-85-2 ]
[ 7149-10-2 ]
[ 2444-46-4 ]

Yield	Reaction Conditions	Operation in experiment
91.5%	With sodium hydrogencarbonate; In dichloromethane; water; at 20 - 42℃; for 2.5h;	1) Preparation of crude product mixture: 105 g of vanillinamine hydrochloride was added to a mixture consisting of 200 g of sodium hydrogencarbonate, 500 mL of dichloromethane and 600 mL of water, and the mixture was stirred well and the mixture was further heated at room temperature (Methylene chloride: volume: 146.4 mL) was added dropwise over 1 hour. After completion of the dropwise addition, the temperature was raised to 42 C and maintained at that temperature for 1.5 hours. To obtain a crude product mixture (1420 mL);(2) Crystallization purification: The crude product mixture was cooled to room temperature, first using 200 mL of 25%Hydrochloric acid solution was shaken and allowed to stand for separation. The organic phase was separated (about 750 mL), and 150 mL of a 20%Of the sodium hydroxide solution was shaken and the organic phase was washed and allowed to stand for separation. The organic phase was separated again750 mL), washed with 200 mL of water, and partitioned. After washing with water, the organic phase (about 750 mL)150 mL of methylene chloride was distilled off to give a concentrated organic phase (ca. 600 mL), which was added to the concentrated organic phase1080mL petroleum ether after cooling crystallization, cooling rate of 0.25 / min, crystallization termination temperature of aboutAt -10 & lt; 0 & gt; C, maintaining the crystallization termination temperature for at least 30 min, filtering at the crystallization termination temperature,Dried to obtain solid synthetic capsaicin 148.6g, the yield was 91.5%, by high performance liquid chromatography(HPLC) to determine the purity of 99.5%.

Reference： [1]Patent: ,2016, .Location in patent: Paragraph 0040; 0041; 0042
[2]Journal of Agricultural and Food Chemistry,2010,vol. 58,p. 3342 - 3349

49
[ 764-85-2 ]
[ 3575-31-3 ]

Reference： [1]Journal of Chemical Research,2011,vol. 35,p. 703 - 706

50
[ 764-85-2 ]
[ 64-17-5 ]
[ 123-29-5 ]

Reference： [1]Chinese Journal of Chemistry,2011,vol. 29,p. 2153 - 2156

51
[ 764-85-2 ]
[ 92-66-0 ]
[ 63619-58-9 ]

Yield	Reaction Conditions	Operation in experiment
85.24%	With aluminum (III) chloride; In dichloromethane; at 15℃; for 10.5h;Cooling with ice;	General procedure: Dichloromethane (500 ml) was added to Aluminium chloride (26.66 g, 199.7 mmol, 133.5 g/mol). The mixture was stirred and cooled to a 5 C in a salt/ice bath. Acetyl chloride (26.83 g, 343.97 mmol, 78 g/mol) was quickly added through a dropping funnel and cooled to - 3 C to give a transparent yellow solution. Solid 4-bromobiphenyl (40 g, 171.67 mmol, 233 g/mol) was added in small amounts and stirred, wait for ½ an hour then add more. The mixture was left stirring for ten hours with the temperature rising to 15 C. The mixture was poured into bucket of ice /37% HCl to destroy the aluminium chloride, then transferred to a separatory funnel and extracted into DCM. Then the mixture was washed twice with 200 ml of water to destroy HCl. Again it was washed with 10% NaOH and 200 ml of water. The collected DCM layer was dried over Magnesium Sulfate, the most of it filtered by gravity. The solvent was removed in vacuo and residue was re-crystallised through ethanol. Yield ( 40.11 g, 84.98%): M.P. 133.3 [5]; deltaH(400 MHz;CDCl3) 2.64 (3H,s,CH3),8.03 (2H, d, J 8.25),7.64 (2H,d,J 8.61), 7.59 (2H,d,J 8.80), 7.49 (2H, d, J 8.43); deltaC (100.5;CDCl3)26.67 (CHMe),127.03, 128.81, 129.01, 132.09, 136.12, 138.76, 144.49, 197.62 (CO)

Reference： [1]Journal of Molecular Liquids,2012,vol. 175,p. 72 - 84
[2]Journal of Molecular Liquids,2012,vol. 170,p. 11 - 19

52
[ 764-85-2 ]
[ 1198780-43-6 ]
[ 1394312-88-9 ]

Yield	Reaction Conditions	Operation in experiment
93%	With triethylamine; In tetrahydrofuran; at 20℃;	To the solution of ( 6S, 9S ) -N-benzyl-6- ( 4-hydroxybenzyl ) -2, 9-dimethyl-4 , 7-dioxo-8- (quinolin-8-ylmethyl) octahydro-lH- pyrazino [2, 1-c] [1, 2, 4] triazine-l-carboxamide 579 mg (1 mmol) in dry-THF 20 ml, nonanoyl chloride 0.541 ml (3 mmol) and then triethylamine 0.418 ml (3 mmol) were added and stirred at room temperature overnight. The reaction " mixture was diluted with ethyl acetate 100 ml and washed with water 100 ml, saturated sodium bicarbonate 100 ml, water 100 ml, and brine 100 ml. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified by Buchi silica gel column chromatography(hexane : ethyl acetate=9:l to 0:10) to obtain title compound 671.7 mg (93%) .

Reference： [1]Patent: WO2012/115286,2012,A1 .Location in patent: Page/Page column 147

53
[ 22876-16-0 ]
[ 764-85-2 ]
C₁₇H₂₃NO₃ [ No CAS ]

Reference： [1]Arzneimittel-Forschung/Drug Research,2012,vol. 62,p. 330 - 334

54
[ 58546-59-1 ]
[ 764-85-2 ]
C₃₂H₄₄O₉ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52.6%	With dmap; In dichloromethane; at 45℃; for 3h;	General procedure: A mixture of schisantherol A (2a) (30 mg, 0.069 mmol), a catalytic amount of 4-dimethylaminopyridine (DMAP) in dry DCM (5 mL) in a 25-mL round flask, and acyl chloride (ca. 0.1 mL) was stirred under reflux at 45 C for 3 h. The reaction solution was successively washed with sat. aqueous Na2CO3 solution, brine, then dried over MgSO4 and concentrated in vacuo. The crude product thus obtained was purified by CC on silica gel to give various esters 11-20 (petrolumn ether/ethyl acetate 8:2).

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 59,p. 265 - 273

55
[ 764-85-2 ]
[ 100-66-3 ]
[ 52754-68-4 ]

Yield	Reaction Conditions	Operation in experiment
72%	With copper(II) ferrite; In 1,2-dichloro-ethane; at 80℃; for 24h;	General procedure: The FC acylation of various benzenes with acid chlorides was carried out in the presence of magnetic nano CuFe2O4 (particle size = 50 nm) by using one of the reaction condition (A-D) given below. Condition A: Anisole/arene (1 mmol), acid chloride (1.2 mmol), nano CuFe2O4 (20 mol %), 1,2-DCE (2 mL), 80 C and 24 h. Condition B: Anisole/arene (1 mmol), acid chloride (1.2 mmol), nano CuFe2O4 (20 mol %), 1,2-DCE (2 mL), rt (35-38 C) and 18 h. Condition C: Neat reaction, anisole/arene (3.3 mmol), acid chloride (1.2 mmol), nano CuFe2O4 (20 mol %), rt (35-38 C) and 18 h. Condition D: Neat reaction, arene/anisole (3.3 mmol), acid chloride (1.2 mmol), nano CuFe2O4 (20 mol %), 80 C and 18 h.

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 1738 - 1742

56
[ 764-85-2 ]
[ 111-86-4 ]
N-octylnonanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With triethylamine; In dichloromethane; at 20℃;Inert atmosphere;	To an anhydrous CH2Cl2 (15 mL) solution of nonanoyl chloride (3.61 mL, 20 mmol) were added Et3N (3.3 mL, 24 mmol) and octylamine (3.31 mL, 20 mmol). The mixture was stirred at room temperature overnight under N2, and was quenched by adding a small portion of water (ca. <2 mL). The residue was dissolved into CH2Cl2 (100 mL), washed with H2O (100 mL), and extracted with CH2Cl2 (100 mL×2). The organic layer was dried over Na2SO4 and filtrated. Evaporation of the filtrate gave colorless solid, which was recrystallized from CH2Cl2/hexane giving 3i (2.42 g, 8.98 mmol, 45%)

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 2674 - 2678

57
[ 764-85-2 ]
[ 1196-28-7 ]
[ 1449231-22-4 ]

Yield	Reaction Conditions	Operation in experiment
82%	With triethylamine; In dichloromethane; at 0 - 20℃; for 2h;Inert atmosphere;	To a solution of 24 (2.0g, 13.0mmol) in CH2Cl2 (25mL) was added Et3N (2.17mL, 15.6mmol). The mixture was cooled to 0C followed by the addition of nonanoyl chloride (2.60mL, 14.3mmol) and stirred for 2h at room temperature. 0.1N HCl (10mL) was added to the reaction mixture and extracted with CH2Cl2 (3×20mL). The combined organic layers were washed with saturated aqueous NaHCO3 (30mL), and brine (30mL). The organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. The resultant crude residue was purified using column chromatography (EtOAc/n-hexane=1/10) to afford 27 (3.09g, 82%) as a colorless oil; IR (KBr) nu 3255, 2953, 2928, 1698, 754cm-1; HRMS (ESI) Anal. Calcdfor C18H27NNaO2 m/z 312.1934 [M+Na]+, found 312.1933; 1H NMR (400MHz, CDCl3) delta 11.76 (br s, 1H), 8.77 (dd, J=8.5, 1.1Hz, 1H), 7.93 (dd, J=8.0, 1.6Hz, 1H), 7.53 (ddd, J=8.5, 7.3, 1.6Hz, 1H), 7.09 (ddd, J=8.0, 7.3, 1.1Hz, 1H), 3.07 (q, J=7.3Hz, 2H), 2.43 (t, J=7.6Hz, 2H), 1.74 (m, 2H), 1.20-1.41 (m, 13H), 0.87 (t, J=6.6Hz, 3H); 13C NMR (100MHz, CDCl3) delta 205.4, 172.8, 141.1, 134.8, 130.6, 122.1, 121.4, 120.9, 38.8, 33.2, 31.9, 29.3, 29.2, 29.1, 25.6, 22.6, 14.1, 8.5.
	With triethylamine; In dichloromethane; at 20℃;Inert atmosphere;	In an argon atmosphere, the compound expressed by the above Structural Formula (14) (1 equivalent) was dissolved in methylene chloride, and triethylamine (2 equivalents) was added thereto. Furthermore, nonanoyl chloride (1.1 equivalents), which is an acid chloride, was added dropwise to the mixture in an ice bath, followed by stirring at room temperature. The reaction was terminated with 0.1N hydrochloric acid, and the mixture was extracted with methylene chloride, followed by washing with saturated sodium hydrogencarbonate aqueous solution and brine. The combined organic layer was dried with Glauber's salt, and then the solvent was evaporated. The residue was purified through silica gel chromatography (hexane:ethyl acetate), and as a result the compound expressed by Structural Formula (16) was obtained. (0449) -Physico-Chemical Properties- (0450) Physico-chemical properties of the compound expressed by Structural Formula (16) as follows. (1) Appearance: colorless oily substance (2) Molecular formula: C18H27O2N (3) High resolution mass spectrometry (HRESI-MS)(m/z): (0451) Found: 312.1933 (M+Na)+. (0452) Calcd: 312.1934 (as C18H27O2NNa). (4) Infrared absorption spectrum: (0453) Peaks of infrared absorption measured by the KBr tablet method are as follows. (0454) vmax(KBr)cm-1: 3255, 2953, 2928, 1698, 754 (5) Proton nuclear magnetic resonance spectrum (400 MHz, CDCl3): (0455) delta=0.87 (3H, t, J=6.6), 1.20-1.41 (13H, m), 1.74 (2H, m), 2.43 (2H, t, J=7.6), 3.08 (2H, q, J=7.3), 7.09 (1H, ddd, J=8.0, 7.3, 1.1), 7.53 (1H, ddd, J=8.5, 7.3, 1.6), 7.93 (1H, dd, J=8.0, 1.6), 8.77 (1H, dd, J=8.5, 1.1), 11.76 (1H, br s) (6) 13C nuclear magnetic resonance spectrum (100 MHz, CDCl3): (0456) delta=8.54, 14.07, 22.63, 25.55, 29.14, 29.22, 29.28, 31.87, 33.20, 38.80, 120.85, 121.96, 122.12, 130.57, 134.84, 141.08, 172.80, 205.37

Reference： [1]Tetrahedron,2013,vol. 69,p. 7608 - 7617
[2]Patent: US2016/9651,2016,A1 .Location in patent: Paragraph 0448-0456

58
[ 764-85-2 ]
3-(9H-fluoren-9-yl)pyrrolidine-2,5-dione [ No CAS ]
3-(9H-fluoren-9-yl)-1-nonanoyl-2,5-pyrrolidinedione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%		General procedure: A dispersion of NaH in mineral oil (0.4mmol) was added to a solution of amide 2 (0.2mmol) in THF under argon atmosphere. After 20min, the mixture was cooled to 4C and a solution of acyl chloride (0.3mmol) in THF was added. The reaction mixture was stirred for 4h at room temperature. After evaporation of solvent, the resulting residue was mixed with distilled water (30mL) and extracted 3 times with CH2Cl2 (3×20mL). The organic layer was dried over MgSO4 and then concentrated under reduced pressure. The product was further purified by flash chromatography.

Reference： [1]European Journal of Medicinal Chemistry,2013,vol. 70,p. 37 - 48

59
2-(3-fluoro-4-hydroxyphenyl)benzothiazole [ No CAS ]
[ 764-85-2 ]
[ 1564099-73-5 ]

Yield	Reaction Conditions	Operation in experiment
92%	With triethylamine; In dichloromethane; at 20℃; for 1h;	General procedure: A solution of octanoyl chloride (0.21 g, 1.32 mmol) in CH2Cl2 (10 mL) was added drop-wise to a stirred solution of compound 10a (0.30 g, 1.32 mmol) and Et3N (0.27 g, 2.64 mmol) in CH2Cl2 (10 mL). The mixture was allowed to stir (1 h) at room temperature. The mixture was neutralized by the addition of dilute aqueous HCl solution and then water (10mL) was added. The mixture was extracted with CH2Cl2 (2×10mL) and the combined organic extracts were dried (MgSO4) and evaporated yielding the crude product

Reference： [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 1250 - 1261

60
[ 764-85-2 ]
[ 6305-38-0 ]
C₁₃H₂₃NO₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	With sodium carbonate; In dichloromethane; water; at 20℃; for 2h;	General procedure: The appropriate acid chloride 2 (4 mmol) was added dropwise at room temperature to a vigorously stirred mixture of (S)-homoserine lactone hydrobromide (1, 1.3 equiv, 0.95 g,5.2 mmol) and Na2CO3 (2.6 equiv, 0.55 g, 10.4 mmol) in water(5 mL per mmol acid chloride) and CH2Cl2 (5 mL per mmol acid chloride). The mixture was stirred vigorously at room temperature for 2 h. CH2Cl2 was added, the aqueous and organic phases were separated and the aqueous phase was extracted with CH2Cl2 (2 × 20 mL). The combined organic extracts were washed with saturated aqueous NaHCO3(2 × 40 mL), dried (MgSO4), filtered and the solvent removed under reduced pressure to yield the desired product 3. The crude product was purified via column chromatography on silica gel(EtOAc/petroleum ether 4:1).

Reference： [1]Beilstein Journal of Organic Chemistry,2014,vol. 10,p. 2539 - 2549

61
[ 764-85-2 ]
[ 1516-08-1 ]
d5-ethyl nonanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With pyridine; dmap; In dichloromethane; at 0 - 20℃;Inert atmosphere;	To a stirred solution of d6-ethanol (500 muL, 8.64 mmol) in anhydrous CH2Cl2 (4 mL) under N2 at room temperature was added pyridine (614 muL, 7.59 mmol) followed by 4-dimethylaminopyridine (DMAP) (0.106 g, 0.868 mmol). After dissolution, nonanoyl chloride (1.50 mL, 8.32 mmol) was added drop-wise to the solution at 0 C, causing the formation of a white precipitate. Additional anhydrous CH2Cl2 (3 mL) was added and the solution was stirred overnight at room temperature, before being quenched with NaHCO3 (10 mL). The phases were separated, and the aqueous phase was extracted with CH2Cl2 (3 × 20 mL), and the combined organic phases were washed with brine (20 mL), dried (NaSO4),and filtered before being concentrated in vacuo to yield a yellow/brown oil. Purification by column chromatography on silica (85% hexane/EtOAc, Rf = 0.45) gave the title compound (1.41 g, 7.37 mmol, 89%) as a colorless oil (97% pure by GC-MS). 1H-NMR (600 MHz, CD3OD): delta 2.29 (2H, t, J = 7.6 Hz, H2); 1.62 (2H, app q, J = 7.4 Hz, H3); 1.35-1.22 (10 H, m, H4-8); 0.88 (3H, t, J = 7.0 Hz, H9); 13C-NMR (150 MHz, MeOH-d4): delta 173.97 (C1); 59.40 (JC-D = 22 Hz, CD2); 34.39 (C2); 31.79 (C7); 29.21 (C4); 29.13 (C5); 29.11 (C6); 24.97 (C3); 22.63 (C8); 14.09 (C9); 13.21 (JC-D = 19.4 Hz, CD3). ESI-HRMS (m/z): Calcd for C11H18D5O2+ ([M+H]+), 192.2006; found 192.2022. EI-MS (m/z) (%) 191 (M+, 3), 162 (12), 148 (13), 141 (19), 120 (6), 106 (39), 93 (100), 84 (6), 74 (28), 61 (20), 57 (13), 55 (17).

Reference： [1]Molecules,2015,vol. 20,p. 7845 - 7873

62
[ 764-85-2 ]
[ 461-05-2 ]
3-carboxy-2-(nonanoyloxy)-N,N,N-trimethylpropan-1-aminium [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With trifluoroacetic acid; at 50℃;	Carnitine derivatives were prepared based on the method of Bhmer and Bremer [44]. To a stirred solution of trifluoroacetic acid (TFA) (500 muL) at room temperature containing <strong>[461-05-2](±)-carnitine chloride</strong> (1.00 g, 5 mmol) was added dropwise nonanoyl chloride (1.77 g, 10 mmol), at which time a white precipitate formed. The reaction was maintained at 50 C with stirring overnight. After cooling to room temperature, acetone (5.5 mL) was added, stirring was maintained for 1 hour and the precipitate that formed was removed via centrifugation. Diethyl ether (~3 mL) was added dropwise to incipient cloudiness, followed by cooling to 0 C. Additional Et2O (10 mL) was added once crystallisation was well underway. Once crystallisation was complete, centrifugation and resuspension in Et2O (40 mL) was used to wash the crystals (repeated two more times), followed by isolation and drying. Purification by recrystallisation in MeOH/Et2O produced the known [45] title compound (1.16 g, 3.43 mmol, 69%) as a white crystalline solid, which was >99% pure (HPLC-MS), mp 155.2-157.7 C. 1H-NMR (MeOH-d4) delta 5.63 (1H, app q, J = 6.9 Hz); 4.92 (1H, bs); 3.49 (1H, dd, J = 14.4, 8.6 Hz); 3.75 (1H, dd, J = 14.4, 0.90 Hz); 3.23 (9H, s); 2.79-2.76 (2H, m); 2.39 (2H, m); 1.63 (2H, q, J = 7.35 Hz); 1.38-1.25 (10H, m); 0.90 (3H, t, J = 7.1 Hz). 13C-NMR (MeOH-d4) delta 174.27, 172.54, 69.50, 66.35, 54.68, 37.93, 35.22, 33.11, 30.50, 30.39, 30.31, 25.83, 23.84, 14.60.

Reference： [1]Molecules,2015,vol. 20,p. 7845 - 7873

63
[ 764-85-2 ]
[ 2174-64-3 ]
1-(2,6-dihydroxy-4-methoxyphenyl)nonan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With aluminum (III) chloride In dichloromethane at 20℃;
70 mg	Stage #1: 5-methoxyresorcinol With aluminum (III) chloride In dichloromethane for 0.25h; Stage #2: Nonanoyl chloride In dichloromethane for 3h;	Synthesis of 1-(2,6-Dihydroxy-4-methoxyphenyl)nonan-1-one Aluminum (III) chloride (95 mg, 0.714 mmol) was added toa solution of 5-methoxyresorcinol (50 mg, 0.357 mmol) in dichloromethane(2 mL) at room temperature. After 15 min, nonanylchloride (100 μL, 0.555 mmol) was added. The mixturewas stirred for 3 h, poured into water (20 mL), and extractedthree times with ethyl acetate (20 mL). The organic layer waswashed with saturated NaCl solution, dried over anhydroussodium sulfate, and evaporated to dryness. The residue waschromatographed over silica gel and eluted by hexane-ethylacetate (19 : 1) to give 1-(2,6-dihydroxy-4-methoxyphenyl)-nonan-1-one (70 mg, 0.250 mmol [yield, 70%]). The spectraldata of the eluate were identical to those reported previouslyfor 1-(2,6-dihydroxy-4-methoxyphenyl) nonan-1-one.21)

Reference： [1]Nguyen, Van Hai; Kikuchi, Haruhisa; Kubohara, Yuzuru; Takahashi, Katsunori; Katou, Yasuhiro; Oshima, Yoshiteru [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 15, p. 4311 - 4315]
[2]Takahashi, Katsunori; Kikuchi, Haruhisa; Nguyen, Van Hai; Oshima, Yoshiteru; Ishigaki, Hirotaka; Nakajima-Shimada, Junko; Kubohara, Yuzuru [Biological and Pharmaceutical Bulletin, 2017, vol. 40, # 11, p. 1941 - 1947]

64
[ 764-85-2 ]
[ 129604-54-2 ]
1-(4-(9H-fluoren-9-yl)piperazin-1-yl)nonan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With triethylamine; In dichloromethane; at 20℃;Cooling with ice;	General procedure: 1-(9H-Fluoren-9-yl)piperazine 3 (1.0 eq) was dissolved in dry dichloromethane. Triethylamine (1.2 eq) was added and the reaction mixture was stirred at room temperature for 10 min. Benzoyl chloride (1.1 eq) was slowly added to reaction mixture previously cooled with an ice bath. After complete addition the reaction mixture was stirred overnight at room temperature. A saturated aqueous solution of sodium hydrogenocarbonate was added and the product was extracted with dichloromethane (3). The organic phase was washed with a large amount of water, dried over magnesium sulfate, filtered and concentrated under vacuum pressure.The resulting crude product was purified by flash chromatography as indicated in each case to afford the desired compound. Reagents: 1-(9H-fluoren-9-yl)piperazine 3 (0.40 mmol, 100 mg), triethylamine (0.48 mmol, 65 muL) and nonanoyl chloride (0.48 mmol, 86 muL). The crude product was purified by flash chromatography (isocratic 80/20 petroleum ether/ethyl acetate) to afford a white solid (114 mg, 73%). TLC Rf: 0.62 (dichloromethane/methanol 95/5); mp: 88 C; IR (cm-1): 673, 740, 1001, 1137, 1196, 1228, 1320, 1448, 1639, 2818, 2851, 2919. HPLC: method 2, rt = 5.04 min, purity 95%. 1H NMR (300 MHz, CDCl3) delta (ppm): 0.90 (t, J = 7.2 Hz, 3H); 1.20-1.42 (m, 10H); 1.35-1.67 (m, 2H); 2.28 (t, J = 7.2 Hz, 2H); 2.49 (t, J = 4.8 Hz, 2H); 2.77 (t, J = 4.8 Hz, 2H); 3.41 (t, J = 4.8 Hz, 2H); 3.66 (t, J = 4.8 Hz, 2H); 4.90 (s, 1H); 7.32 (td, J = 1.5 Hz, 7.5 Hz, 2H); 7.41 (t, J = 7.5 Hz, 2H); 7.64 (d, J = 7.5 Hz, 2H); 7.72 (d, J = 7.2 Hz, 2H). 13C NMR (75 MHz, CDCl3) delta (ppm): 14.1 (CH3); 22.7 (CH2); 25.4 (CH2); 29.2 (CH2); 29.4 (CH2); 29.5 (CH2); 31.8 (CH2); 33.3 (CH2); 70.0 (CH); 119.8 (2 * CH); 125.9 (2 * CH); 127.1 (2 * CH); 128.3 (2 * CH); 141.1 (2 * C); 143.5 (2 * C); 171.7 (C). MS (DCI/CH4) m/z: 419.31 [M+C2H5+], 391.27 [M+H+], 165.07 [M-225]. HRMS (DCI/CH4): for C26H35N2O [M+H+]: calcd: 391.2749; found: 391.2751.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 101,p. 218 - 235

65
[ 764-85-2 ]
[ 37778-99-7 ]
(S)-2-phenylpropyl nonanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
188 mg	With dmap; triethylamine In dichloromethane at 0 - 20℃; for 1h; Inert atmosphere;

Reference： [1]Gaspa, Silvia; Porcheddu, Andrea; De Luca, Lidia [Organic Letters, 2015, vol. 17, # 15, p. 3666 - 3669]

66
[ 764-85-2 ]
[ 6645-46-1 ]
nonanoyl-L-carnitine [ No CAS ]

Reference： [1]Journal of Lipid Research,2015,vol. 56,p. 2029 - 2039

67
[ 764-85-2 ]
[ 481-39-0 ]
5-O-nonanoyloxy-1,4-naphthoquinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With dmap; In dichloromethane; at 0 - 20℃;	General procedure: These derivatives were obtained according to the methodology previously described by Mathew et al. (2010) with some modifications. These acylation reactions were performed in dichloromethane with juglone (50 mg, 1 eq.) as the starting material. 4-Dimethylaminopyridine (68.4 muL,3 eq.) and the corresponding acyl chloride (125 muL, 5 eq.) were added at 0 C. The reaction mixture was stirred at roomtemperature and monitored by TLC. After completion of thereaction, the organic phase was washed with brine, driedover anhydrous Na2SO4 and concentrated under vacuum.The resulting mixture was purified by column chromatographyusing 100 % chloroform as eluent to obtain compounds 5-15. New compounds are characterized.

Reference： [1]Medicinal Chemistry Research,2016,vol. 25,p. 1274 - 1285

68
[ 764-85-2 ]
C₂₆H₃₄Br₂ [ No CAS ]
C₃₅H₅₀Br₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%		Monomer1 stage4 (131 g, 0.258 mol) was dissolved under nitrogen in diethyl ether (2 L) and n-butyl lithium (2M in hexanes, 109 mL, 0.27 mol) was added drop-wise keeping the internal temperature below 30 C. Once the addition was completed, the dark red mixture was stirred at room temperature for 10 min and then cannulated into a flask containing nonylchloride (50.2 g, 0.28 mol). The resulting mixture was stirred for 1 h at room temperature after which full conversion was achieved monitored by GCMS. The reaction was quenched with water (500 mL), and stirred at room temperature for 20 min. The organic layer was separated, and the aqueous layer was extracted twice with diethyl ether. The combined organic phases were washed with a saturated solution sodium hydrogencarbonate, dried over MgSO4. And concentrated to give a yellow oil, which was Monomer1 stage5 characterised by GCMS and 1H-NMR (160 g, 91% yield). This material was used in the next step without any further purification.

Reference： [1]Patent: US2016/190458,2016,A1 .Location in patent: Paragraph 0198

69
[ 764-85-2 ]
2,6-difluoro-3-aminobenzamide [ No CAS ]
2,6-difluoro-3-(nonannoylamido)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	With pyridine; In dichloromethane; at 0℃; for 4h;	The 2,6-difluoro-3-aminobenzamide (0.17g, 1 . 0mmol), dichloromethane (DCM) (5 ml), pyridine (5 ml) in the 0 C uniformly mixed under stirring, PV drops (nonanoylchloride) enters the pelargonyl chloride (0.23g, 1 . 3mmol), the reaction mixture at 0 C mixing and stirring under 4 hours. The reaction mix is provided with a inlet fluid but actually 1MHCl (50 ml) in a separatory funnel, the chemical reaction quenching, with dichloromethane (DCM) (20mLx3) extraction. With sodium bicarbonate (NaHCO 3) to the mixed organic layer to be cleaned, of magnesium sulfate (MgSO 4) drying, filtration and evaporating solvent under reduced pressure, to obtain crude reactant, for rapid column chromatography, the obtained compound (0.11g) to yield of 36%
36%	With pyridine; In dichloromethane; at 0℃; for 4h;	To a well-stirred solution of 2,6-difluoro-3-aminobenzamide(10) (0.17 g, 1.0 mmol) in DCM (5 mL) and pyridine (5 mL) at 0 C,was added nonanoyl chloride (0.23 g, 1.3 mmol) dropwise. The reactionmixture was stirred for 4 h at 0 C. The reaction was thenquenched by pouring into a separating funnel containing 1M HCl(50 mL) and extracted with DCM (20 mL x 3). The combined organiclayers was washed with NaHCO3, dried over MgSO4, filtered andevaporated under reduced pressure to give a crude reactionmixture, which was further subjected to purification by flash columnchromatography on silica gel with gradient elution (10%-40%ethyl acetate in hexane) to afford the desired compound (0.11 g,36%). 1H NMR (400 MHz, Acetone-d6) delta 8.95 (br. s., 1H), 8.14-8.19(m, 1H), 7.51 (br. s., 1H), 7.19 (br. s., 1H), 7.02 (dd, J 8.0, 8.0 Hz, 1H),2.47 (t, J 7.2 Hz, 2H), 1.66-1.74 (m, 2H), 1.25e1.43 (m, 10H),0.81-0.98 (m, 3H); 13C NMR (101 MHz, Acetone-d6) delta 171.7, 161.2 (s,CONH2), 151.8 (dd, JCF 234, 8.2 Hz, C6), 146.0 (dd, JCF 245, 8.2 Hz,C2), 134.1 (dd, JCF 14, 2.7 Hz, C3), 123.6 (dd, JCF 9.1, 5.5 Hz, C4),116.8 (dd, JCF 23, 23 Hz, C1), 110.7 (dd, JCF 21, 3.6 Hz, C5), 36.3,31.7, 28.4, 25.3, 22.4, 19.1, 18.5, 13.4; LRMS (ESI) m/z 313 (M H,100); HRMS (ESI) calcd for C16H22N2O2F6 (M H) 313.1728, found313.1726.

Reference： [1]Patent: CN105461585,2016,A .Location in patent: Paragraph 0159-0160
[2]European Journal of Medicinal Chemistry,2019,vol. 163,p. 95 - 115

70
[ 625-82-1 ]
[ 764-85-2 ]
[ 109-63-7 ]
C₂₁H₃₁BF₂N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%		A 1L round bottom flask under a nitrogen atmosphere charged with 2,4-dimethyl-pyrrole 15.0 g (158 mmol), n-octyl chloride 14.0 g (79mmol) and dichloromethane (DCM) 450 ml were added and stirred at room temperature for 24 hours. Then, triethylamine (TEA) 55 ml, boron trifluoride diethyl ether (BF3OEt2) 55 ml was added and stirred for 4 hours at room temperature. Subsequently, by introducing water and the layers were separated and the organic layer was concentrated and then a mixed solvent of dichloromethane and hexane (1: 2 (v / v)) by performing column chromatography to give a red solid of intermediate (2) 9.4 g (yield: 45%).

Reference： [1]Patent: KR2015/131807,2015,A .Location in patent: Paragraph 0087-0090
[2]Chemical Communications,2018,vol. 54,p. 9123 - 9126

71
[ 764-85-2 ]
[ 136-64-1 ]
C₂₆H₄₂N₄O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23.7 g	With pyridine; In 1,4-dioxane;Inert atmosphere;	Under a nitrogen atmosphere, 1, 4-dioxane 200 ml of compound (i) dissolved in 10g, polypyridine 24. 4g (309mmol) is applied, then the nonanoyl diazidosulfochloride 21. 8g (123. 6mmmol) is added to a stirred replicated. After that, the reaction solution is poured into water, a solid sucking and filtering separated by filtration, washed several times after the filter is distilled water, dried under reduced pressure, 23. 7g compd. (j) is obtained.

Reference： [1]Patent: JP5664479,2015,B2 .Location in patent: Paragraph 0183-0184; 0186

72
[ 764-85-2 ]
C₄₈H₉₆N₂O₄ [ No CAS ]
C₅₇H₁₁₂N₂O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With dmap; triethylamine; In benzene; at 20℃; for 0.166667h;	A solution of nonanoyl chloride (1.3 eq., 1.27 mmol, 225 mg) in benzene(10 mL) was added via syringe to a solution of the compound 9b from step 1(0.75 g, 0.98mmol) and triethylamine (5 eq, 4.90 mmol, 0.68 mL) and DMAP (20 mg) in benzene (10mL) at RT in 10 mm. After addition, the mixture was stirred at RT overnight. Methanol(5.5 mL) was added to remove excess acyl chloride. After 3 h, the mixture was filteredthrough a pad of silica gel (1.2 cm). Concentration gave a colorless oil (0.70 g). The crude product (0.70 g) was purified by flash dry columnchromatography on silica gel (0 to 4% MeOH in chloroform). This yielded 457 mg of colorless oil, 0.50 mmol, 51%. 1HNIVIR (400 IVIFIz, CDC13) : 4.54-4.36 (very br.,estimated 0.3H, due to slow isomerization about amide bond), 3.977, 3.973 (two sets of doublets, 5.8 Hz, 4H), 3.63 (quintet-like, 6.8 Hz, 0.7H), 3.14-3.09 (m, 2H), 2.33-2.25 (m, 8H), 2.23, 2.22 (two sets of singlet, 6H), 1.76-1.56 (m, 1OH), 1.49-1.39 (m, 4H), 1.37-1.11 (62H), 0.92-0.86 (m, 15H).
51%	With dmap; triethylamine; In benzene; at 20℃;	A solution of nonanoyl chloride (1.3 eq., 1.27 mmol, 225 mg) in benzene (10 mL) was added via syringe to a solution of the compound 9b from step 1(0.75 g, 0.98 mmol) and triethylamine (5 eq, 4.90 mmol, 0.68 mL) and DMAP (20 mg) in benzene (10 mL) at RT in 10 min. After addition, the mixture was stirred at RT overnight. Methanol (5.5 mL) was added to remove excess acyl chloride. After 3 h, the mixture was filtered through a pad of silica gel (1.2 cm). Concentration gave a colorless oil (0.70 g). (0196) The crude product (0.70 g) was purified by flash dry column chromatography on silica gel (0 to 4% MeOH in chloroform). This yielded 457 mg of colorless oil, 0.50 mmol, 51%. 1HNMR (400 MHz, CDCl3) delta: 4.54-4.36 (very br., estimated 0.3H, due to slow isomerization about amide bond), 3.977, 3.973 (two sets of doublets, 5.8 Hz, 4H), 3.63 (quintet-like, 6.8 Hz, 0.7H), 3.14-3.09 (m, 2H), 2.33-2.25 (m, 8H), 2.23, 2.22 (two sets of singlet, 6H), 1.76-1.56 (m, 10H), 1.49-1.39 (m, 4H), 1.37-1.11 (62H), 0.92-0.86 (m, 15H).
51%	With dmap; triethylamine; In benzene; at 20℃;	A solution of nonanoyl chloride (1.3 eq., 1.27 mmol, 225 mg) in benzene (10 mL) was added via syringe to a solution of the compound 9b from step 1(0.75 g, 0.98 mmol) and triethylamine (5 eq, 4.90 mmol, 0.68 mL) and DMAP (20 mg) in benzene (10 mL) at RT in 10 min. After addition, the mixture was stirred at RT overnight. Methanol (5.5 mL) was added to remove excess acyl chloride. After 3 h, the mixture was filtered through a pad of silica gel (1.2 cm). Concentration gave a colorless oil (0.70 g). (0892) [0448] The crude product (0.70 g) was purified by flash dry column chromatography on silica gel (0 to 4% MeOH in chloroform). This yielded 457 mg of colorless oil, 0.50 mmol, 51%. lHNMR (400 MHz, CDC13) delta: 4.54-4.36 (very br., estimated 0.3H, due to slow isomerization about amide bond), 3.977, 3.973 (two sets of doublets, 5.8 Hz, 4H), 3.63 (quintet-like, 6.8 Hz, 0.7H), 3.14-3.09 (m, 2H), 2.33- 2.25 (m, 8H), 2.23, 2.22 (two sets of singlet, 6H), 1.76-1.56 (m, 10H), 1.49-1.39 (m, 4H), 1.37-1.11 (62H), 0.92-0.86 (m, 15H).

51%	With dmap; triethylamine; In benzene; at 20℃;	A solution of nonanoyl chloride (1.3 eq, 1.27 mmol, 225 mg) in benzene (10 mL) was added via syringe to a solution of the compound 9b from step 1(0.75 g, 0.98 mmol) and triethylamine (5 eq, 4.90 mmol, 0.68 mL) and DMAP (20 mg) in benzene (10 mL) at RT in 10 min. After addition, the mixture was stirred at RT overnight. Methanol (5.5 mL) was added to remove excess acyl chloride. After 3 h, the mixture was filtered through a pad of silica gel (1.2 cm). Concentration gave a colorless oil (0.70 g). (0716) The crude product (0.70 g) was purified by flash dry column chromatography on silica gel (0 to 4% MeOH in chloroform). This yielded 457 mg of colorless oil, 0.50 mmol, 51%. 1H MR (400 MHz, CDC13) delta: 4.54-4.36 (very br., estimated 0.3H, due to slow isomerization about amide bond), 3.977, 3.973 (two sets of doublets, 5.8 Hz, 4H), 3.63 (quintet-like, 6.8 Hz, 0.7H), 3.14-3.09 (m, 2H), 2.33-2.25 (m, 8H), 2.23, 2.22 (two sets of singlet, 6H), 1.76-1.56 (m, 10H), 1.49-1.39 (m, 4H), 1.37-1.11 (62H), 0.92-0.86 (m, 15H).
457 mg	With dmap; triethylamine; In benzene; at 20℃;	A solution of nonanoyl chloride (1.3 eq, 1.27 mmol, 225 mg) in benzene (10 mL) was added via syringe to a solution of the compound 9b from step 1(0.75 g, 0.98 mmol) and triethylamine (5 eq, 4.90 mmol, 0.68 mL) and DMAP (20 mg) in benzene (10 mL) at RT in 10 min. After addition, the mixture was stirred at RT overnight. Methanol (5.5 mL) was added to remove excess acyl chloride. After 3 h, the mixture was filtered through a pad of silica gel (1.2 cm). Concentration gave a colorless oil (0.70 g). (0780) The crude product (0.70 g) was purified by flash dry column chromatography on silica gel (0 to 4% MeOH in chloroform). This yielded 457 mg of colorless oil, 0.50 mmol, 51%. 1H NMR (400 MHz, CDCl3) delta: 4.54-4.36 (very br., estimated 0.3H, due to slow isomerization about amide bond), 3.977, 3.973 (two sets of doublets, 5.8 Hz, 4H), 3.63 (quintet-like, 6.8 Hz, 0.7H), 3.14-3.09 (m, 2H), 2.33-2.25 (m, 8H), 2.23, 2.22 (two sets of singlet, 6H), 1.76-1.56 (m, 10H), 1.49-1.39 (m, 4H), 1.37-1.11 (62H), 0.92-0.86 (m, 15H).

Reference： [1]Patent: WO2016/176330,2016,A1 .Location in patent: Page/Page column 141
[2]Patent: US2016/376224,2016,A1 .Location in patent: Paragraph 0195; 0196
[3]Patent: WO2018/107026,2018,A1 .Location in patent: Paragraph 0447; 0448
[4]Patent: WO2018/191719,2018,A1 .Location in patent: Page/Page column 133
[5]Patent: WO2018/81480,2018,A1 .Location in patent: Page/Page column 127

73
[ 764-85-2 ]
[ 767-64-6 ]
N-(benzo[c][1,2,5]thiadiazol-4-yl)nonanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	Stage #1: Nonanoyl chloride; 4-Amino-2,1,3-benzothiadiazole With triethylamine Inert atmosphere; Stage #2: Nonanoyl chloride In dichloromethane at 20℃; for 12h; Inert atmosphere;

Reference： [1]Reddy, Chennakesava; Bisht, Narendra; Parella, Ramarao; Babu, Srinivasarao Arulananda [Journal of Organic Chemistry, 2016, vol. 81, # 24, p. 12143 - 12168]

74
[ 764-85-2 ]
C₅₀H₁₀₀N₂O₄ [ No CAS ]
C₅₉H₁₁₆N₂O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With dmap; triethylamine; In benzene; at 20℃;Inert atmosphere;	A solution of nonanoyl chloride (1.5 eq., 0.68 mmol, 120 mg) in benzene (5 mL) was added to a solution of 38b (0.45 mmol, 360 mg) and triethylamine (5 eq, 2.25 mmol, 228 mg, 314 uL) and DMAP (10 mg) in benzene (10 mL) at RT in 2 min under Ar. After addition, the mixture was stirred at RT overnight. MeOH (1 mL) was added and the mixture continued to stir 2h. The crude was filtered through a pad of silica gel. The filtrate was concentrated. The residue (457 mg) was purified by flash column chromatography on silica gel (230-400 mesh silica gel, 40 g, MeOH in chloroform, 0 to 4.6%). This gave the desired product (38) as a colorless oil (410 mg, 0.44 mmol, 98%). 1 HNMR (400 MHz, CDCl3) delta: 4.61-4.35 (br., estimated 0.4H, due to slow isomerization about amide bond), 3.974, 3.964 (two sets of doublets, 5.7 Hz, 4H), 3.64 (quintet-like, 7.0 Hz, 0.6H), 3.14-3.08 (m, 2H), 2.34-2.25 (m, 8H), 2.23 (broad s, 6H), 1.77-1.58 (m, 10H), 1.53-1.39 (m, 4H), 1.37-1.15 (66H), 0.92-0.86 (m, 15H).
98%	With dmap; triethylamine; In benzene; at 20℃;Inert atmosphere;	A solution of nonanoyl chloride (1.5 eq., 0.68 mmol, 120 mg) in benzene (5 mL) was added to a solution of II-38b (0.45 mmol, 360 mg) and triethylamine (5 eq, 2.25 mmol, 228 mg, 314 muL) and DMAP (10 mg) in benzene (10 mL) at room temperature in 2 min under argon atmosphere. After addition, the mixture was stirred at room temperature overnight. MeOH (1 mL) was added and the mixture continued to stir 2h. The crude was filtered through a pad of silica gel. The filtrate was concentrated. The residue (457 mg) was purified by flash column chromatography on silica gel (230-400 mesh silica gel, 40 g, MeOH in chloroform, 0 to 4.6%). This gave the desired product, compound II-38 as a colorless oil (410 mg, 0.44 mmol, 98%).1H NMR (400 MHz, CDCl3) delta: 4.61-4.35 (br., estimated 0.4H, due to slow isomerization about amide bond), 3.974, 3.964 (two sets of doublets, 5.7 Hz, 4H), 3.64 (quintet-like, 7.0 Hz, 0.6H), 3.14-3.08 (m, 2H), 2.34-2.25 (m, 8H), 2.23 (broad s, 6H), 1.77-1.58 (m, 10H), 1.53-1.39 (m, 4H), 1.37-1.15 (66H), 0.92- 0.86 (m, 15H).

Reference： [1]Patent: US2016/376224,2016,A1 .Location in patent: Paragraph 0220
[2]Patent: WO2018/81480,2018,A1 .Location in patent: Page/Page column 134

75
[ 764-85-2 ]
[ 89-83-8 ]
thymyl nonanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79.8%	With triethylamine; In dichloromethane; at 0℃; for 3h;Reflux;	General procedure: Series of thymyl esters were made following theprocedure described by Paolini et al.39 A solution of acidchloride (4.5 mmol) in CH2Cl2 (15 mL) was added dropby drop to a cooled mixture (0 C) of thymol (3.3 mmol)and Et3N (4.5 mmol) in CH2Cl2 (20 mL). The mixture wasstirred at room temperature and then refluxed for 3 h. The organic layer was washed with water (3 × 200 mL), driedover anhydrous Na2SO4 and concentrated under vacuum.The esters were purified by column chromatography, stationaryphase Silica Gel 60 (70-230 mesh), mobile phase(hexane/diethyl ether, gradient 9:1 to 8:2).

Reference： [1]Acta Chimica Slovenica,2017,vol. 64,p. 603 - 612

76
[ 764-85-2 ]
[ 76-37-9 ]
[ 201230-82-2 ]
C₁₆H₂₂F₈O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%		General procedure: At - 20 oC ( - 40 oC, or 0 oC), under atmospheric CO pressure, the acyl halide (0.5 - 2.0 mmol) was added to a stirred solution of CBr4·2AlBr3 (1-4 mmol) freshly prepared from CBr4 and AlBr3 in the molar ratio [2]:[1] in anhydrous CH2Br2 (1.5-3.6 mL) at room temperature. After stirring for 1-2 h at the same temperature under a CO atmosphere, the appropriate nucleophile was added to the in situ prepared carbonylation intermediate strictly under CO. The mixture was stirred for 10-20 min at -20 oC or at - 40 oC and then left to warm to 0 . Next, H2O (10 mL) and CHCl3 (30 mL) were carefully added to the mixture. The organic layer was separated and the remaining aqueous layer extracted with CHCl3 (10 mL). The combined organic extracts were washed with H2O until neutral, and dried over Na2SO4. The structures of the products were established by 1H, 13C, and 19F NMR spectroscopy, and from GC-MS spectra; conversions and isomeric ratios were determined by GC. To perform NMR measurements, all the solvents and highly volatile compounds were removed under reduced pressure. In some cases, in order to remove by-products, the product was washed with a suitable solvent and dried under vacuum or was purified by column chromatography (silica gel) using hexane-acetone as an eluent. The yields of the products were determined by 1H NMR spectroscopy with mesitylene as an internal standard In the presented below experiments, carbonylation of acyl halides was carried out at - 20 0 C for 1.45 h. Other carbonylation conditions are indicated in each case

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 4014 - 4019

77
[ 764-85-2 ]
[ 75-89-8 ]
[ 201230-82-2 ]
C₁₄H₂₀F₆O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%		General procedure: At - 20 oC ( - 40 oC, or 0 oC), under atmospheric CO pressure, the acyl halide (0.5 - 2.0 mmol) was added to a stirred solution of CBr4·2AlBr3 (1-4 mmol) freshly prepared from CBr4 and AlBr3 in the molar ratio [2]:[1] in anhydrous CH2Br2 (1.5-3.6 mL) at room temperature. After stirring for 1-2 h at the same temperature under a CO atmosphere, the appropriate nucleophile was added to the in situ prepared carbonylation intermediate strictly under CO. The mixture was stirred for 10-20 min at -20 oC or at - 40 oC and then left to warm to 0 . Next, H2O (10 mL) and CHCl3 (30 mL) were carefully added to the mixture. The organic layer was separated and the remaining aqueous layer extracted with CHCl3 (10 mL). The combined organic extracts were washed with H2O until neutral, and dried over Na2SO4. The structures of the products were established by 1H, 13C, and 19F NMR spectroscopy, and from GC-MS spectra; conversions and isomeric ratios were determined by GC. To perform NMR measurements, all the solvents and highly volatile compounds were removed under reduced pressure. In some cases, in order to remove by-products, the product was washed with a suitable solvent and dried under vacuum or was purified by column chromatography (silica gel) using hexane-acetone as an eluent. The yields of the products were determined by 1H NMR spectroscopy with mesitylene as an internal standard In the presented below experiments, carbonylation of acyl halides was carried out at - 20 0 C for 1.45 h. Other carbonylation conditions are indicated in each case

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 4014 - 4019

78
[ 764-85-2 ]
[ 4981-66-2 ]
9,10-bis(n-nonanoyloxy)anthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3.53 g		thermometer, In a 200 ml three-necked flask equipped with a stirrer, under a nitrogen atmosphere, 2.10 g (10.0 mmol) of 9,10-dihydroxyanthracene was reslurried in 20 g of deaerated water and a solution of 0.92 g (23.0 mmol) of sodium hydroxide dissolved in 3 g of degassed water was added, An aqueous solution of a disodium salt of 10-dihydroxyanthracene as an enriched color was prepared. To this aqueous solution was added 20 mg of tetrabutylammonium bromide and while cooling with ice water, a solution of 3.88 g (22.0 mmol) of n-nonanoyl chloride in 22 g of toluene was added. After the addition, the mixture was stirred for 2 hours, and the aqueous layer was separated. Then, the toluene layer was washed twice with 10 ml of water, then 40 ml of methanol was added and concentrated. Precipitated crystals were suction filtered and dried to obtain 3.53 g (7.2 mmol) of 9,10-bis (n-nonanoyloxy) anthracene white crystals. The yield based on the raw material 9,10-dihydroxyanthracene was 72 molpercent.

Reference： [1]Patent: JP6299235,2018,B2 .Location in patent: Paragraph 0077

79
[ 764-85-2 ]
[ 60-32-2 ]
6-nonanoylaminohexanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With sodium carbonate; In tetrahydrofuran; water; at 0 - 20℃; for 7h;	General procedure: To a solution of 9-aminononanoic acid 4a (0.457 g, 1.90 mmol) and Na2CO3 (0.302 g, 2.85 mmol) in THF (15 mL) and H2O (15 mL) at 0 C was added n-hexanoyl chloride 3a (0.261 mL, 1.90 mmol). The reaction mixture was warmed to r.t. and stirred for 7 h. After suspension was quenched by an addition of saturated KHSO4 aq. and extracted with CHCl3. The organic layer was washed with brine and dried Na2SO4, filtered and concentrated in vacuo. The residue was purified by column chromatography of SiO2 with CHCl3-MeOH (5:1 = in vol. ratio) to give 5a (0.296 g, 57%) as a white solid.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 1638 - 1641

80
[ 764-85-2 ]
[ 624-08-8 ]

Reference： [1]Patent: US2018/169268,2018,A1

81
[ 764-85-2 ]
4'-(tert-butylthio)-(1,1'-biphenyl)-4-carbonitrile [ No CAS ]
S-(4'-cyano-(1,1'-biphenyl)-4-yl) nonanethioate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With bismuth(lll) trifluoromethanesulfonate; In acetonitrile; at 20℃; for 1h;	To a suspension of 11 (40 mg, 0.150 mmol) and nonanoylchloride 8e (0.30 mL) in CH3CN (1.0 mL) was added Bi(OTf)3(31 mg, 0.047 mmol) and the resulting solution was stirred at RTfor 1 h. The reaction mixture was added to cold saturatedaqueous NaHCO3 (20 mL) and extracted with small portionsof CH2Cl2 (20 mL in total). The combined organics were passedthrough a pad of cotton wool and the solvent removed underreduced pressure. The residue was purified by flash columnchromatography (gradient elution 66% CH2Cl2/heptane toCH2Cl2) to give 5e (46 mg, 87 %) as a white solid. Mp Cr45.38C SmA 53.58C N 60.28C Iso. Rf 0.35 (66% CH2Cl2/heptane). dH (500 MHz, CDCl3) 7.74 (d, J 8.6, 2H), 7.69 (d, J8.6, 2H), 7.62 (d, J 8.5, 2H), 7.52 (d, J 8.5, 2H), 2.69 (t, J 7.5, 2H),1.73 (quintet, J 7.5, 2H), 1.41-1.24 (m, 10H), 0.89 (t, J 7.1, 3H). dC (125 MHz, CDCl3) 197.4, 144.8, 140.2, 135.2, 132.8, 128.9,128.0, 128.0, 118.9, 111.6, 44.1, 31.9, 29.4, 29.2, 29.1, 25.8,22.8, 14.2. m/z (ESMS ve) 352 ([M H]). Anal. Calc. forC22H25NOS (351.51): C 75.17, H 7.17, N 3.98; found C 75.14,H 7.02, N 3.87 %.

Reference： [1]Australian Journal of Chemistry,2018,vol. 71,p. 422 - 434

82
[ 764-85-2 ]
1,4-bis[4-(tert-butylthio)phenyl]buta-1,3-diyne [ No CAS ]
S,S'-(buta-1,3-diyne-1,4-diylbis(4,1-phenylene))dinonanethioate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With bismuth(lll) trifluoromethanesulfonate; In toluene; acetonitrile; at 20℃; for 1h;	To a suspension of 12 (29 mg, 0.0766 mmol) and nonoylchloride 8e (0.30 mL) inCH3CN(1.0 mL) and toluene (0.50 mL)was added Bi(OTf)3 (31 mg, 0.047 mmol) and the resultingsolution was stirred at RT for 1 h. The reaction mixture wasadded to cold saturated aqueous NaHCO3 (20 mL) and extractedwith small portions of CH2Cl2 (20 mL in total). The combinedorganics were passed through a pad of cotton wool and thesolvent removed under reduced pressure. The residue waspurified by flash column chromatography (40% CH2Cl2/heptane) to give 6e (40 mg, 95 %) as a white solid. Mp Cr135.88C Cr2130.98C Iso. Rf 0.44 (50% CH2Cl2/heptane). dH(500 MHz, CDCl3) 7.54 (d, J 8.5, 4H), 7.39 (d, J 8.5, 4H), 2.66(t, J 7.5, 4H), 1.71 (quintet, J 7.5, 4H), 1.38-1.25 (m, 20H), 0.89(t, J 7.0, 6H). dC (125 MHz, CDCl3) 196.7, 134.4, 133.1, 129.8,122.7, 81.6, 75.4, 44.1, 31.9, 29.3, 29.2, 29.1, 25.7, 22.8, 14.2. m/z (ESMSve) 569 ([MNa]), 547 ([MH]). Anal. Calc.for C34H42O2S2 (546.83): C 74.68, H 7.74; found C 74.81, H7.65 %.

Reference： [1]Australian Journal of Chemistry,2018,vol. 71,p. 422 - 434

83
[ 764-85-2 ]
1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-7-(3-methylaminopiperidin-1-yl)-3-quinolinecarboxylic acid [ No CAS ]
C₂₉H₄₀FN₃O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
55.15%	With triethylamine; In N,N-dimethyl-formamide; at 0 - 20℃; for 24.5h;	Take 0.2g balofloxacin, round-bottom flask, 0 added 10mL DMF, the reaction constant stirring 10min, and 100muL of triethylamine was slowly added dropwise 190 l of nonanoyl chloride, stirred for 30min 0 , at room temperature and then stirred for 24h, to the reaction 2 volumes of water were added to the solution, extracted with dichloromethane, washed three times with water, and the organic phase was concentrated, washed with cold diethyl ether, and concentrated to give 0.15 g of a novel quinolone compound, yield 55.15% (see Figure 13 for the synthetic route)

Reference： [1]Patent: CN108864043,2018,A .Location in patent: Paragraph 0038; 0070; 0071

84
[ 764-85-2 ]
C₄₉H₉₈N₂O₄ [ No CAS ]
C₅₈H₁₁₄N₂O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With dmap; triethylamine; In benzene; at 20℃; for 1.03333h;	A solution of nonanoyl chloride (1.4 eq., 0.42 mmol, 74 mg) in benzene (5 mL) was added to a solution of compound 7-1 (0.3 mmol, 234 mg) and triethylamine (5 eq, 1.5 mmol, 152 mg) and DMAP (5 mg) in benzene (5 mL) at RT in 2 min. After addition, the reaction mixture was stirred at RT for lh. MeOH (0.5 mL) was added to remove any excess acyl chloride. After 16 hours, the reaction mixture was filtered through a pad of silica gel. The pad was washed with a mixture of hexane/EtOAc/Et3N (70:30: 1). Concentration of the filtrate and the washing gave a colorless oil. The crude product was purified by flash dry column chromatography on silica gel MeOH in chloroform, 0 to 5%). The desired product was obtained as a colorless oil (224 mg, colorless oil, 0.24 mmol, 81%).

Reference： [1]Patent: WO2019/36000,2019,A1 .Location in patent: Page/Page column 69

85
[ 764-85-2 ]
[ 1596-64-1 ]
N-pelargonylhistidinol [ No CAS ]

Reference： [1]Journal of Agricultural and Food Chemistry,2019,vol. 67,p. 3670 - 3678

86
[ 764-85-2 ]
[ 498-63-5 ]
C₂₈H₅₃N₂O₆P [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		1) Proline alcohol (47.6 mmol, 4.8 g) was sequentially added to the reactor. 40mL of acetone, 20mL water, Sodium hydroxide (95.2 mmol, 10 g), Cool down to 0 C, Octanoyl chloride (shown by Formula II-d) (47.6 mmol, 7.74 g) was added dropwise. After 5 hours of reaction, the mixture was extracted with dichloromethane, Washed, Rotary evaporation gave a white solid. 2) The above white solid (17.4 mmol, 4.9 g), Soluble in 50mL of dichloromethane, Add triethylamine (52.2 mmol, 5.28 g), Phosphorus oxychloride (8.7 mmol, 1.33 g) was added dropwise thereto. After 12 hours of reaction, Add 5mL of water, Reflux for 4 hours, Washed in 6 mol/L hydrochloric acid solution and water, dry, Rotating to give a white solid, Recrystallization of ethanol gave bis(N-octanoyldeaminone)-phosphoric acid (shown by Formula I-d).

Reference： [1]Patent: CN109694388,2019,A .Location in patent: Paragraph 0049-0053

87
[ 764-85-2 ]
[ 46843-68-9 ]
N-2-nonanoyl-N'-6-benzyl-L-lysine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With potassium carbonate; In tetrahydrofuran; water; at 20℃; for 1h;	2.9 g of potassium carbonate and 10 ml of water were sequentially added to the reaction flask.Tetrahydrofuran 10ml, N-6-benzyl-L-lysine 1.0g,0.89 g of nonanoyl chloride was added dropwise at room temperature, the dropwise addition was completed, the reaction for 1 hour, the reaction completion,The tetrahydrofuran was removed under reduced pressure at 30 to 40 C, and then adjusted to pH 2.0 with hydrochloric acid, and suction filtered.The filter cake was dried to give N-2- nonanoyl -N-6-benzyl--L- lysine 1.2g, 97% content, 73% yield.

Reference： [1]Patent: CN109704986,2019,A .Location in patent: Paragraph 0049; 0050

88
[ 764-85-2 ]
[ 5981-09-9 ]
N-{4-[bis(4-nonanamidophenyl)amino]phenyl}nonanamide [ No CAS ]

Reference： [1]Chemistry - A European Journal,2019,vol. 25,p. 13008 - 13016

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[ CAS No. 764-85-2 ] {[proInfo.proName]}

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[ 764-85-2 ] Synthesis Path-Upstream 1~5

[ 764-85-2 ] Synthesis Path-Downstream 1~88

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