Name: 38460-95-6|10-Undecenoylchloride|99%
Brand: Ambeed
SKU: A122363
Price: 10.0 USD
Availability: InStock
Rating: 95 (27 reviews)

1
[ 123-75-1 ]
[ 38460-95-6 ]
[ 95018-99-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With triethylamine In dichloromethane at 20℃; for 14h; Inert atmosphere;
100%	With triethylamine In dichloromethane at 0 - 23℃; for 14h;
100%	With triethylamine In dichloromethane at 0 - 23℃; for 14h;	1 -(1-Pyrrolidinyl)-10-undecen-1 -one (1a) To a solution of pyrrolidine (0.452 ml_, 0.391 g, 5.5 mmol, 1.1 equiv.) and triethylamine (1 39 mL, 1.012 g, 10 mmol, 2.00 equiv.) in DCM (20 mL) at 0 °C, 10-undecenoyl chloride (1.08 mL, 1.014 g, 5 mmol, 1 equiv.) was added dropwise and the resulting reaction mixture was allowed to warm to room temperature while stirring overnight (14 h). After this time, a saturated aqueous solution of sodium bicarbonate was added and the biphasic system was separated. The aqueous phase was extracted with DCM (1 *) and the organic phases were combined and dried over anhydrous sodium sulfate. The dried solution was filtered and concentrated under reduced pressure. The resulting crude material was purified by flash column chromatography on silica gel (heptane/ethyl acetate) to afford the desired compound; Quant.; 1H NMR (400 MHz, CDCI3) d 5.80 (ddt, J = 16.9, 10.2, 6.7 Hz, 1 H), 4.97 (ddd, = 17.1 , 3.7, 1.6 Hz, 1 H), 4.91 (ddt, J = 10.2, 2.3, 1.2 Hz, 1 H), 3.45 (t, J = 6.9 Hz, 2H), 3.39 (t, J = 6.8 Hz, 2H), 2.25-2.03 (m, 2H), 2.01-1.99 (m, 2H), 1.97-1.95 (m, 2H), 1.87-1.80 (m, 2H), 1.65-1.59 (m, 2H), 1.39-1.22 (m, 10H).

99%	With triethylamine In dichloromethane at 0 - 20℃; for 14h; Inert atmosphere;
75%	With sodium hydrogencarbonate In tetrahydrofuran; water at 0 - 20℃; for 2h; Inert atmosphere;
	With benzene

Reference： [1]De La Torre, Aurélien; Kaiser, Daniel; Maulide, Nuno [Journal of the American Chemical Society, 2017, vol. 139, # 19, p. 6578 - 6581] Kaiser, Daniel; Teskey, Christopher J.; Adler, Pauline; Maulide, Nuno [Journal of the American Chemical Society, 2017, vol. 139, # 45, p. 16040 - 16043]
[2]Kaiser, Daniel; Tona, Veronica; Gonçalves, Carlos R.; Shaaban, Saad; Oppedisano, Alberto; Maulide, Nuno [Angewandte Chemie - International Edition, 2019, vol. 58, # 41, p. 14639 - 14643][Angew. Chem., 2019, vol. 131, # 41, p. 14781 - 14785,5]
[3]Current Patent Assignee: UNIVERSITY OF VIENNA - WO2019/219942, 2019, A1 Location in patent: Page/Page column 60-61
[4]Gonçalves, Carlos R.; Lemmerer, Miran; Teskey, Christopher J.; Adler, Pauline; Kaiser, Daniel; Maryasin, Boris; González, Leticia; Maulide, Nuno [Journal of the American Chemical Society, 2019, vol. 141, # 46, p. 18437 - 18443]
[5]Zhang, Fengzhi; Das, Shoubhik; Walkinshaw, Andrew J.; Casitas, Alicia; Taylor, Michael; Suero, Marcos G.; Gaunt, Matthew J. [Journal of the American Chemical Society, 2014, vol. 136, # 25, p. 8851 - 8854]
[6]Coan; Papa [Journal of the American Chemical Society, 1955, vol. 77, p. 2402] Szeki [1936, vol. 54, p. 807,816][Chemisches Zentralblatt, 1937, vol. 108, # I, p. 1690]

2
[ 110-89-4 ]
[ 38460-95-6 ]
[ 22342-20-7 ]

Yield	Reaction Conditions	Operation in experiment
99%	With 1-methyl-1H-imidazole; N,N,N,N,-tetramethylethylenediamine; potassium carbonate In acetonitrile at 0 - 5℃; for 1h;
84%	In tetrahydrofuran for 3h; Reflux;	1 10-undecenoic acid (3.7 g, 0.02 mol), the thionyl chloride and (8 mL) was added, and refluxed in water bath for 2 hours.Then, the excess of thionyl chloride was distilled off under reduced pressure to give the 10-undecenoic acid chloride. Then, the 10-undecenoic acid chloride was dissolved in tetrahydrofuran (THF) (20mL), was prepared acid chloride solution. On the other hand, piperidine (3.4 g, 0.04 mol), was dissolved in THF (30mL). Then, piperidine solution was added dropwise to a carboxylic acid chloride solution to obtain a reaction liquid. After the reaction solution was refluxed for 3 h on a water bath under reduced pressure, THF in the reaction solution was distilled off. Then, water and ethyl acetate to the reaction solution was added to distribution, it was to separate the ethyl acetate layer was separated.After the ethyl acetate layer was once washed with water, by distilling off the ethyl acetate, to give the crude product. The crude product was purified by silica gel column chromatography (developing solvent: chloroform) to give 1- (piperidin-1-yl) Undekku -10-en-1-one(C 16H 29 NO) (in the chemical formula 3 considerable), as a pale brown oil. Yield: 4.2 g, Yield: 84%
	With benzene

With triethylamine In dichloromethane at 20℃; for 1h;

Reference： [1]Nakatsuji, Hidefumi; Morimoto, Mami; Misaki, Tomonori; Tanabe, Yoo [Tetrahedron, 2007, vol. 63, # 48, p. 12071 - 12080]
[2]Current Patent Assignee: OSAKA GAS CO LTD - JP5689293, 2015, B2 Location in patent: Paragraph 0132-0139
[3]Coan; Papa [Journal of the American Chemical Society, 1955, vol. 77, p. 2402] Szeki [1936, vol. 54, p. 807,816][Chem.Abstr., 1937, p. 5355]
[4]Fernandez-Salas, Jose A.; Manzini, Simone; Nolan, Steven P. [Chemical Communications, 2013, vol. 49, # 84, p. 9758 - 9760]

3
[ 578-68-7 ]
[ 38460-95-6 ]
undec-10-enoic acid-[4]quinolylamide [ No CAS ]

Reference： [1],1936,vol. 54,p. 807,816
Chemisches Zentralblatt,1937,vol. 108,p. 1690

5
[ 38460-95-6 ]
[ 1598-93-2 ]

Yield	Reaction Conditions	Operation in experiment
89%	With potassium hydrogenfluoride; tetrabutyl-ammonium chloride; water In dichloromethane at 20℃; for 1h;	Preparation of Acyl Fluorides 2; General Procedure General procedure: A 250 mL round-bottomed flask was charged with potassium bifluoride(15.62 g, 200 mmol) and water (40.17 g), and stirred at ambienttemperature for 1 h. Then tetrabutylammonium chloride (0.279 g, 1.0mmol, 1 mol%), DCM (used in two-fold volume of acyl chloride) andacyl chloride (1a-y; 100 mmol) were added, and the mixture wasstirred (1400 rpm) with a magnetic bar (fish; 15 × 33 mm) at r.t. forthe time given in the characterization data. The mixture was thentransferred to a separatory funnel, separated, and the aqueous phasewas extracted with DCM (50 mL). The combined organic phases werewashed with brine (50 mL), and dried with MgSO4. The mixture wasfiltered and evaporated, and the residue was distilled under reducedpressure to obtain product 2a-y.
	With potassium fluorosulphinate

Reference： [1]Tryniszewski, Michał; Barbasiewicz, Michał [Synthesis, 2022, vol. 54, # 5, p. 1446 - 1460]
[2]Seel; Langer [Chemische Berichte, 1958, vol. 91, p. 2553,2557]

6
[ 112-38-9 ]
[ 38460-95-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	With thionyl chloride
95%	With thionyl chloride; N,N-dimethyl-formamide In benzene Reflux;
90%	With oxalyl dichloride In benzene for 3h; Ambient temperature;

88%	With thionyl chloride for 2h; Heating;
84%	With thionyl chloride In dichloromethane for 4h; Reflux;
83%	With thionyl chloride; N,N-dimethyl-formamide at 80℃; for 10h; Inert atmosphere; Sealed tube;
83%	With thionyl chloride; N,N-dimethyl-formamide at 80℃; for 10h; Inert atmosphere; Schlenk technique;
61%	With thionyl chloride at 20 - 60℃; for 5h;
55%	With thionyl chloride; hydroquinone at 65℃; for 6h;	3.2.2.1 (2.1) Preparation of intermediate undecenoyloxybenzoyl chloride: Dissolve 18.43g (0.10mol) of undecylenic acid and 16mL (0.20mol) of thionyl chloride in a 100mL three-necked flask, add a small amount of hydroquinone as a polymerization inhibitor, heat to reflux at 65°C for 6h, after the reaction is complete At 65°C, vacuum distillation was performed to remove excess thionyl chloride. The temperature was continued to increase, and the fractions at 139.0157.0°C/1.30KPa were collected to obtain the product undecenoyl chloride with a yield of 55%. In a 250mL three-necked flask, dissolve 16.57g (0.12mol) of p-hydroxybenzoic acid in 150mL of THF and 9.5mL of pyridine, stir until clear, and slowly add 0.10mol of undecenoyl chloride in THF solution at room temperature. Reaction for 10h, heating and refluxing for 10h. After the reaction is completed, pour the reaction solution into 1000 mL of water, add 37% concentrated hydrochloric acid to acidify the system, make the system appear strongly acidic, let stand overnight, filter with suction, wash the filter cake to neutral, then wash with hot water, and wait for the filter cake After drying, it was recrystallized with ethanol to obtain powder undecenoyloxy benzoic acid with a yield of 80%. In a 100mL round bottom flask, dissolve 9.13g (0.03mol) of undecenoyloxybenzoic acid in 20mL of thionyl chloride, and heat to reflux for 6h at 65°C in an oil bath. After the reaction is completed, vacuum distillation is carried out. A light yellow transparent liquid undecenoyloxy benzoyl chloride was obtained with a yield of 68%.
	With thionyl chloride
	With phosphorus pentachloride
	With thionyl chloride In benzene
	With oxalyl dichloride
	With thionyl chloride; N,N-dimethyl-formamide at 40℃; for 2h;
	With phosphorus pentachloride In benzene Heating;
	With oxalyl dichloride for 3h;
	With thionyl chloride for 12h; Heating;
	With oxalyl dichloride In toluene
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane
	With thionyl chloride for 4h; Ambient temperature;
	With oxalyl dichloride In dichloromethane at 20℃; for 2h;
	With thionyl chloride In dichloromethane for 10h; Heating;
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane for 1h;
	With oxalyl dichloride In dichloromethane at 20℃; for 1h;
	With oxalyl dichloride In dichloromethane at 20℃; for 2h;
	With thionyl chloride at 80℃; for 2h;
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 25℃; Inert atmosphere;
	With phosphorus trichloride at 70℃; for 2h;
	With thionyl chloride
	With phosphorus trichloride at 70℃; for 3h;	4.1.8. General procedure for the synthesis of aurone fatty acid esters General procedure: A solution of fatty acid (3.75 mmol) and PCl3 (1.5 mmol) was stirred at 70 °C for 3 h, and a yellow solution containing fatty acid chloride could be gotten.A solution of aurone (1.86 mmol) and anhydrous pyridine (1 mL) in CH2Cl2 (10 mL) was stirred at boiling temperature, and the above reaction mixture was added slowly. Then the reaction continued for 1-2 h at boiling temperature. Washing with dilute hydrochloric acid (10% v/v aqueous solution), saturated NaHCO3 solution, drying (Na2SO4) and removal of solvent under reduced pressure gives the crude product. The product was further purified either by flash column chromatography or recrystallization.
	With oxalyl dichloride In tetrahydrofuran at 0℃; for 2h; Inert atmosphere;
	With thionyl chloride In toluene for 1.5h; Reflux;	23 A mixture of toluene (12 mL) and SOCl2 (7.75 g, 65 mmol) and undec-10-enoic acid (1.00 g, 5.43 mmol) were refluxed for 1.5 h. The solvent and remaining SOCl2 were distilled off and the product (X) was further used in the thioester synthesis.
	With oxalyl dichloride; N,N-dimethyl-formamide In tetrahydrofuran at 0 - 23℃; for 1.08333h; Inert atmosphere;
	With thionyl chloride at 55℃;
	With thionyl chloride for 1.5h; Reflux;
	With thionyl chloride for 1.5h; Reflux;
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0℃; for 3h; Inert atmosphere;	General procedure for the synthesis of fatty acid chlorides (10a-h): General Procedure: General procedure: To a stirred solution of fatty acid in DCM, catalytic amount of DMF was added. The contents were stirred at 0 °C. Oxalyl chloride was added under nitrogen atmosphere. The reaction mixture was further stirred at 0 °C for 3 h. Then reaction mixture was concentrated under reduced pressure to remove dichloromethane and excess of oxalyl chloride traces. Later crude acid chloride dissolved in DCM was used for the next step directly under nitrogen atmosphere.
	With thionyl chloride for 3h; Heating;	9 Reference Production Example 9 (Trans-10-undecenoic acid methyl ester, compound 22) Trans-10-undecenoic acid was dissolved in thionyl chloride (10 ml) and treated in water bath for 3 hours to distill off excess thionyl chloride. Methanol (30 ml) was added to chloride of trans-10-undecenic acid and refluxed in water bath for 2 hours. After cooling, the reaction mixture was added to 1N HCl (80 ml) to be acidic and distributed with EtOAc. The distributed liquid was purified with column chromatography (developing solvent: C6H14-EtOAc (3:1)) after concentration, and trans-10-undecenoic acid methyl ester shown in the following was isolated. Colorless oily substance, C12H22O2 MW 198, EIMS m/z (%): 198 (M+, 0), 166 (M+ - CH3OH, 22), 149 (13), 124 (36), 87 (53), 74 (100)
	With thionyl chloride; N,N-dimethyl-formamide; sodium hydroxide In dichloromethane; water for 1.5h; Reflux;
	With thionyl chloride for 1.5h; Reflux;
	With thionyl chloride for 2h; Reflux;	1 10-undecenoic acid (3.7 g, 0.02 mol), the thionyl chloride and (8 mL) was added, and refluxed in water bath for 2 hours.Then, the excess of thionyl chloride was distilled off under reduced pressure to give the 10-undecenoic acid chloride
	With oxalyl dichloride In N,N-dimethyl-formamide at 20℃;
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0℃; for 3h; Inert atmosphere;	General Procedure for the Synthesis of Fatty Acid Chlorides (2a-2j) To a stirred solution of fatty acid in dichloromethane (DCM), catalytic amount of dimethyl formamide (DMF) was added and the contents were stirred at 0 °C. Oxalyl chloride was added under nitrogen atmosphere and the reaction mixture was further stirred at 0 °C for 3 h. Then reaction mixture was concentrated under reduced pressure to remove DCM and excess oxalyl chloride. Later crude acid chloride dissolved in DCM was used for the next step directly under nitrogen atmosphere.
	With thionyl chloride In N,N-dimethyl-formamide at 80℃; for 4h; Inert atmosphere;
	With thionyl chloride; N,N-dimethyl-formamide In toluene at 70℃; for 3h;
	With oxalyl dichloride at 20 - 35℃; for 3.5h; Inert atmosphere; Green chemistry;	21 Synthesis of undecylenoyl chloride by chlorination of undecylenic acid Using Catalyst of Example 9 To a stirred mixture of undecylenic acid (37 g,200.8 mmol) and the polymeric catalyst of Example 9 (0.75 g) at room temperature under nitrogen atmosphere, oxalyl chloride (28 g, 220.5 mmol) is added over 30 minutes. The reaction is continued at 30-35° C. and the progress of the reaction is monitored by estimating the unconverted fatty acid. The reaction was stopped after 3 hours when the free undecylenic acid was found to be less than 1.0% by weight.
	With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 20 - 22℃; for 1h;
	With thionyl chloride
	With thionyl chloride In dichloromethane at 10℃;	2.1 Step one amidation At room temperature, the reaction vessel was added 1250ml of dichloromethane and 50g 10-undecenoic acid, while stirring 129.1g of thionyl chloride was added dropwise, the reaction was completed at 10 ° C, the reaction was completed, concentration, to obtain A;
	With thionyl chloride In tetrahydrofuran for 2h; Reflux;
	With oxalyl dichloride In dichloromethane at 0 - 20℃; for 3.16667h; Inert atmosphere;
	With thionyl chloride
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃;
	With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0 - 20℃;	Acyl chlorides General procedure: The acid (5 mmol) was dissolved in anhydrous CH2Cl2 (10 mL) and DMF (a few drops) added.Oxalyl chloride (6 mmol, 1.2 equiv.) was added dropwise to the solution, that was cooled in an icewater bath. The resulting mixture was allowed to stir at room temperature for an additional 4 h andthe solvent was evaporated to afford the crude acyl chloride, which was used directly in the nextstep.

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[51]Vijayendar, Venepally; Kaki, Shiva Shanker; Vamshi Krishna; Misra, Sunil; Prasad; Jala, Ram Chandra Reddy [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2018, p. 1015 - 1022]
[52]Venkatesh, Yarra; Chaudhuri, Amrita; Mondal, Saugat; Shah, Sk. Sheriff; Singh, N. D. Pradeep [Organic Letters, 2020, vol. 22, # 1, p. 295 - 299]
[53]Lee, Minhan; Jung, Hoimin; Kim, Dongwook; Park, Jung-Woo; Chang, Sukbok [Journal of the American Chemical Society, 2020, vol. 142, # 28, p. 11999 - 12004]
[54]Flavell, Robert R.; Liu, Jianbo; Parker, Matthew F. L.; Toste, F. Dean; Wang, Sinan; Wilson, David M. [Chem, 2021, vol. 7, # 8, p. 2245 - 2255]

7
[ 38460-95-6 ]
[ 109-89-7 ]
[ 4899-94-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	With dmap; triethylamine In tetrahydrofuran at 22℃; for 18h; Inert atmosphere;
63.74%	In diethyl ether for 2h;	1 In a 500ml three-necked reaction flask equipped with a stirring device, dropping funnel and temperature juice, Add 40 mL of 10-undecenoyl chloride and 80 mL of ether. Slowly add 28 mL of diethylamine in the dropping funnel, Pay attention to the boiling situation and control the speed of adding diethylamine (about 1.5mL/min), Let the reaction process smooth. After dripping, continue to stir for 2h, and the reaction ends. Then add 70 mL of 5% by mass sodium hydroxide aqueous solution to the reactant, After thorough stirring, the liquid was separated, and the ether layer was extracted. The ether layer was washed once with a 5% aqueous sodium hydroxide solution. Then the ether layer is washed once with a volume fraction of 10% hydrochloric acid solution and water, It was dried with anhydrous sodium sulfate to obtain 44 mL of an ether layer. 44mL of ether layer is evaporated under reduced pressure to get the final product The crude extract of N,N-diethyl 10-undecenamide was 30.094 g, and the yield was 63.72%. Then acid-base the 30.094g crude extract sample (The mass fraction of 5% sodium hydroxide aqueous solution, Volume fraction 10% hydrochloric acid solution) washing, ether extraction, Evaporate under reduced pressure to achieve a purity of 95%, The purified N,N-diethyl 10-undecenamide was obtained. The sample is a pale yellow oily liquid with a slight hala smell.
	With benzene

In tetrahydrofuran at 0℃; for 2h; Inert atmosphere;

Reference： [1]Tappin, Nicholas D. C.; Michalska, Weronika; Rohrbach, Simon; Renaud, Philippe [Angewandte Chemie - International Edition, 2019, vol. 58, # 40, p. 14240 - 14244][Angew. Chem., 2019, vol. 131, # 40, p. 14378 - 14382,5]
[2]Current Patent Assignee: GUANGDONG ACADEMY OF SCIENCES - CN112194594, 2021, A Location in patent: Paragraph 0027-0030
[3]Coan; Papa [Journal of the American Chemical Society, 1955, vol. 77, p. 2402] Papa et al. [Journal of the American Chemical Society, 1950, vol. 72, p. 3885][Journal of the American Chemical Society, 1951, vol. 73, p. 5925]
[4]Mukherjee,P.; Pathak,B. [Journal of the Indian Chemical Society, 1973, vol. 50, p. 290 - 292]
[5]Wang, Xi; Ye, Yuxuan; Zhang, Songnan; Feng, Jiajie; Xu, Yan; Zhang, Yan; Wang, Jianbo [Journal of the American Chemical Society, 2011, vol. 133, # 41, p. 16410 - 16413]

8
[ 38460-95-6 ]
[ 4062-60-6 ]
[ 61797-57-7 ]

Reference： [1]Patent: DE2515146,1976,
Chem.Abstr.,1977,vol. 86
[2]Patent: DE2551483,1977,
Chem.Abstr.,1977,vol. 87

9
[ 38460-95-6 ]
[ 3114-70-3 ]
[ 61796-66-5 ]

Reference： [1]Patent: DE2515146,1976,
Chem.Abstr.,1977,vol. 86
[2]Patent: DE2551483,1977,
Chem.Abstr.,1977,vol. 87

10
[ 38460-95-6 ]
[ 1761-71-3 ]
[ 61796-68-7 ]

Reference： [1]Patent: DE2515146,1976,
Chem.Abstr.,1977,vol. 86
[2]Patent: DE2551483,1977,
Chem.Abstr.,1977,vol. 87

11
[ 38460-95-6 ]
[ 825-41-2 ]
[ 5540-56-7 ]

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

12
[ 38460-95-6 ]
[ 6864-37-5 ]
[ 61796-67-6 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine
	With triethylamine In tetrahydrofuran

Reference： [1]Current Patent Assignee: BAYER AG - DE2515146, 1976, A1 [Chem.Abstr., 1977, vol. 86, # 71947][Chem.Abstr., 1977, vol. 86, # 71947]
[2]Current Patent Assignee: BAYER AG - DE2551483, 1977, A1 [Chem.Abstr., 1977, vol. 87, # 67862][Chem.Abstr., 1977, vol. 87, # 67862]

13
[ 38460-95-6 ]
[ 28319-77-9 ]
[ No CAS ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1960,vol. 79,p. 661 - 674

14
[ 38460-95-6 ]
[ 10212-25-6 ]
(3aS)-3c-undec-10-enoyl-2t-undec-10-enoyloxymethyl-(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

15
[ 38460-95-6 ]
[ 54897-59-5 ]
[ 63632-97-3 ]

Reference： [1]Patent: DE2551483,1977,
Chem.Abstr.,1977,vol. 87

16
[ 38460-95-6 ]
[ 5332-51-4 ]

Yield	Reaction Conditions	Operation in experiment
93%	With ammonium hydroxide In tetrahydrofuran at 0℃;
86%	With ammonia
85%	With ammonia for 4h; Ambient temperature;

80%	With ammonia In tetrahydrofuran for 6h; Inert atmosphere;
	With ammonia In diethyl ether

Reference： [1]Reimann, Sophie; Danke, Varun; Beiner, Mario; Binder, Wolfgang H. [Journal of Polymer Science, Part A: Polymer Chemistry, 2017, vol. 55, # 22, p. 3736 - 3748]
[2]Bergmann, David J.; Campi, Eva M.; Roy Jackson; Patti, Antonio F.; Saylik, Dilek [Australian Journal of Chemistry, 2000, vol. 53, # 10, p. 835 - 844]
[3]Vig, O. P.; Trehan, I. R.; Kad, G. L.; Ghose, J. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1982, vol. 21, p. 784 - 786]
[4]Jee, Joo-Eun; Cheong, Jian Liang; Lim, Jaehong; Chen, Cheng; Hong, Soon Hyeok; Lee, Su Seong [Journal of Organic Chemistry, 2013, vol. 78, # 7, p. 3048 - 3056]
[5]Staroverov,S.M. et al. [Journal of general chemistry of the USSR, 1979, vol. 49, p. 2196 - 2198][Zhurnal Obshchei Khimii, 1979, vol. 49, p. 2487 - 2490]

17
[ 38460-95-6 ]
[ 99-96-7 ]
[ 133641-66-4 ]

Yield	Reaction Conditions	Operation in experiment
87.5%	With pyridine In dichloromethane at 0 - 40℃; for 6h;
80%	With pyridine In tetrahydrofuran at 20℃; for 10h; Reflux;	3.2.2.1 (2.1) Preparation of intermediate undecenoyloxybenzoyl chloride: Dissolve 18.43g (0.10mol) of undecylenic acid and 16mL (0.20mol) of thionyl chloride in a 100mL three-necked flask, add a small amount of hydroquinone as a polymerization inhibitor, heat to reflux at 65°C for 6h, after the reaction is complete At 65°C, vacuum distillation was performed to remove excess thionyl chloride. The temperature was continued to increase, and the fractions at 139.0157.0°C/1.30KPa were collected to obtain the product undecenoyl chloride with a yield of 55%. In a 250mL three-necked flask, dissolve 16.57g (0.12mol) of p-hydroxybenzoic acid in 150mL of THF and 9.5mL of pyridine, stir until clear, and slowly add 0.10mol of undecenoyl chloride in THF solution at room temperature. Reaction for 10h, heating and refluxing for 10h. After the reaction is completed, pour the reaction solution into 1000 mL of water, add 37% concentrated hydrochloric acid to acidify the system, make the system appear strongly acidic, let stand overnight, filter with suction, wash the filter cake to neutral, then wash with hot water, and wait for the filter cake After drying, it was recrystallized with ethanol to obtain powder undecenoyloxy benzoic acid with a yield of 80%. In a 100mL round bottom flask, dissolve 9.13g (0.03mol) of undecenoyloxybenzoic acid in 20mL of thionyl chloride, and heat to reflux for 6h at 65°C in an oil bath. After the reaction is completed, vacuum distillation is carried out. A light yellow transparent liquid undecenoyloxy benzoyl chloride was obtained with a yield of 68%.
	With pyridine

Stage #1: undec-10-enoyl chloride With pyridine In tetrahydrofuran Stage #2: 4-hydroxy-benzoic acid

Reference： [1]Lei, Lan; Han, Li; Ma, Hongwei; Zhang, Ruixue; Huang, Shuai; Shen, Heyu; Yang, Lincan; Li, Chao; Zhang, Songbo; Bai, Hongyuan; Ma, Qingchi; Li, Yang [Chemistry - A European Journal, 2020, vol. 26, # 49, p. 11199 - 11208]
[2]Current Patent Assignee: XUZHOU UNIVERSITY OF TECHNOLOGY - CN113201008, 2021, A Location in patent: Paragraph 0116; 0121-0123
[3]Fiedler [Pharmazie, 1965, vol. 20, # 7, p. 401 - 404]
[4]Location in patent: scheme or table Xu, Xiao-Xu; Hong, Zhe; Liu, Fei [Molecular Crystals and Liquid Crystals, 2010, vol. 533, p. 52 - 62]

18
[ 6066-82-6 ]
[ 38460-95-6 ]
[ 110661-49-9 ]

Yield	Reaction Conditions	Operation in experiment
89%	With triethylamine In dichloromethane at 0 - 20℃;
	With triethylamine In dichloromethane a) 1h, 0 deg C, b) 24h, room temperature;
	With triethylamine In tetrahydrofuran at 0 - 20℃;

Reference： [1]Boman, Faith C.; Musorrafiti, Michael J.; Gibbs, Julianne M.; Stepp, Brian R.; Salazar, Anne M.; Nguyen, SonBinh T.; Geiger, Franz M. [Journal of the American Chemical Society, 2005, vol. 127, # 44, p. 15368 - 15369]
[2]Losset, D.; Dupas, G.; Duflos, J.; Bourguignon, J.; Queguiner, G. [Bulletin de la Societe Chimique de France, 1991, # 5, p. 721 - 729]
[3]Orner, Brendan P.; Derda, Ratmir; Lewis, Rachel L.; Thomson, James A.; Kiessling, Laura L. [Journal of the American Chemical Society, 2004, vol. 126, # 35, p. 10808 - 10809]

19
[ 38460-95-6 ]
[ 10191-18-1 ]
[ 79898-74-1 ]

Yield	Reaction Conditions	Operation in experiment
85%	With pyridine In chloroform Heating;

Reference： [1]Tundo; Kippenberger; Klahn; Prieto; Jao; Fendler [Journal of the American Chemical Society, 1982, vol. 104, # 2, p. 456 - 461]

20
[ 38460-95-6 ]
[ 14426-21-2 ]
[ 79898-77-4 ]

Reference： [1]Journal of the American Chemical Society,1982,vol. 104,p. 456 - 461

21
[ 38460-95-6 ]
[ 112-45-8 ]

Yield	Reaction Conditions	Operation in experiment
92%	With tri-n-butyl-tin hydride; triphenylphosphine In tetrahydrofuran at -30℃; for 2h;
91%	With ammonium hydroxide; formic acid In diethyl ether; chloroform for 0.583333h; Ambient temperature;
86%	With tri-n-butyl-tin hydride In benzene for 1h; Ambient temperature;

40%	With iron(II) oxide; tris(2,4,6-trimethoxyphenyl)phosphine; phenylsilane In toluene at 60℃; for 2h; Inert atmosphere; Schlenk technique;	Catalytic reaction General procedure: A typical procedure for the iron oxide catalyzed reduction of 3-phenylpropionyl chloride (1a) with H3SiPh (Table1 , entry 1): iron oxide (3.6mg, 0.050mmol) and TMPP (6.7mg, 0.013mmol) were added to a 10mL Schlenk flask with a magnetic stir bar. The flask was evacuated and backfilled with argon three times. Then, H3SiPh (34μL, 0.28mmol) was added to the flask and the reaction mixture was stirred at 60°C for 20h under an argon atmosphere. Then, toluene (0.50mL) was added to the flask and the resultant solution was stirred at room temperature for 5min before 1a (37μL, 0.25mmol) was loaded. Further, the reaction mixture was stirred at 60°C for 20h under an argon atmosphere. After cooling to room temperature, the reaction mixture was diluted with diethyl ether (5.0mL) and tetradecane (50μL, 0.19mmol) as an internal standard was added. The yield of 3-phenylpropanal (2a; 57%) was analyzed by gas chromatography. 2a was isolated by silica gel column chromatography (hexane: EtOAc=13: 1). Pale yellow oil (16.8mg) was obtained in 50% yield.
60 % Chromat.	With 4(P(C₆H₅)3)2Cu⁽¹⁺⁾2(BH₃)*2(CN)^(1-)={(P(C₆H₅)3)2CuBH₃(CN)}2 In acetone for 3h; Ambient temperature;
	Multi-step reaction with 3 steps 1: K₂CO₃ 2: acetone 3: 69 percent / diisobutylaluminum hydride / tetrahydrofuran / 0.5 h / -10 - 20 °C
	Multi-step reaction with 2 steps 1: Et₃N / CH₂Cl₂ 2: (i) LiAlH₄, tBuOH, (ii) aq. H₂SO₄, Na₂SO₄

Reference： [1]Inoue, Katsuyuki; Yasuda, Makoto; Shibata, Ikuya; Baba, Akio [Tetrahedron Letters, 2000, vol. 41, # 1, p. 113 - 116]
[2]Shamsuddin; Zobairi, Md. Omair; Musharraf, Mohd. Asif [Tetrahedron Letters, 1998, vol. 39, # 44, p. 8153 - 8154]
[3]Four, P.; Guibe, F. [Journal of Organic Chemistry, 1981, vol. 46, # 22, p. 4439 - 4445]
[4]Cong, Cong; Fujihara, Tetsuaki; Terao, Jun; Tsuji, Yasushi [Catalysis Communications, 2014, vol. 50, p. 25 - 28]
[5]Hutchins, Robert O.; Markowitz, Morris [Tetrahedron Letters, 1980, vol. 21, p. 813 - 816]
[6]De Las Heras, Maria A.; Vaquero, Juan J.; Garcia-Navio, Josel; Alvarez-Builla, Julio [Tetrahedron Letters, 1995, vol. 36, # 3, p. 455 - 458]
[7]Izawa,T.; Mukaiyama,T. [Bulletin of the Chemical Society of Japan, 1979, vol. 52, p. 555 - 558]

22
[ 38460-95-6 ]
[ 108-98-5 ]
[ 68117-63-5 ]

Yield	Reaction Conditions	Operation in experiment
92%	With triethylamine In toluene for 0.666667h;
92%	With triethylamine In toluene for 0.666667h;	Preparation of S-phenyl 10-undecenethioate (2) A 50-mL, one-necked, round-bottomed flask was charged with 10 mL toluene, triethylamine (0.70 mL, 5.0 mmol) and thiophenol (0.51 mL, 5.0 mmol). A solution of 10-undecenoyl chloride (1.10 mL, 5.1 mmol) in 15 mL toluene was added by a pressure-equalizing dropping funnel over 30 min while stirring the solution with a magnetic stirrer. Precipitating triethylammonium chloride made the reaction mixture turn to a turbid suspension. After 10 min of additional stirring the reaction was completed as monitored by TLC (iso-hexane/ethyl acetate 25:1, Rf=0.43). The organic mixture was washed twice with 25 mL saturated sodium hydrogen carbonate solution and once with 25 mL brine. The organic layer was dried over anhydrous MgSO4, filtered and the solvent evaporated in vacuo to yield 1.27 g (92%) S-phenyl 10-undecenethioate 2 as pale yellow oil. 1H NMR (300 MHz, CDCl3) δ 7.43 (app. S, 5H, C6H5), 5.83 (tdd, J=16.9, 10.2, 6.7 Hz, 1H, CH═CH2), 5.05-4.93 (m, 2H, CH═CH2), 2.67 (t, J=7.5 Hz, 2H, C(O)-CH2), 2.09-1.99 (m, 2H, CH2-CH═CH2), 1.73 (quint., J=7.5 Hz, 2H, CH2-CH2-C(O)), 1.44-1.29 (m, 10H, (CH2)5). 13C NMR (151 MHz, CDCl3) δ 197.8, 139.4, 134.7, 129.5, 129.4, 128.2, 114.4, 43.9, 34.0, 29.5, 29.4, 29.3, 29.2, 29.1, 25.8.
88%	With triethylamine In toluene for 0.333333h; Inert atmosphere;	4.1.2.1. S-Phenyl-10-undecene thioate (10) S-Phenyl-10-undecene thioate (10) was prepared as described before.7 To a stirring solution of thiophenol (1.02 mL, 10.0 mmol) and NEt3 (1.40 mL, 10.0 mmol) in toluene (20 mL) was added drop wise over 30 min a solution of 10-undecenoyl chloride (2.20 mL, 10.2 mmol) in toluene (30 mL). The reaction was monitored by TLC and was completed after 20 min. The mixture was then washed with saturated NaHCO3 solution (30 mL) and brine (10 mL), dried over MgSO4 and the solvent was removed under reduced pressure. Flash column chromatography on silica (iso-hexane/ethyl acetate 25:1) yielded 2.49 g (88%) of S-phenyl-10-undecene thioate (10) as colorless oil, Rf = 0.43. The spectral data are identical to those published previously.

With pyridine

Reference： [1]Boettcher, Thomas; Sieber, Stephan A. [Angewandte Chemie - International Edition, 2008, vol. 47, # 24, p. 4600 - 4603]
[2]Current Patent Assignee: TECHNICAL UNIVERSITY OF MUNICH - US9521845, 2016, B2 Location in patent: Page/Page column 37-38
[3]Location in patent: experimental part Zeiler, Evelyn; Korotkov, Vadim S.; Lorenz-Baath, Katrin; Böttcher, Thomas; Sieber, Stephan A. [Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 2, p. 583 - 591]
[4]Takai, Kazuhiko; Oshima, Koichiro; Nozaki, Hitosi [Bulletin of the Chemical Society of Japan, 1981, vol. 54, # 4, p. 1281 - 1282]

23
[ 38460-95-6 ]
[ 4316-73-8 ]
N-undecylenoyl sarcosine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 2433 - 2440

24
[ 38460-95-6 ]
[ 112-43-6 ]
[ 51964-84-2 ]

Yield	Reaction Conditions	Operation in experiment
95%
85%	With triethylamine In toluene at 0 - 25℃; for 3h; Inert atmosphere; Schlenk technique;
	With triethylamine In toluene at 20℃;

With pyridine In dichloromethane at 0 - 20℃; for 6h; Inert atmosphere;

Reference： [1]Fuerstner, Alois; Langemann, Klaus [Journal of Organic Chemistry, 1996, vol. 61, # 12, p. 3942 - 3943]
[2]Le, Duy; Samart, Chanatip; Kongparakul, Suwadee; Nomura, Kotohiro [RSC Advances, 2019, vol. 9, # 18, p. 10245 - 10252]
[3]Kowalczyk, Bartlomiej; Walker, David A.; Soh, Siowling; Grzybowski, Bartosz A. [Angewandte Chemie - International Edition, 2010, vol. 49, # 33, p. 5737 - 5741]
[4]Jee, Joo-Eun; Cheong, Jian Liang; Lim, Jaehong; Chen, Cheng; Hong, Soon Hyeok; Lee, Su Seong [Journal of Organic Chemistry, 2013, vol. 78, # 7, p. 3048 - 3056]

25
[ 38460-95-6 ]
[ CAS Unavailable ]
[ 175357-18-3 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; chloro-trimethyl-silane 1.) CH₂Cl₂, 2.) CH₂Cl₂; Yield given. Multistep reaction;

Reference： [1]Leydet; El Hachemi; Boyer; Lamaty; Roque; Schols; Snoeck; Andrei; Ikeda; Neyts; Reymen; Este; Witvrouw; De Clercq [Journal of Medicinal Chemistry, 1996, vol. 39, # 8, p. 1626 - 1634]

26
[ 38460-95-6 ]
[ 39243-54-4 ]

Yield	Reaction Conditions	Operation in experiment
80%	With bromine In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;	10, 11-Dibromoundecanoyl chloride (5-1) Br2 (16.00 g, 98.7 mmcl) was slowly added toa solution of lO-Undecenoyl chloride 4-1 (20.00 g,98.7 mmol) in of dry dichioromethane (50 ml) at 0°C.The mixture was stirred during 1 h at 0 °C and after that during additional 1 h at room temperature. After the evaporation of the solvent, the product was purified by vacuum distillation (1 mbar, 170 °C) to give pure compound 5-1 (28.62 g, 80%) as a colorless hg-uid.‘H NMR (250 MHz, CDC13) 6 4.17 (m, 1H), 3.86(dd, J = 10.1, 4.3 Hz, 1H), 3.63 (t, J = 10.1 Hz, 1H),2.90 (t, J = 7.3 Hz, 2H), 2.15 (m, lH), 1.29-1.88(overlapping peaks, 13H)‘3C NMR (75 MHz, CDC13) 6 173.76, 52.99,47.04, 36.27, 35.93, 29.00, 28.88, 28.60, 28.31,26.62, 24.98.Anal. calcd. for C,1H,9Br2C1O: C, 36.44; H,5.28; Br, 44.08, Cl, 9.78. Found: C, 36.70; H, 5.43;Br, 44.00; Cl, 9.68.
80%	With bromine In dichloromethane at 0 - 25℃; for 2h; Inert atmosphere;
	With bromine In tetrachloromethane for 0.25h; Ambient temperature;

Reference： [1]Current Patent Assignee: RUSSIAN ACADEMY OF SCIENCES; FEDERAL STATE UNITARY ENTERPRISE OF RUSSIAN FEDERATION; NOKIA OYJ - WO2016/64292, 2016, A1 Location in patent: Page/Page column 21; 25
[2]Borshchev; Sizov; Agina; Bessonov; Ponomarenko [Chemical Communications, 2017, vol. 53, # 5, p. 885 - 888]
[3]Malanga, Corrado; Mannucci, Serena; Lardicci, Luciano [Tetrahedron, 1998, vol. 54, # 7, p. 1021 - 1028]

27
[ 6281-32-9 ]
[ 38460-95-6 ]
[ 251922-69-7 ]

Reference： [1]Tetrahedron,2000,vol. 56,p. 2239 - 2246
[2]Tetrahedron Letters,1999,vol. 40,p. 7329 - 7332

28
[ 38460-95-6 ]
[ 811-98-3 ]
[ 774610-27-4 ]

Yield	Reaction Conditions	Operation in experiment
94%	With triethylamine In dichloromethane at 75℃; for 2h;

Reference： [1]Al-Abadleh, Hind A.; Voges, Andrea B.; Bertin, Paul A.; Nguyen, SonBinh T.; Geiger, Franz M. [Journal of the American Chemical Society, 2004, vol. 126, # 36, p. 11126 - 11127]

29
[ 38460-95-6 ]
[ 75-89-8 ]
10-undecenoic acid 2,2,2-trifluoroethanol ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With pyridine In benzene at 0 - 20℃;

Reference： [1]Sun, Qiao-Yu; De Smet, Louis C. P. M.; Van Lagen, Barend; Giesbers, Marcel; Thuene, Peter C.; Van Engelenburg, Johan; De Wolf, Frits A.; Zuilhof, Han; Sudhoelter, Ernst J. R. [Journal of the American Chemical Society, 2005, vol. 127, # 8, p. 2514 - 2523]

30
[ 38460-95-6 ]
[ 2578-33-8 ]
(R)-2-Undec-10-enoylamino-pentanedioic acid 5-benzyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 867 - 874

31
[ 38460-95-6 ]
[ 26081-03-8 ]
(S)-3-(undec-10-enoyl)amino-caprolactam [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With sodium carbonate; In dichloromethane; water; at 20℃; for 2.0h;	Example 3: (S)-3- (undec-10-enoyl) amino-caprolactam: (USD)-3-amino-caprolactam hydrochloride (2 mmol) and Na2CO3 (6 mmol) in water (25 ml) were added to a solution of undec-10-enoyl chloride (2 mmol) in dichloromethane (25 ml) at ambient temperature and the reaction mixture was stirred for 2 hours. The organic layer was then separated and the aqueous phase was extracted with additional dichloromethane (2 x 25 ml). The combined organic layers were dried over Na2CO3 and reduced in vacuo. The residue was purified by recrystallisation from EtOAc to give the title compound (423 mg; 72%). Melting point: 83-84 C. [a]" (c = 1, CHC'3) = +40. 1. IR: Vmax (cm-1): 3327,3273 (NH), 1655,1630 (CO), 1521 (NH). 'H NMR (No.H, 500 MHz, d6-DMSO) : 7.75 (1H, t, J6, CH2NH), 7.66 (1H, d, J7, CHNH), 5.76 (1H, ddt, J 17,10, 6.5 CH2=CH), 4.96 (1H, dq, J 17,2, CHH=CH, 4.96 (1H, ddt, J 17,2, 1, CHH=CH), 4. 36 6 (1H, dd, J 10, 7, CHNH), 3.14 (1H, ddd, J 15. 5,11. 5,5, CHHNH), 3.03 (1H, br dt, J 13, 5.5, CHHNH), 2.16-2. 06 (2H, m, CH2CONH), 1.98 (2H, br q, J7, CH2=CHCH2), 1. 85 (1H, dt, J 10.5, 3, C-5 H), 1.75-1. 67 (2H, m, C-4 H, C-6 H), 1.60 (1H, qt, J 13,3. 5, C-5 H), 1.44 (2H, br qn, J 7, CH2CH2CONH), 1.39-1. 27 (3H, m, CH2=CHCH2CH2 + C-4 H) and 1.31-1. 13 (9H, m, (CH2) 4 + C-6 H). 13C NMR (6c, 125 MHz, d6-DMSO) : 174.4 (CO-ring), 171.3 (CO-chain), 138.9 (CH2=CH), 114.7 (CH2=CH), 51.3 (NHCHCO), 40.7 (NCH2), 35.3, 33.3, 31.3, 29.0, 28.9 (x2) 28.7, 28.6, 28.4, 27. 8 and 25.4 (CH2). m/z (C3oN202Na) : 317.21970 (calculated: 317.2205).

Reference： [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 867 - 874
[2]Patent: WO2005/53702,2005,A2 .Location in patent: Page/Page column 17-18

32
[ 38460-95-6 ]
[ 76-05-1 ]
[ 85657-91-6 ]

Yield	Reaction Conditions	Operation in experiment
63%	Stage #1: undec-10-enoyl chloride With sodium azide; tetrabutylammomium bromide In dichloromethane at 0℃; for 3h; Stage #2: trifluoroacetic acid In dichloromethane Heating;

Reference： [1]Kaur, Navneet; Delcros, Jean-Guy; Martin, Bénédicte; Phanstiel IV, Otto [Journal of Medicinal Chemistry, 2005, vol. 48, # 11, p. 3832 - 3839]

33
[ 38460-95-6 ]
[ 103898-11-9 ]
tert-butyl N-(2-hydroxyethyl)-N-[2-(10-undecenoyloxy)ethyl]carbamate [ No CAS ]

Reference： [1]Chemistry Letters,2007,vol. 36,p. 1196 - 1197

34
[ 38460-95-6 ]
[ 85657-91-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: NaN₃ / tetrabutylammonium bromide / CH₂Cl₂; H₂O / 2 h / 0 °C 2: CH₂Cl₂ / 11 h / Heating

Reference： [1]Pfister, Juerg R.; Wymann, Walter E. [Synthesis, 1983, # 1, p. 38 - 40]

35
[ 38460-95-6 ]
[ 4767-03-7 ]
[ 511529-53-6 ]

Yield	Reaction Conditions	Operation in experiment
72%	With pyridine for 10h;	1 The intermediate Compound (9) was prepared as follows. a. Compound (8). bis (Hydroxymethyl) propionic acid (DMPA, 2. [0 G,] 15 mmol) was dissolved into pyridine (25 ml). After 10 minutes flushing with nitrogen in ice/water bath, 10-undecenoyl chloride (7.4 ml, 34 mmol) was added dropwise. After 10 hours, the reaction mixture was poured into 0.1 N [HC1] solutions (300 ml) and stirred for 10 minutes. Ethyl ether (100 ml) was used to extract the product. The extraction was washed with 50 ml portions of brine [(5),] dried over anhydrous sodium sulfate, and evaporated to dryness. The crude product was purified by chromatography using petroleum ether: ethyl acetate (80: 20) as eluent. Compound (9) was obtained as a colorless oil (5.0 g), yield: [72%.]

Reference： [1]Current Patent Assignee: RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY - WO2003/103594, 2003, A2 Location in patent: Page 17

36
[ 38460-95-6 ]
[ 456-64-4 ]
C₁₈H₂₄F₃NO₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20℃;	Example 3 Preparation of; A solution of N-phenyltrifluoromethylsulfonamide (2.2 g) and N,N-diisopropylethylamine (1.3 g) in dry THF (25 mL) is added to a stirred solution of 10-undecenoyl chloride (2.0 g) in dry THF (25 mL). The solution is stirred overnight at room temperature and then the volatile components are removed using a rotary evaporator and then a high vacuum pump. A solution of this material is then made in methylene chloride (30 g) in 125 mL screw cap bottle. Platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisilane complex in xylenes is diluted with methylene chloride to a concentration of approximately 1.5 weight percent, and 3 drops of this solution are added to the bottle. The bottle is then sealed and is heated to 60 C. in a water bath. After 18 hours, the mixture is allowed to cool to room temperature and additional platinum complex solution (1 drop) is added. The bottle is again sealed and is heated at 60 C. for an additional 24 hours. The mixture is then cooled to room temperature and the volatile components are removed using a rotary evaporator to afford the product.

Reference： [1]Patent: US2005/107615,2005,A1 .Location in patent: Page/Page column 19

37
[ 3325-11-9 ]
[ 38460-95-6 ]
6(octadeca-9,12-dienoylamino)-2-mercaptobenzothiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		2.68 Parts of <strong>[3325-11-9]5-aminobenzotriazole</strong> (prepared as described in U..S. Pat. No. 4,428,987) were reacted with 7.5 parts of undec-10-enoyl chloride (prepared as described in part A), using the procedure described in Example 4 for the preparation of 6(octadec-9,12-dienoylamino)-2-mercaptobenzothiazole. The product (4.5 parts, melting point 189°-191° C., 73.3percent yield) was found by analysis to contain C 66.5percent wt; H 8.4percent wt; and N 17.8percent wt. 5(undec-10-enoylamino)-benzotriazole (C17 H24 N4 O) requires C 68percent wt; H 8.0percent wt; and N 18.7percent wt.

Reference： [1]Patent: US4978756,1990,A

38
magnesium sulfate anhydride [ No CAS ]
[ 821-09-0 ]
[ 38460-95-6 ]
[ 76293-71-5 ]

Yield	Reaction Conditions	Operation in experiment
86.4%	With pyridine; hydrogenchloride In dichloromethane	28.1 (1) (1) Synthesis of 4-pentenyl 10-undecenoate A flask was charged with 10 g (116 mmol) of 4-pentenol, 200 ml of methylene chloride, 18.33 g (232 mmol) of pyridine and the mixture was ice-cooled. To the mixture was added dropwise 80 ml of a methylene chloride solution containing 23.51 g (116 mmol) of 10-undecenoyl chloride. The resulting mixture was stirred for 30 minutes and then at room temperature for 3 hours. The insoluble substance was filtered. 5% hydrochloric acid was added to the filtrate to separate an organic layer. The organic layer was washed with an aqueous saturated sodium bicarbonate solution and water in this order, followed by drying using magnesium sulfate anhydride. After the drying, a solvent was distilled and the residue was subjected to vacuum distillation (121-123° C./2 mmHg) to obtain 25.3 g of an object material in a yield of 86.4%. The result of 1H-NMR(CDCl3) of the above reaction solution is as follows: 1H-NMR(CDCl3) δ: 1.29-1.39(m, 10H), 1.58-1.64 (m, 2H), 1.69-1.76(m, 2H), 2.01-2.07(m, 2H), 2.09-2.15(m, 2H), 2.29(t, 2H), 4.08(t, 2H), 4.91-5.06(m, 4H), 5.76-5.86(m, 2H)

Reference： [1]Current Patent Assignee: TAKASAGO INTERNATIONAL CORPORATION - US6175047, 2001, B1

39
[ 2103-99-3 ]
[ 38460-95-6 ]
[ 86306-46-9 ]

Yield	Reaction Conditions	Operation in experiment
98%	With pyridine In 1,4-dioxane for 1.5h; Heating / reflux;	2.4 Compound 4. Undec-10-enoic acid [4-(4-chloro-phenyl)-thiazol-2-yl]-amide (B231205) 10-undecenoyl chloride (47 mg, 0.23 mmol) was placed in a dried 100 mL round bottom reaction flask by syringe Anhydrous dioxane (5 mL) was added to it, followed by addition of 2-amino-4-(4-chlorophenyl)thiazol (50 mg, 0.23 mmol) and pyridine (100 uL). The mixture was heated under reflux for 1.5 h. After cooling to RT and removal of the solvent, the residue was dissolved in dichloromethane (50 mL) and washed with water (50 mL). The organic solution was dried over sodium sulfate. After filtration through a pad of silica eluted with chloroform, the concentrated residue was purified by chromatotron (silica, chloroform) to afford a white solid (85 mg, 0.225 mmol). Rf=0.35 (chloroform, silica). Y=98%. NMR and MS confirmed it is the target compound

Reference： [1]Current Patent Assignee: APOGEE BIOTECHNOLOGY CORPORATION - US2007/32531, 2007, A1 Location in patent: Page/Page column 32

40
[ 61-80-3 ]
[ 38460-95-6 ]
[ 924624-28-2 ]

Yield	Reaction Conditions	Operation in experiment
33%	With triethylamine; In benzene; at 20℃; for 2.5h;Heating / reflux;	Compound 90. Undec-10-enoic acid (5-chloro-benzooxazol-2-yl)-amide (B231117) 10-Undecenoyl chloride (120 mg, 0.59 mmol) was placed in a dried 100 mL round bottom reaction flask by syringe. Anhydrous benzene (5 mL) was added to it, followed by addition of 2-amino-5--chlorobenzoxazole (100 mg, 0.59 mmol) and TEA (100 uL). The mixture was stirred at RT for 0.5 hi It was then heated under reflux for 2 h. After cooling to RT and removal of the solvent, the residue was crystallized in ethanol to afford a white powder solid (65 mg, 0.19 mmol). Y=33%. NMR and MS confirmed it is the target compound.

Reference： [1]Patent: US2007/32531,2007,A1 .Location in patent: Page/Page column 48

41
[ 38460-95-6 ]
[ 1134-47-0 ]
[ 1073838-95-5 ]

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

42
[ 38460-95-6 ]
[ 2050-14-8 ]
[ 1186466-39-6 ]

Reference： [1]Tetrahedron,2009,vol. 65,p. 6959 - 6964

43
[ 38460-95-6 ]
[ 168297-85-6 ]
[ 1207362-39-7 ]

Reference： [1]Journal of the American Chemical Society,2010,vol. 132,p. 1482 - 1483

44
[ 38460-95-6 ]
[ 58574-03-1 ]
[ 133641-67-5 ]

Yield	Reaction Conditions	Operation in experiment
92%	With triethylamine In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;
90%	With triethylamine In tetrahydrofuran at 20℃; for 12h; Inert atmosphere;	4-[4'-(10-Decenylcarbonyloxy)phenyl]benzoicacid (3) 4-(4-Hydroxyphenyl)benzoic acid (5 g, 0.023 mol) was dissolved in dry THF (20 mL),and dry TEA (2.7 g, 0.0276 mol) was added under nitrogen atmosphere. Freshly prepared 10-undecenoylchloride(2) (5.59g,0.0276mol)wasmixedwith5mLofdryTHFandaddeddropwise to the reaction mixture and was stirred continuously for 12 h at ambient tempera-ture. The precipitated amine hydrochloride was filtere dof f,a ndT HFw asevaporat ed todry-nessunderreducedpressure.Awhitesolidobtainedwasrecrystallizedwithabsoluteethanolto yield 3 (7.5 g, 90%) . 1H NMR (CDCl3, δ): 4.8-5.1 Hz (m, 2H, CH2), 5.8-5.9 Hz (m, 1H,CH), 2.0-2.1 Hz (m, 2H, CH2), 1.3-1.5 Hz (m, 10H, CH2), 1.7-1.8 Hz (m, 2H, CH2CH2),2.5-2.6 Hz (t, 2H, CO-CH2), 7.1-8.3 Hz (m, 8H, Ar- H).

Reference： [1]Location in patent: experimental part Balamurugan; Kannan [Journal of Molecular Structure, 2009, vol. 934, # 1-3, p. 44 - 52]
[2]Viswanath, Lakshmi C. Kasi; Senthil, Sengodan [Molecular Crystals and Liquid Crystals, 2017, vol. 656, # 1, p. 12 - 21]

45
[ 38460-95-6 ]
[ 1155-64-2 ]
[ 1246518-38-6 ]

Yield	Reaction Conditions	Operation in experiment
81%	Stage #1: undec-10-enoyl chloride; N₆-[(benzyloxy)carbonyl]-L-lysine With sodium hydroxide In water at 20℃; for 1h; Stage #2: With hydrogenchloride In water

Reference： [1]Kowalczyk, Bartlomiej; Walker, David A.; Soh, Siowling; Grzybowski, Bartosz A. [Angewandte Chemie - International Edition, 2010, vol. 49, # 33, p. 5737 - 5741]

46
[ 100-02-7 ]
[ 38460-95-6 ]
[ 151309-96-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With pyridine In diethyl ether for 2h; Reflux;	4.a.1 Synthesis of 4-nitrophenylundec-1 -eneester Added to a solution of 4-nitrophenol (3.25 g; 23 mmol; 1 eq.) dissolved in 50 ml of anhydrous ether, was pyridine (1.85 g; 1.9 ml; 23 mmol; 1 eq.). The solution was heated under reflux of ether and undecenoyl chloride (97%) (4.9 g; 5.2 ml; 23 mmol; 1 eq.) was added very slowly (over a period of around 1 hour). The reaction was continued under reflux of ether for 1 hout The reaction mixture was filtered, then the filtrate was concentrated to give a yellowish liquid.The characteristics of the product obtained were the following:Mass obtained: 7.1 gYield: 100%‘H NMR (200 MHz; CDC13): 1.33 (bR; m; H’°-’j; 1.74(2H; m; H9); 2.04 (2H; m; H’5); 2.60 (2H; t; H8);Hz); 4.98 (2H; m; H’7); 5.80 (1H; m; H’6); 7.27 (2H; d;H35 3JH_H=9.2 Hz); 8.27 (2H; d; H26 3JH_H=9.2 Hz)‘3C NMR (200 MHz; CDC13): 25.13; 29.28; 29.43 (2C);29.56; 29.66; 34.17; 34.73; 114.61 (C’7); 122.84 (2C; C35)125.59 (2C; C26); 139.52 (C’6); 145.66 (C’) 155.96 (C4);171.73 (C7).
87%	With potassium hydroxide In water at 5℃;

Reference： [1]Current Patent Assignee: COMMISSARIAT A L'ENERGIE ATOMIQUE ET AUX ENERGIES ALTERNATIVES - US9657042, 2017, B2 Location in patent: Page/Page column 19
[2]Location in patent: experimental part Nielsen, Anne L.; Steffensen, Kim; Wimmer, Reinhard; Worm-Leonhard, Martin; Larsen, Kim L. [Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2010, vol. 67, # 3, p. 303 - 315]

47
[ 2637-34-5 ]
[ 38460-95-6 ]
[ 134781-63-8 ]

Yield	Reaction Conditions	Operation in experiment
92%	With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	4.1.2.3. S-Pyridin-2-yl-10-undecene thioate (7) To a stirred solution of 2-pyridylmercaptane (6.6 g, 60 mmol) in CH2Cl2 (150 mL) was added 10-undecenoyl chloride (10 g, 50 mmol) at 0 °C followed by Et3N (15 mL, 108 mmol). The solution was stirred for 2 h at rt, quenched with 1 N HCl, phases were separated and the organic phase was washed with saturated NaHCO3 solution and then dried over Na2SO4. Volatiles were removed under reduced pressure yielding a yellow oil that was purified by flash column chromatography (hexane/ethyl acetate 2:1, Rf = 0.76). Yield: 12.7 g (92%). 1H NMR (360 MHz, CDCl3) δ 8.62-8.65 (m, 1H, pyridine), 7.72-7.78 (m, 1H, pyridine), 7.61-7.65 (m, 1H, pyridine), 7.20 (ddd, J = 5, 7, 1 Hz, 1H, pyridine), 5.76-5.89 (m, 1H, CHCH2), 4.92-5.05 (m, 2H, CH2CH), 2.71 (t, J = 7 Hz, 2H, CH2), 2.00 2.09 (m, 2H, CH2), 1.68-1.79 (m, 2H, CH2), 1.25-1.45 (m, 10H, (CH2)5). 13C NMR (91 MHz, CDCl3): 196.59, 151.73, 150.39, 139.15, 137.04, 130.09, 123.40, 114.17, 44.24, 33.77, 29.21, 29.17, 29.02, 28.91, 28.89, 25.41. IR (film) ν = 2925 cm-1, 2855, 1627, 1575, 1560, 1449, 1417, 1253, 1081, 838, 783. MS (ESI) positive ion mode: m/z = 278 ([M+H]+, 100%). HRMS (ESI) calcd for C16H24NOS [M+H]+ 278.1579, found 278.1564.
40%	Stage #1: 2-Sulfanylpyridine With triethylamine In tetrahydrofuran at 0℃; for 0.25h; Stage #2: undec-10-enoyl chloride In tetrahydrofuran	24 A solution of triethylamine (2.5 mL), THF (20 mL) and 2-mercaptopyridine (0.77 g, 6.95 mmol) was stirred for 15 minutes at 0 °C. A solution of undec-10-enoyl chloride (X) (1.17 g, 5.79 mmol) in THF (20 mL) was added all at once. Immediately the reaction was then quenched by adding an aqueous HCl-solution (2.0 M, 50 mL) at 0°C and subsequently extracted with diethyl ether. The organic phase was separated and the aqueous phase was extracted with diethylether. The combined organic phases were washed with a saturated bicarbonate solution and brine, dried over MgSO4 and evaporated under reduced pressure to give a yellow oil. The crude green oil was purified by column chromatography using silica gel (eluent CH2Cl2). The compound (XI) was obtained as a lightly yellow oil. (0.64 g, 40 %).

Reference： [1]Location in patent: experimental part Zeiler, Evelyn; Korotkov, Vadim S.; Lorenz-Baath, Katrin; Böttcher, Thomas; Sieber, Stephan A. [Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 2, p. 583 - 591]
[2]Current Patent Assignee: INSTITUT DE MICRO-ÉLECTRONIQUE ET COMPOSANTS (IMEC); HASSELT UNIVERSITY - EP2397475, 2011, A1 Location in patent: Page/Page column 47

48
[ 38460-95-6 ]
[ 1435-55-8 ]
[ 130285-25-5 ]

Reference： [1]European Journal of Organic Chemistry,2012,p. 1336 - 1345

49
[ 38460-95-6 ]
[ 1711-24-6 ]
[ 864498-64-6 ]

Reference： [1]Journal of Polymer Science, Part A: Polymer Chemistry,2012,vol. 50,p. 5049 - 5059

50
[ 38460-95-6 ]
[ 6038-19-3 ]
[ 1509857-80-0 ]

Reference： [1]Macromolecules,2014,vol. 47,p. 61 - 69

51
[ 38460-95-6 ]
[ 2199-43-1 ]
[ 1610043-21-4 ]

Yield	Reaction Conditions	Operation in experiment
53%	With ytterbium(III) triflate In nitromethane at 20℃; for 21h;	2 Friedel-Craf s acylation: To the respective acid chloride (2 equiv.) in nitromethane (6 mL / 1 g of acid chloride) was added the respective pyrrole (1 equiv.) followed by the addition of ytterbium (III) trifluoromethanesulfonate (0.1 equiv.). The resulting dark red solution was stirred at ambient temperature for 21 h. The reaction was quenched by addition of saturated aqueous NaHC03 and the mixture was extracted with diethyl ether (3x). The organic layers were combined, washed with saturated aqueous NaHC03, H20 (2x), brine, dried over MgS04 and volatiles were removed in vacuo and the resultant crude oil was purified via flash chromatography to give the desired pure pyrroles.
53%	With ytterbium(III) triflate In nitromethane at 20℃; for 21h;

Reference： [1]Current Patent Assignee: UNIVERSITY OF ADELAIDE - WO2014/75146, 2014, A1 Location in patent: Paragraph 00222; 00223
[2]Chua, Krystle C. H.; Pietsch, Markus; Zhang, Xiaozhou; Hautmann, Stephanie; Chan, Hon Y.; Bruning, John B.; Guetschow, Michael; Abell, Andrew D. [Angewandte Chemie - International Edition, 2014, vol. 53, # 30, p. 7828 - 7831][Angew. Chem., 2014, vol. 126, # 30, p. 7962 - 7965,4]

52
[ 38460-95-6 ]
[ 32112-13-3 ]
UndDHexdA [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91.3%	With triethylamine In tetrahydrofuran at 20℃; for 2h;
91.3%	With triethylamine In tetrahydrofuran at 20℃; for 2h;	4.1 1. Amidation reaction - preparation of a compound of formula (III): To SebHex-diamine (8.4 g, 25 mmol), dried THF (100 mL) and triethylamine (5.5 g, 55 mmol, 1.1 eq.) were added. Then undecenyl chloride (10 g, 49 mmol) was added dropwise. The reaction mixture was then stired at room temperature for 2 hours. UndDHexdA was purified by filtration of the formed salt, followed by column chromatography to eliminate completely the monoamide (eluent: heptane / ethyl acetate (95/5)). Yield = 91.3%. [0072] The compound UndHexa is obtained: [0073] UndDHexdA: 1H NMR (CDCl3, 50°C, 400 MHz) δ (ppm): 5.80 (m, 2H), 4.94 (m, 4H), 3.27 (m, 4H), 3.19 (m, 4H), 2.27 (t, 4H), 2.02 (m, 4H), 1.62 (m, 4H), 1.51 (m, 8H), 1.36-1.28 (m, 40H), 0.88 (m, 6H). IR (cm-1): 2924, 2851, 1642, 906.
91.3%	With triethylamine In tetrahydrofuran at 20℃; for 2h;	4.1 1 . Amidation reaction - preparation of a compound of formula (III): To SebHex-diamine (8.4 g, 25 mmol), dried THF (100 ml_) and triethylamine (5.5 g, 55 mmol, 1 .1 eq.) were added. Then undecenyl chloride (10 g, 49 mmol) was added dropwise. The reaction mixture was then stired at room temperature for 2 hours. UndDHexdA was purified by filtration of the formed salt, followed by column chromatography to eliminate completely the monoamide (eluent: heptane / ethyl acetate (95/5)). Yield = 91 .3%. The compound UndHexa is obtained: UndDHexdA: 1 H NMR (CDCI3, 50°C, 400 MHz) δ (ppm): 5.80 (m, 2H), 4.94 (m, 4H), 3.27 (m, 4H), 3.19 (m, 4H), 2.27 (t, 4H), 2.02 (m, 4H), 1 .62 (m, 4H), 1 .51 (m, 8H), 1 .36-1 .28 (m, 40H), 0.88 (m, 6H). IR (cm 1): 2924, 2851 , 1642, 906.

Reference： [1]Maisonneuve, Lise; More, Arvind S.; Foltran, Stephanie; Alfos, Carine; Robert, Frederic; Landais, Yannick; Tassaing, Thierry; Grau, Etienne; Cramail, Henri [RSC Advances, 2014, vol. 4, # 49, p. 25795 - 25803]
[2]Current Patent Assignee: INSTITUT DES CORPS GRAS ETUDES ET RECHERCHES TECHN; UNIVERSITY OF BORDEAUX 1; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; INSTITUT POLYTECHNIQUE DE BORDEAUX - EP2883872, 2015, A1 Location in patent: Paragraph 0068-0073
[3]Current Patent Assignee: INSTITUT DES CORPS GRAS ETUDES ET RECHERCHES TECHN; UNIVERSITY OF BORDEAUX 1; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; INSTITUT POLYTECHNIQUE DE BORDEAUX - WO2015/91494, 2015, A1 Location in patent: Page/Page column 16-17

53
[ 824935-09-3 ]
[ 38460-95-6 ]
[ 1621607-97-3 ]

Yield	Reaction Conditions	Operation in experiment
71%	With triethylamine In dichloromethane at 20℃; for 2h; Inert atmosphere; Cooling with ice;	2 4.1. General method for the synthesis of N'-alkyl/aryl/heteroaryl-4-(tricyclo[3.3.1.1^3,7]dec-1-yl)quinoline-2-carbohydrazides (3-17) General procedure: To the ice-cold solution of 2 (10 mmol) and Et3N (20 mmol) in dry CH2Cl2 (10 mL), alkyl/aryl/heteroaryl acid chloride (12 mmol) was added slowly under N2 atmosphere. The ice bath was removed and the reaction was allowed to proceed at ambient temperature for 2 h. The reaction mixture was poured onto crushed ice and extracted with CH2Cl2 (3 x 25 mL). The combined organic extract was washed with brine (20 mL), dried over sodium sulfate and evaporated under reduced pressure to afford carbohydrazide derivatives 3-17, which were purified through flash column chromatography using EtOAc/hexanes as mobile phase.

Reference： [1]Patel, Sanjay R.; Gangwal, Rahul; Sangamwar, Abhay T.; Jain, Rahul [European Journal of Medicinal Chemistry, 2014, vol. 85, p. 255 - 267]

54
cellulose acetate propionate [ No CAS ]
[ 38460-95-6 ]
cellulose acetate propionate undec-10-enoate, degree of substitution undec-10-enoate 0.51 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94.2%	With triethylamine In butanone at 60℃; for 20h; Inert atmosphere;	Preparation of Cellulose Acetate Propionate Undec-10-enoate. General procedure: Preparation of Cellulose Acetate Propionate Undec-10-enoate. CAP-504-0.2 (1.00 g, 1.78 mmol/AGU) was dissolved in MEK (20 mL), and the solution was heated to 60 °C with magnetic stirring under N2. After the addition of triethylamine (0.54 mL, 1.96 mmol, 1.1 equiv.), undec-10-enoyl chloride (0.72 g, 3.56 mmol, 1.0 equiv.) was added dropwise, and the mixture was stirred for 20 h at 60 °C. After filtration to remove triethylammonium chloride, the filtrate was precipitated into 300 mL 50:50 water/ethyl alcohol. Product was redissolved in CH2CI2, reprecipitated in hexane and dried under vacuum at 40 °C. Cellulose Acetate Propionate Undec-10-enoate. l NMR (CDC13): 0.99-1.18 (m, COCH2CH3), 1.27- 1.35 (m, COCH2CH2CH2CH2CH2CH2CH2CH2CH=CH2), 1.55- 1.63 (m, COCH2CH2CH2CH2CH2CH2CHiCH2CH=CH2), 2.01 (m, COCH2CH2CH2CH2CH2CH2CH2CH2CH=CH2), 2.15-2.36 (m, COCH3, COCH2CH3, and COCH2CH2CH2CH2CH2CH2CH2CH2CH=CH2), 3.25-5.24 (m, cellulose backbone), 4.89-4.99 (q, COCH2CH2CH2CH2CH2CH2CH2CH2CH=CH2), 5.78 (m, COCH2CH2CH2CH2CH2CH2CH CH2CH=CH2) . DS by 1H NMR: undec-10-enoate 0.51. Yield: 94.2%.

Reference： [1]Current Patent Assignee: VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY - WO2015/48408, 2015, A1 Location in patent: Paragraph 00082-00094

55
[ 38460-95-6 ]
Cellulose acetate [ No CAS ]
cellulose acetate undec-10-enoate, degrees of substitution undec-10-enoate 0.67, acetate 1.73 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93.6%	With triethylamine at 90℃; for 20h; Inert atmosphere;	Preparation of Cellulose Acetate Undec-10-enoate. Preparation of Cellulose Acetate Undec-10-enoate. CA-320S ( 1.00 g, 4.19 mmol/AGU) was dissolved in DMI (30 mL), and the solution was heated to 90 °C with mechanical stirring under N2. Triethylamine (1.29 mL, 9.22 mmol, 2.2 equiv.; or 3.20 mL, 23.0 mmol, 5.5 equiv.) was added; a condenser was used to avoid evaporative loss of the base catalyst. Undec-10-enoyl chloride (1.70 g, 8.36 mmol, 2.0 equiv.; or 4.25 g, 20.95 mmol, 5.0 equiv.) was added dropwise and allowed to react at 90 °C for 20 h. The reaction mixture was then filtered, and the filtrate was precipitated in 300 mL 50:50 water/ethyl alcohol. The precipitate was redissolved in a minimal amount of CH2CI2 and reprecipitated in hexane. The product was washed with hexane and dried under vacuum at 40 °C. 1H NMR (CDCI3): 1.22 (br s, COCH2CH2CH2CH2CH2CH2CH2CH2CH=CH2), 1.33 (br s, COCH2CH2CH2CH2CH2CH2CH2CH2CH=CH2), 1.53 (br s, COCH2CH2CH2CH2CH2CH2CH2CH2CH=CH2), 1.88-2.03(m, COCH2CH2CH2CH2CH2CH2CH2CH2CH=CH2 and COCH3), 2.26 (br s, COCH2CH2CH2CH2CH2CH2CH2CH2CH=CH2), 3.25-5.24 (m, cellulose backbone), 4.85-4.94 (q, COCH2CH2CH2CH2CH2CH2CH2CH2CH=CH2), 5.75 (m, o 13 COCH2CH2CH2CH2CH2CH2CH2CH2CH=CH2). 13C NMR (CDC13): 20.4 (COCH3), 24.8 (COCH2CH2CH2CH2CH2CH2CH2CH2CH=CH2), 28.8 (COCH2CH2CH2CH2CH2CH2CH2CH2CH=CH2), 33.6 (COCH2CH2CH2CH2CH2CH2CH2CH2CH=CH2), 114.1 (COCH2CH2CH2CH2CH2CH2CH2CH2CH=CH2), 139.0 (COCH2CH2CH2CH2CH2CH2CH2CH2CH=CH2), 168.9-173.1 (C=0), 62.2 (C-6), 72.0-76.4 (C2, C3, C5), 82.3 (C-4), 100.7 (C-I). For the batch with 2.0 equivalents/ AGU undec-10-enoyl chloride, degrees of substitution (DS) by lU NMR: undec-10-enoate 0.67, acetate 1.73; yield: 93.6%. For the batch with 5.0 equivalents/AGU undec-10-enoyl chloride, DS by lH NMR: undec-10-enoate 1.28, acetate 1.73; yield: 90.7%.

Reference： [1]Current Patent Assignee: VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY - WO2015/48408, 2015, A1 Location in patent: Paragraph 00059-00081

56
[ 38460-95-6 ]
Cellulose acetate [ No CAS ]
cellulose acetate undec-10-enoate, degrees of substitution undec-10-enoate 1.28, acetate 1.73 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90.7%	With triethylamine at 90℃; for 20h; Inert atmosphere;	Preparation of Cellulose Acetate Undec-10-enoate. Preparation of Cellulose Acetate Undec-10-enoate. CA-320S ( 1.00 g, 4.19 mmol/AGU) was dissolved in DMI (30 mL), and the solution was heated to 90 °C with mechanical stirring under N2. Triethylamine (1.29 mL, 9.22 mmol, 2.2 equiv.; or 3.20 mL, 23.0 mmol, 5.5 equiv.) was added; a condenser was used to avoid evaporative loss of the base catalyst. Undec-10-enoyl chloride (1.70 g, 8.36 mmol, 2.0 equiv.; or 4.25 g, 20.95 mmol, 5.0 equiv.) was added dropwise and allowed to react at 90 °C for 20 h. The reaction mixture was then filtered, and the filtrate was precipitated in 300 mL 50:50 water/ethyl alcohol. The precipitate was redissolved in a minimal amount of CH2CI2 and reprecipitated in hexane. The product was washed with hexane and dried under vacuum at 40 °C. 1H NMR (CDCI3): 1.22 (br s, COCH2CH2CH2CH2CH2CH2CH2CH2CH=CH2), 1.33 (br s, COCH2CH2CH2CH2CH2CH2CH2CH2CH=CH2), 1.53 (br s, COCH2CH2CH2CH2CH2CH2CH2CH2CH=CH2), 1.88-2.03(m, COCH2CH2CH2CH2CH2CH2CH2CH2CH=CH2 and COCH3), 2.26 (br s, COCH2CH2CH2CH2CH2CH2CH2CH2CH=CH2), 3.25-5.24 (m, cellulose backbone), 4.85-4.94 (q, COCH2CH2CH2CH2CH2CH2CH2CH2CH=CH2), 5.75 (m, o 13 COCH2CH2CH2CH2CH2CH2CH2CH2CH=CH2). 13C NMR (CDC13): 20.4 (COCH3), 24.8 (COCH2CH2CH2CH2CH2CH2CH2CH2CH=CH2), 28.8 (COCH2CH2CH2CH2CH2CH2CH2CH2CH=CH2), 33.6 (COCH2CH2CH2CH2CH2CH2CH2CH2CH=CH2), 114.1 (COCH2CH2CH2CH2CH2CH2CH2CH2CH=CH2), 139.0 (COCH2CH2CH2CH2CH2CH2CH2CH2CH=CH2), 168.9-173.1 (C=0), 62.2 (C-6), 72.0-76.4 (C2, C3, C5), 82.3 (C-4), 100.7 (C-I). For the batch with 2.0 equivalents/ AGU undec-10-enoyl chloride, degrees of substitution (DS) by lU NMR: undec-10-enoate 0.67, acetate 1.73; yield: 93.6%. For the batch with 5.0 equivalents/AGU undec-10-enoyl chloride, DS by lH NMR: undec-10-enoate 1.28, acetate 1.73; yield: 90.7%.

Reference： [1]Current Patent Assignee: VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY - WO2015/48408, 2015, A1 Location in patent: Paragraph 00059-00081

57
[ 38460-95-6 ]
Cellulose acetate [ No CAS ]
cellulose acetate undec-10-enoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With 1,3-dimethyl-2-imidazolidinone; triethylamine at 90℃; for 20h; Inert atmosphere;	1 (1) Example procedure of the synthesis of cellulose acetate undec-10-enoate (1, CA-Un067) Cellulose acetate (CA-320S, 1.00 g, 4.19 mmol AGU) was dissolved in DMI (30 mL), and the solution was heated to 90 °C with mechanical stirring under N2. Triethylamine (1.29 mL, 9.22 mmol, 2.2 eq/AGU) was added. A condenser was used to avoid evaporative loss of the base catalyst. Undec-10-enoyl chloride (1.70 g, 8.36 mmol, 2.0 eq/AGU) was added dropwise and allowed to react at 90 °C for 20 h. The reaction mixture was then cooled to room temperature, filtered, and the filtrate was precipitated in 300 mL of a 50:50 v/v water-ethyl alcohol solution. The precipitate was redissolved in a minimal amount of CH2Cl2 (∼5 mL) and reprecipitated in hexane (∼100 mL). The product was washed with hexane and dried under vacuum at 40 °C (yield: 1.30 g, 95%, white powder).

Reference： [1]Meng, Xiangtao; York, Emily A.; Liu, Shu; Edgar, Kevin J. [Carbohydrate Polymers, 2015, vol. 133, p. 262 - 269]

58
cellulose acetate propionate [ No CAS ]
[ 38460-95-6 ]
cellulose acetate propionate undec-10-enoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With triethylamine In butanone at 60℃; for 20h; Inert atmosphere;	2 (2) Example procedure for the synthesis of cellulose acetate propionate undec-10-enoate (3, CAP-Un057). Cellulose acetate propionate (CAP-504-0.2, 1.00 g, 1.78 mmol AGU) was dissolved in MEK (20 mL), and the solution was heated to 60 °C with magnetic stirring under N2. After the addition of triethylamine (1.08 mL, 3.92 mmol, 2.2 eq/AGU), undec-10-enoyl chloride (1.44 g, 7.12 mmol, 2.0 eq/AGU) was added dropwise, and the mixture was stirred for 20 h at 60 °C. After cooling to room temperature, followed by filtration to remove triethylammonium chloride, the filtrate was precipitated into 300 mL of a 50:50 v/v water/ethyl alcohol solution. The product was redissolved in 20 mL of CH2Cl2, reprecipitated in 200 mL of hexane, and dried under vacuum at 40 °C (yield: 1.16 g, 86%, white powder).

Reference： [1]Meng, Xiangtao; York, Emily A.; Liu, Shu; Edgar, Kevin J. [Carbohydrate Polymers, 2015, vol. 133, p. 262 - 269]

59
cellulose acetate butyrate [ No CAS ]
[ 38460-95-6 ]
cellulose acetate butyrate undec-10-enoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With triethylamine In butanone at 60℃; for 20h; Inert atmosphere;	2 (2) Example procedure for the synthesis of cellulose acetate propionate undec-10-enoate (3, CAP-Un057). General procedure: Cellulose acetate propionate (CAP-504-0.2, 1.00 g, 1.78 mmol AGU) was dissolved in MEK (20 mL), and the solution was heated to 60 °C with magnetic stirring under N2. After the addition of triethylamine (1.08 mL, 3.92 mmol, 2.2 eq/AGU), undec-10-enoyl chloride (1.44 g, 7.12 mmol, 2.0 eq/AGU) was added dropwise, and the mixture was stirred for 20 h at 60 °C. After cooling to room temperature, followed by filtration to remove triethylammonium chloride, the filtrate was precipitated into 300 mL of a 50:50 v/v water/ethyl alcohol solution. The product was redissolved in 20 mL of CH2Cl2, reprecipitated in 200 mL of hexane, and dried under vacuum at 40 °C (yield: 1.16 g, 86%, white powder).

Reference： [1]Meng, Xiangtao; York, Emily A.; Liu, Shu; Edgar, Kevin J. [Carbohydrate Polymers, 2015, vol. 133, p. 262 - 269]

60
[ 38460-95-6 ]
[ 91188-89-5 ]
ethyl 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(undec-10-enamido)quinoline-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With triethylamine In dichloromethane at 20℃; for 12h;	General procedure for the synthesis of target compounds (8a-h): General Procedure General procedure: To a stirred solution of ethyl-7-amino-1-ethyl-6-fluoro-4-oxo-1, 4-dihydroquinoline-3-carboxylate (100 mg, 2 mmol) in DCM (5 mL), triethyl amine (0.1 mL) followed by acid chloride (1 mL) were added. Then the reaction mixture was stirred at RT for 12 h. The progress of reaction was monitored by TLC with UV detection. After complete conversion, water was added and the product was extracted with DCM which was purified by column chromatography to get the desired quinolone adduct.

Reference： [1]Venepally, Vijayendar; Prasad; Poornachandra; Kumar, C. Ganesh; Jala, Ram Chandra Reddy [Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 2, p. 613 - 617]

61
[ 38460-95-6 ]
[ 29601-98-7 ]
N-benzyl-N-hydroxyundec-10-enamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;
98%	With triethylamine In dichloromethane at 0 - 20℃; for 10h; Inert atmosphere;	[General procedure F]N-Benzyl-N-hydroxyoctanamide (4a) General procedure: Triethylamine (2.0 mL, 14.3 mmol, 2.0 equiv) was added to a solution of N-benzyl-N-hydroxyamine hydrochloride 46 (1.13 g, 7.10 mmol, 1.0 equiv) and CH2Cl2 (47 mL) at 0 °C. After maintaining for 10 min at 0 °C, a solution of octanoylchloride (1.2 mL, 7.1 mmol, 1.0 equiv) and CH2Cl2 (35 mL) was added to this solution at 0 °C. The resulting solution was allowed to warm to room temperature, maintained for 10 h at room temperature, and quenched with saturated aqueous NaHCO3 (80 mL). This mixture was extracted with CH2Cl2 (2x 20 mL). The combined organic extracts weredried over Na2SO4, and concentrated. The residue was purified by silica gel column chromatography (EtOAc/hexane1:4 to 1:2) to give 1.66 g of N-hydroxyamide 4a (94%):

Reference： [1]Katahara, Seiya; Kobayashi, Shoichiro; Fujita, Kanami; Matsumoto, Tsutomu; Sato, Takaaki; Chida, Noritaka [Journal of the American Chemical Society, 2016, vol. 138, # 16, p. 5246 - 5249]
[2]Katahara, Seiya; Kobayashi, Shoichiro; Fujita, Kanami; Matsumoto, Tsutomu; Sato, Takaaki; Chida, Noritaka [Bulletin of the Chemical Society of Japan, 2017, vol. 90, # 8, p. 893 - 904]

62
[ 38460-95-6 ]
[ 1468-95-7 ]
anthracen-9-ylmethyl undec-10-enoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	With pyridine at 20℃; Cooling with ice; Inert atmosphere;	4.2. Anthracen-9-ylmethyl-undec-10-enoate (3) A solution of 32.3 g 9-anthracene methanol (0.155 mmol,1 equiv) in dry pyridine (300 mL) under inert atmosphere was cooled in an ice bath, while adding 50 mL of distilled undecenoyl chloride (0.23 mmol,1.5 equiv). After a night of stirring at room temperature, the reaction mixture was washed with water (100 mL) and brine (100 mL). The combined aqueous phases were extracted with diethyl ether (350 mL). The combined organic phases were dried over magnesium sulfate and concentrated in vacuo. Chromatography over silica, eluting with a gradient from heptane to chloroform, resulted in anthracen-9-yl methyl-undec-10-enoate 3 as a yellow solid (41.9 g, 71%); Mp=49-50.5 °C; Rf (25% CHCl3/hexane) 0.42; 1H NMR (400 MHz, CDCl3): δ (ppm)1.15-1.40 (m, 10H, CH2CH2CH2), 1.62 (quin, J=7.2 Hz, 2H, COCH2CH2), 2.02 (q, J=7.3 Hz, 2H, CH2CHCH2), 2.34 (t, J=7.5 Hz, 2H, COCH2CH2), 4.90-5.03 (m, 2H, CH2CHCH2), 5.73-5.88 (m, 1H, CH2CHCH2), 6.17 (s, 2H, CCH2O), 7.47-7.54 (m, 2H, CH2CCCHCHCH), 7.56-7.61 (m, 2H, CH2CCCHCHCH), 8.05 (d, J=8.4 Hz, 2H, CHCCHCH), 8.35 (dd, J=8.9 Hz, J=0.8 Hz, 2H, CCCHCH), 8.52 (s, 1H, CCHC); 13C NMR (100 MHz, CDCl3): δ (ppm) 25.0 (CH2), 28.9 (CH2), 29.0 (CH2), 29.1 (CH2), 29.2 (CH2), 29.3 (CH2), 33.8 (CH2), 34.3 (CH2), 58.7 (CH2), 114.1 (CH2), 124.0 (CH), 125.1 (CH), 126.4 (C), 126.6 (CH), 129.1 (CH), 131.1 (C), 131.4 (C), 139.2 (CH), 174.2 (C); IR vmax cm-1: 2922, 2848, 1726, 1386, 1318, 1278, 1244, 1210, 1158, 1060; LC-MS (m/z) 191.1 [C15H11]+; GC-MS (m/z) 191.1 [C15H11]+, 374.2 [M]; HRMS (m/z for [MH]): calcd: 375.232; found: 375.231; only traces of the molecular ion were found in LC-MS and HRMS, probably due to very efficient fragmentation forming [C15H11]+. In GC-MS both the molecular ion and fragment product were found (Supplementary data, Figs. S11 and S12).

Reference： [1]Van Damme, Jonas; Vlaminck, Laetitia; Van Assche, Guy; Van Mele, Bruno; van den Berg, Otto; Du Prez, Filip [Tetrahedron, 2016, vol. 72, # 29, p. 4303 - 4311]

63
[ 38460-95-6 ]
[ 827-43-0 ]
1-(4-methyl-2-phenyl-1H-imidazol-1-yl)undec-10-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; for 3h;Reflux;	10-undecenoic acid chloride(2.5 g, 0.012 mol) was dissolved in THF (20 mL), was prepared monocarboxylic acid chloridesolution.On the other hand, <strong>[827-43-0]4-methyl-2-phenylimidazole</strong> (4 g, 0.025 mol) and dissolved in THF (40 mL),was prepared amine solution.Then, the amine solution was added to the monocarboxylic acid chloride solution to obtain areaction liquid.After the reaction solution was refluxed for 3 h on a water bath under reduced pressure, THF inthe reaction solution was distilled off.Then, water and ethyl acetate to the reaction solution was added to distribution, it was toseparate the ethyl acetate layer was separated. After the ethyl acetate layer was once washedwith water, by distilling off the ethyl acetate, to give the crude product.The crude product was purified by silica gel column chromatography and purified by (eluentethyl acetate) to give 1- (4-methyl-2-phenyl -1H- imidazol-1-yl) Undekku -10-en-1-one ( thechemical formula corresponds to (6)) (C 21 H 28 N 2 O), was obtained as a brown oil.
	In tetrahydrofuran; for 3h;Reflux;	10-undecenoyl chloride (2.5 g, 0.012 mol) was dissolved in THF (20 mL) to prepare a monocarboxylic acid chloride solution.On the other hand, <strong>[827-43-0]4-methyl-2-phenylimidazole</strong> (4 g, 0.025 mol) was dissolved in THF (40 mL) to prepare an amine solution.Then, the amine solution was added to the monocarboxylic acid chloride solution to prepare a reaction solution.After the reaction solution was refluxed on a water bath for 3 hours, THF in the reaction liquid was distilled off under reduced pressure.Then, water and ethyl acetate were added to the reaction solution and partitioned, and the ethyl acetate layer was separated. The ethyl acetate layer was once washed with water and then ethyl acetate was distilled off to obtain a crude product.The crude product was purified by silica gel column chromatography (developing solvent: ethyl acetate)1- (4-methyl-2-phenyl-1H-imidazol-1-yl) undec-10-en-1-one (corresponding to the above chemical formula (6)) (C21 H28 N2 O) was obtained as a brown oil.

Reference： [1]Patent: JP5836086,2015,B2 .Location in patent: Paragraph 0179-0183
[2]Patent: JP2015/172082,2015,A .Location in patent: Paragraph 0178-0183

64
[ 98-50-0 ]
[ 38460-95-6 ]
[ 860526-77-8 ]

Yield	Reaction Conditions	Operation in experiment
87%	In ethanol for 4h; Cooling with ice;	16 when p-arsanilic acid (about 14.28 g, about 65.8 mmol) was dissolved in absolute ethanol (about 150 mL) and was chilled in an ice- water bath with stirring. 10-Undecenoyl chloride (about 17 mL, about 16 g, about 79 mmol) was added dropwise. The mixture was stirred for approximately 4 hours, and water was added to precipitate out the product, which was then filtered by suction and dried overnight. Analysis of the product of the reaction shows the yield of desired compound to be about 87%.

Reference： [1]Current Patent Assignee: MERCK KGAA - TW2016/2081, 2016, A Location in patent: Page/Page column 38

65
[ 38460-95-6 ]
methyl 1-(3-phenylpropyl)-1H-pyrrole-2-carboxylate [ No CAS ]
methyl 1-(3-phenylpropyl)-4-undec-10-enoyl-1H-pyrrole-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With ytterbium(III) triflate In nitromethane at 0 - 20℃; for 18h;
42%	With ytterbium(III) triflate In nitromethane at 0 - 20℃; for 18h;	1.2 Step 2: Preparation of methyl 1- (3-phenylpropyl) -4-undec-10-enoyl-1H-pyrrole-2-carboxylate (Compound 7a) 10-undecenoyl chloride (728 mg, 2.12 mmol) and Ytterbium (III) trifluoromethanesulfonate (101.6 mg, 0.164 mmol) was added to a solution of Compound 6 (400 mg, 1.64 mmol) obtained in the above step 1 was slowly added to the nitromethane solution contained at 0 . The reaction mixture was stirred at room temperature for 18 hours. The reaction was terminated by addition of NaHCO3 (15 mL) and the mixture was extracted with diethyl ether (3 x 15 mL). The organic layer was washed with water and brine, dried over Na2SO4, and the volatiles were removed in vacuo. The reaction residue was purified by silica gel column chromatography (Hexane-Ethyl acetate, 20: 1) to give compound 7a as a colorless oil (281 mg, 42%).

Reference： [1]Gunasekaran, Pethaiah; Lee, So-Rim; Jeong, Seung-Min; Kwon, Jeong-Woo; Takei, Toshiki; Asahina, Yuya; Bang, Geul; Kim, Seongnyeon; Ahn, Mija; Ryu, Eun Kyung; Kim, Hak Nam; Nam, Ki-Yub; Shin, Song Yub; Hojo, Hironobu; Namgoong, Suk; Kim, Nam-Hyung; Bang, Jeong Kyu [ChemMedChem, 2017, vol. 12, # 8, p. 580 - 589]
[2]Current Patent Assignee: CHUNGBUK NATIONAL UNIVERSITY - KR101879983, 2018, B1 Location in patent: Paragraph 0106-0107; 0113-0114

66
[ 38460-95-6 ]
[ 39987-25-2 ]
10-amidoundec-1-eneiminodiacetic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With pyridine; In diethyl ether; for 2h;Reflux;	Step 1: Synthesis of 10-amidoundec-1-eneiminodiacetic acid methyl ester Added to a solution of dimethyliminodiacetate (hydrochloride) (3.08 g; 16 mmol) dissolved in 50 ml of anhydrous ether was pyridine (2.46 g; 2.59 ml; 35 mmol; 2 eq.). The solution was heated under reflux of ether and the undecenoyl chloride (97%) (3.48 g, 3.7 ml, 17 mmol, 1 eq.) was added very slowly (approximately over a period of one hour). The reaction was continued under reflux of ether for 1 hour. The reaction mixture was filtered, then the filtrate was concentrated to give a residue which was then purified by chromatography over silica gel (cyclohexane?cyclohexane/ethyl acetate (70/30)) to give a white solid. The characteristics of the product obtained were the following: Mass obtained: 3.85 g Yield: 74% 1H NMR (200 MHz; CDCl3): 1.30 (10H; m; H7-11); 1.64 (2H; m; H6); 2.03 (2H; m; H12); 2.30 (2H; t; H5; JH-H=7.4 Hz); 3.72 (3H; s; H1); 3.77 (3H; s; H1); 4.16 (2H; s; H3); 4.19 (2H; s; H3); 4.96 (2H; m; H14); 5.81 (1H; m; H13) 13C NMR (200 MHz; CDCl3): 25.18 (C6); 29.28; 29.45; 29.59; 29.69; 29.74; 33.06 (C5); 34.18 (C12); 48.18 (C3); 50.34 (C3); 52.53 (C1); 52.90 (C1); 114.52 (C14); 139.58 (C13); 169.88 (C2); 170.30 (C2); 174.02 (C4)

Reference： [1]Patent: US9657042,2017,B2 .Location in patent: Page/Page column 24; 25

67
[ 38460-95-6 ]
[ 39987-25-2 ]
1-trimethoxysilanyl-10-amidoundecyl-11-iminodiacetic acid methyl ester [ No CAS ]

Reference： [1]Patent: US9657042,2017,B2

68
[ 38460-95-6 ]
[ 771-61-9 ]
pentafluorophenyl ω-undecenoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With pyridine In diethyl ether for 2h; Reflux;	5.a.1 Synthesis ofpentafluorophenylundec- 1 -ene ester Added to a solution of pentafluorophenol (6.51 g; 35mmol, 1 eq.) dissolved in 60 ml of anhydrous ether waspyridine (2.8 g; 2.9 ml; 35 mmol; 1 eq.). The solution washeated under reflux of ether and undecenoyl chloride (97%)(7.4 g; 7.8 ml; 35 mmol; 1 eq.) was added very slowly (overa period of around 1 hour). The reaction was continuedunder reflux of ether for 1 hour. The reaction mixture wasfiltered, then the filtrate was concentrated to give a colourless liquid.The characteristics of the product obtained were thefollowing:Mass obtained: 12.36 gYield: 100%‘H NMR (200 MHz; CDC13): 1.37 (1OH; m; H’°-’j; 1.80(2H; m; H9); 2.09 (2H; m; H’5); 2.70 (2H; t; H8 3HH=Hz) 5.01 (2H; m; H’7); 5.85 (1H; m; H’6)‘3C NMR (200 MHz; CDC13): 25.16; 29.23; 29.28; 29.42;29.49; 29.63; 33.72; 34.18; 114.55 (C’7); 135.78-140.77(2C; m; C35 ‘Jc+F=251 Hz); 137.29-142.3 1 (2C; m; C26‘Jc_,=253 Hz); 138.99 (C4); 139.51 (C’6); 144.07 (C’);169.97 (C7)F NMR (400 MHz; CDC13): -153.38 (2F; d; F34 3JFF=17.1 Hz); -158.82 (t; F’; 3JFF=21.6 Hz; -163.02 (2F; t; F25 3JF_F=16.8 Hz)
73.5%	With pyridine In diethyl ether for 1h; Reflux;

Reference： [1]Current Patent Assignee: COMMISSARIAT A L'ENERGIE ATOMIQUE ET AUX ENERGIES ALTERNATIVES - US9657042, 2017, B2 Location in patent: Page/Page column 22
[2]Liu; Yang; Traulsen; Cornelissen [Chemical Communications, 2017, vol. 53, # 54, p. 7632 - 7634]

69
[ 38460-95-6 ]
[ 928-96-1 ]
(Z)-hex-3-en-1-yl undec-10-enoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With pyridine In dichloromethane at 0 - 20℃; for 4h;
95%	With pyridine In dichloromethane at 0 - 20℃; for 4h;	3 Example 3Synthesis of (Z)-hex-3-en-1-yl undec-lO-enoate (8) To a 100 mL round-bottom flask charged with a stir bar were added dichloromethane (20 mL), undecenoyl chloride (2.37 mL, 11.0 mmol), and pyridine (0.89 mL, 11.0 mmcl). Cis-3-hexenol (1.18 mL, 10.0 mmol) was then added dropwise at 0 °C. The reactionmixture was brought to room temperature and stirred for 4 h. The reaction mixture was extracted with IM aq. HCI (200 mL) and sat. aq. NaHCO3 (200 mL). The organic layer was dried over anhydrous MgSO4, filtered, and the solvents were removed under vacuum. The product was purified by column chromatography on silica gel (5:95 Et20:pentane) to yield a colorless oil (2.53 g, 95% yield).1H NMR (400 MHz, CDCI3) ö 5.80 (ddt, J = 16.9, 10.2, 6.7 Hz, IH), 5.55-5.45 (m, IH),5.36-5.26 (m, 1H), 4.99 (dq, J= 17.1, 1.7 Hz, 1H), 4.92 (ddt, J= 10.2, 2.3, 1.2 Hz, 1H),4.06 (t, J = 6.9 Hz, 2H), 2.43 - 2.31 (m, 2H), 2.32 -2.24 (m, 2H), 2.04 (dddd, J = 14.8,7.9, 5.0, 1.5 Hz, 4H), 1.67 - 1.54 (m, 2H), 1.42 - 1.33 (m, 2H), 1.33 - 1.24 (m, 8H), 0.97(t, J = 7.5 Hz, 3H).‘3C NMR (101 MHz, CDCI3) 6 174.06, 139.32, 134.63, 123.92, 114.28, 63.89, 34.49,33.94, 29.43, 29.35, 29.26, 29.20, 29.04, 26.90, 25.11, 20.75, 14.39. HRMS (FAB+): [M] C17H3002 Calculated - 266.2246, Found - 266.2216.
95%	With pyridine In dichloromethane at 0 - 20℃;	4 Example 4. Synthesis of (Z)-3-Hexenyl 10-undecenoate To a 100 mL round-bottom flask charged with a stir bar were added 20 ml dichloromethane, undecenoyl chloride (2.37 mL, 1 1.0 mmol), and pyridine (0.89 mL, 1 1.0 mmol). C/.v-3-hcxcnol (1.18 mL, 10.0 mmol) was then added dropwise at 0 °C. The reaction mixture was brought to room temperature and stirred for 4 h. The reaction mixture was extracted with 1M aq. HC1 (200 mL) and sat. aq. NaHCCh (200 mL). The organic layer was dried over anhydrous MgSCL, filtered, and solvents were removed in vacuum. The product was purified by column chromatography on silica gel (5:95 Et20: pentane) to yield a colorless oil (2.53 g, 95% yield). The 'H NMR and 13C NMR data correspond to the data found in the literature.

Reference： [1]Ahmed, Tonia S.; Grubbs, Robert H. [Angewandte Chemie - International Edition, 2017, vol. 56, # 37, p. 11213 - 11216][Angew. Chem., 2017, vol. 129, p. 11365 - 11368,4]
[2]Current Patent Assignee: CALIFORNIA INSTITUTE OF TECHNOLOGY - WO2018/208501, 2018, A1 Location in patent: Page/Page column 44
[3]Current Patent Assignee: UMICORE - WO2019/158485, 2019, A1 Location in patent: Paragraph 000153

70
[ 38460-95-6 ]
[ 64275-73-6 ]
(Z)-oct-5-en-1-yl undec-10-enoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With pyridine In dichloromethane at 0 - 20℃; for 4h;
96%	With pyridine In dichloromethane at 0 - 20℃; for 4h;	6 Example 6Synthesis of (Z)-oct-5-en-1 -yl undec-1 0-enoate (11) To a 100 mL round-bottom flask charged with a stir bar were added dichloromethane (20 mL), undecenoyl chloride (2.37 mL, 11.0 mmcl), and pyridine (0.89 mL, 11.0 mmcl). Cis-5-octenol (1.51 mL, 10.0 mmcl) was added dropwise at 0 °C; the reaction mixture was brought to room temperature and stirred for 4 h. The reaction mixture was extractedwith 1M aq. HCI (200 mL) and sat. aq. NaHCO3 (200 mL). The organic layer was driedover anhydrous MgSO4, filtered, and the solvents were removed under vacuum. Theproduct was purified by column chromatography on silica gel (5:95 Et20: pentane) to yielda colorless oil (2.82 g, 96% yield).1H NMR (400 MHz, CDCI3) ö 5.82 (ddt, J = 16.9, 10.1, 6.7 Hz, IH), 5.46-5.37 (m, IH),5.36 - 5.25 (m, 1 H), 5.01 (dq, J = 17.1 1.8 Hz, 1 H), 4.94 (ddt, J = 10.2, 2.4, 1.2 Hz, 1 H),4.08 (t, J = 6.7 Hz, 2H), 2.31 (t, J = 7.6 Hz, 2H), 2.06 (dddd, J = 10.9, 9.5, 5.3, 1.6 Hz,6H), 1.72-1.61 (m, 4H), 1.47-1.27 (m, 12H), 0.97 (t, J= 7.5 Hz, 3H).13 NMR (101 MHz, CDCI3) O 173.99, 139.17, 132.16, 128.49, 114.14, 64.22, 34.39,33.80, 29.31, 29.22, 29.14, 29.07, 28.90, 28.23, 26.63, 26.05, 25.02, 20.54, 14.36. HRMS (FAB+): [M+H] C19H3502 Calculated - 295.2637, Found - 295.2639.
96%	With pyridine In dichloromethane at 0 - 20℃;	7 Example 7. Synthesis of (Z)-5-Octenyl 10-undecenoate To a 100 mL round-bottom flask charged with a stir bar were added 20 ml . dichloromethane, undecenoyl chloride (2.37 mL, 11.0 mmol), and pyridine (0.89 mL, 1 1.0 mmol). C/.v-5-octcnol (1.51 mL, 10.0 mmol) was then added dropwise at 0 °C; the reaction mixture was brought to room temperature and stirred for 4 h. The reaction mixture was extracted with 1M aq. HC1 (200 mL) and sat. aq. NaHCCh (200 mL). The organic layer was dried over anhydrous MgS04, filtered, and solvents were removed in vacuum. The product was purified by column chromatography on silica gel (5:95 Et20: pentane) to yield a colorless oil (2.82 g, 96% yield). The 'H NMR and 13C NMR data correspond to the data found in the literature.

Reference： [1]Ahmed, Tonia S.; Grubbs, Robert H. [Angewandte Chemie - International Edition, 2017, vol. 56, # 37, p. 11213 - 11216][Angew. Chem., 2017, vol. 129, p. 11365 - 11368,4]
[2]Current Patent Assignee: CALIFORNIA INSTITUTE OF TECHNOLOGY - WO2018/208501, 2018, A1 Location in patent: Page/Page column 46; 47
[3]Current Patent Assignee: UMICORE - WO2019/158485, 2019, A1 Location in patent: Paragraph 000156

71
[ 38460-95-6 ]
(Z)-6-nonenol [ No CAS ]
(Z)-non-6-en-1-yl undec-10-enoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With pyridine In dichloromethane at 0 - 20℃; for 4h;
89%	With pyridine In dichloromethane at 0 - 20℃; for 4h;	7 Example 7Synthesis (Z)-non-6-en-1-yl undec-lO-enoate (12) To a 100 mL round-bottom flask charged with a stir bar were added dichloromethane (20 mL), undecenoyl chloride (2.37 mL, 11.0 mmcl), and pyridine (0.89 mL, 11.0 mmcl). Cis-6-nonenol (1.67 mL, 10.0 mmcl) was then added dropwise at 0 °C. The reaction mixture was brought to room temperature and stirred for 4 h. The reaction mixture wasextracted with IM aq. HCI (200 mL) and sat. aq. NaHCO3 (200 mL). The organic layer was dried over anhydrous MgSO4, filtered, and the solvents were removed under vacuum. The product was purified by column chromatography on silica gel (5:95 Et20:pentane) to yield a colorless oil (2.74 g, 89% yield).1H NMR (400 MHz, CDCI3) O 5.80 (ddt, J = 16.9, 10.2, 6.7 Hz, 1H), 5.50-5.16 (m, 2H),5.04 - 4.94 (m, I H), 4.94 - 4.88 (m, I H), 4.05 (t, J = 6.7 Hz, 2H), 2.35 - 2.22 (m, 2H),2.13-1.96 (m, 6H), 1.61 (dt, J= 11.8, 4.1 Hz, 4H), 1.36 (dt, J= 6.5, 2.2 Hz, 6H), 1.32-1.25 (m, 8H), 0.95 (t, J = 7.5 Hz, 3H).‘3C NMR (101 MHz, CDCI3) 6 174.14, 139.32, 131.99, 128.96, 114.28, 64.47, 34.54,33.94, 29.48,29.44,29.36,29.28,29.21,29.03,28.70,27.07,25.70,25.15, 20.66, 14.52.HRMS (FAB+): [M] C20H3702 Calculated - 309.2794, Found - 309.2779.
89%	With pyridine In dichloromethane at 0 - 20℃;	8 Example 8. Synthesis (Z)-6-Nonenyl 10-undecenoate To a 100 mL round-bottom flask charged with a stir bar were added 20 ml . dichloromethane, undecenoyl chloride (2.37 mL, 1 1.0 mmol), and pyridine (0.89 mL, 1 1.0 mmol). C/.v-6-noncnol (1.67 mL, 10.0 mmol) was then added dropwise at 0 °C. The reaction mixture was brought to room temperature and stirred for 4 h. The reaction mixture was extracted with 1M aq. HC1 (200 mL) and sat. aq. NaHCCh (200 mL). The organic layer was dried over anhydrous MgSCL, filtered, and solvents were removed in vacuum. The product was purified by column chromatography on silica gel (5:95 Et20: pentane) to yield a colorless oil (2.74 g, 89% yield). The 'H NMR and 13C NMR data correspond to the data found in the literature.

Reference： [1]Ahmed, Tonia S.; Grubbs, Robert H. [Angewandte Chemie - International Edition, 2017, vol. 56, # 37, p. 11213 - 11216][Angew. Chem., 2017, vol. 129, p. 11365 - 11368,4]
[2]Current Patent Assignee: CALIFORNIA INSTITUTE OF TECHNOLOGY - WO2018/208501, 2018, A1 Location in patent: Page/Page column 47
[3]Current Patent Assignee: UMICORE - WO2019/158485, 2019, A1 Location in patent: Paragraph 000157

72
[ 38460-95-6 ]
[ 928-91-6 ]
(Z)-hex-4-en-1-yl undec-10-enoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With pyridine In dichloromethane at 0 - 20℃; for 4h;
92%	With pyridine In dichloromethane at 0 - 20℃; for 4h;	5 Example 5Synthesis of (Z)-hex-4-en-1 -yl undec-1 0-enoate (10) To a 100 mL round-bottom flask charged with a stir bar were added dichloromethane (20 mL), undecenoyl chloride (2.37 mL, 11.0 mmol), and pyridine (0.89 mL, 11.0 mmol). Cis-4-hexenol (1.17 mL, 10.0 mmol) was added dropwise atO °C. The reaction mixture was brought to room temperature and stirred for 4 h. The reaction mixture was extracted with 1M aq. HCI (200 mL) and sat. aq. NaHCO3 (200 mL). The organic layer was dried over anhydrous MgSO4, filtered, and the solvents were removed under vacuum. Theproduct was purified by column chromatography on silica gel (5:95 Et20: pentane) to yielda colorless oil (2.45 g, 92% yield).1H NMR (400 MHz, CDCI3) 65.80 (ddt, J = 16.9, 10.2, 6.7 Hz, IH), 5.49 (dddd, J = 10.7,8.2, 6.7, 5.2 Hz, 1 H), 5.36 (dtq, J = 10.7, 7.3, 1.7 Hz, 1 H), 4.99 (dq, J = 17.2, 1.8 Hz, 1 H),4.92 (ddt, J = 10.2, 2.3, 1.2 Hz, I H), 4.06 (t, J = 6.6 Hz, 2H), 2.29 (t, J = 7.5 Hz, 2H), 2.11(qt, J = 7.2, 1.2 Hz, 2H), 2.07 - 1.99 (m, 2H), 1.73 - 1.64 (m, 2H), 1.60 (ddt, J = 6.7, 1.8,0.9 Hz, 6H), 1.36 (dt, J = 8.3, 4.8 Hz, 2H), 1.28 (q, J = 4.1 3.3 Hz, 7H).‘3C NMR (101 MHz, CDCI3) 6 174.12, 139.33, 129.26, 125.04, 114.28, 63.89, 34.54,33.94, 29.44, 29.36, 29.28, 29.21, 29.04, 28.58, 25.15, 23.33, 12.86.HRMS (FAB÷): [Mi-H] C17H3102 Calculated - 267.2324, Found - 267.2335.
92%	With pyridine In dichloromethane at 0 - 20℃;	6 Example 6. Synthesis of (Z)-4-Hexenyl 10-undecenoate To a 100 mL round-bottom flask charged with a stir bar were added 20 ml dichloromethane, undecenoyl chloride (2.37 mL, 1 1.0 mmol), and pyridine (0.89 mL, 1 1.0 mmol). C/.v-4-hcxcnol (1.17 mL, 10.0 mmol) was then added dropwise at 0 °C. The reaction mixture was brought to room temperature and stirred for 4 h. The reaction mixture was extracted with 1M aq. HC1 (200 mL) and sat. aq. NaHCCh (200 mL). The organic layer was dried over anhydrous MgSCL, filtered, and solvents were removed in vacuum. The product was purified by column chromatography on silica gel (5:95 Et20: pentane) to yield a colorless oil (2.45 g, 92% yield). The 'H NMR and 13C NMR data correspond to the data found in the literature.

Reference： [1]Ahmed, Tonia S.; Grubbs, Robert H. [Angewandte Chemie - International Edition, 2017, vol. 56, # 37, p. 11213 - 11216][Angew. Chem., 2017, vol. 129, p. 11365 - 11368,4]
[2]Current Patent Assignee: CALIFORNIA INSTITUTE OF TECHNOLOGY - WO2018/208501, 2018, A1 Location in patent: Page/Page column 45; 46
[3]Current Patent Assignee: UMICORE - WO2019/158485, 2019, A1 Location in patent: Paragraph 000155

73
[ 38460-95-6 ]
[ 107-97-1 ]
N-undecylenoyl sarcosine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With sodium hydroxide In water at 20 - 35℃; for 4h;	1 E xample 1 : Preparation of N-undecylenoyl sarcosine To a stirred mixture of sarcosine (291 g of 40 % aqueous solution, 1.05 gmol) in water (390g) at 25 eC, undecylenoyi chloride (207g, 1.0 gmol) and sodium hydroxide solution (83g of 48% aqueous solution, 1gmol) are added simultaneously while maintaining temperature between 20 eC to 30 eC and pH between 10.0 to 11.0. The addition takes about two hours. The reaction mass is stirred for additional two hours at 30 eC to 35 eC. The whole reaction mixture is then acidified with sulphuric acid and the aqueous phase containing the inorganic salt is separated from the organic phase. The organic phase is washed again with water to ensure that the organic phase is free from mineral acidity. The isolated organic phase contains N-undecylenoyl sarcosine as colorless liquid (240g, 94% yield). (0081) Analysis of N-undecylenoyl sarcosine: (0082) Acid val ue = 215, M oisture content = < 1 % (0083) IR (neat cm 1): 1603, 1732, 2854, 2925 (0084) 1H-NM R (CDCI3): 1.21-1.29 (10 H), 1.32-1.56 (2H), 1.93-1.98 (2H), 2.30- 2.33(2H), 2.9-3.1(31-1, two singlets, N-methyl), 3.9-4.0 (2H, methylene of sarcosine, two singlets), 4.83-4.93 (2H), 5.67-5.78(1 H), 9.0 (1 H, carboxyl)

Reference： [1]Current Patent Assignee: GALAXY SURFACTANTS LTD. - WO2017/141266, 2017, A1 Location in patent: Page/Page column 14-15

74
[ 38460-95-6 ]
[ 2177-63-1 ]
C₂₂H₃₁NO₅ [ No CAS ]

Reference： [1]RSC Advances,2017,vol. 7,p. 47507 - 47519

75
[ 38460-95-6 ]
[ 2177-63-1 ]
C₃₃H₅₂N₂O₄ [ No CAS ]

Reference： [1]RSC Advances,2017,vol. 7,p. 47507 - 47519

76
[ 38460-95-6 ]
[ 652-67-5 ]
[ 835595-24-9 ]

Yield	Reaction Conditions	Operation in experiment
86%	With triethylamine In acetone at 20℃; for 26h; Cooling with ice;	5 Respectively, taking isosorbide 1.0g,4.2 g of undecenoyl chloride and 10 g of acetone in a 100 mL flask,Under ice-cooling, 2.1 g of triethylamine was added dropwise to the flask with a constant pressure dropping funnel.The reaction was allowed to react for 2 hours in an ice bath and then warmed to room temperature for 24 h. The reaction was carried out by filtration, and the acetone solvent was removed by steaming and the residue was extracted with ethyl acetate.And then washed with 1% aqueous sodium hydroxide solution and distilled water, dried over anhydrous magnesium sulfate, and then filtered and steamed to obtain isosorbide-based active monomer. (Yield: 86%)

Reference： [1]Current Patent Assignee: JIANGXI SCIENCE & TECHNOLOGY NORMAL UNIVERSITY - CN105001088, 2017, B Location in patent: Paragraph 0009; 0034; 0035

77
[ 38460-95-6 ]
[ 824-46-4 ]
C₂₉H₄₄O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In ethyl acetate at 20℃; for 26h; Cooling with ice;	1.2 2 g of vanilly aldehyde diol,Triethylamine 4.3 g and ethyl acetate 10 g in a 100 mL flask,In the ice bath,8.6 g of undecenoyl chloride was added dropwise to the flask with a constant pressure dropping funnel.The reaction was first reacted in an ice bath for 2 h,And then heated to room temperature for 24 h,The liquid phase was washed with 1% aqueous sodium hydroxide solution and distilled water, dried over anhydrous magnesium sulfate, and then filtered and steamed to obtain vanillin-based active monomer. (Two-step total yield: 82%).

Reference： [1]Current Patent Assignee: JIANGXI SCIENCE & TECHNOLOGY NORMAL UNIVERSITY - CN105001088, 2017, B Location in patent: Paragraph 0009; 0017; 0019

78
[ 38460-95-6 ]
[ 149-91-7 ]
C₄₀H₆₀O₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With triethylamine In acetone at 20℃; for 26h; Cooling with ice;	3 Gallic acid 1. g were taken, Undecenoyl chloride 5.4 g and acetone lOg In a 100 mL flask, 2.7 g of triethylamine was added dropwise to the flask with a constant pressure dropping funnel under ice-cooling.Reaction in the ice bath first reaction 2h, and then heated to room temperature reaction 24h,Filtration, spin steam to remove acetone solvent, use ethyl acetate as solvent.And then washed with 1% aqueous sodium hydroxide solution and distilled water respectively, dried over anhydrous magnesium sulfate, and then filtered and steamed to obtain a gallic acid-based active monomer. (Yield: 78%)

Reference： [1]Current Patent Assignee: JIANGXI SCIENCE & TECHNOLOGY NORMAL UNIVERSITY - CN105001088, 2017, B Location in patent: Paragraph 0010; 0022; 0023

79
[ 38460-95-6 ]
C₂₉H₅₈N₂O₂P₂ [ No CAS ]
C₅₁H₉₄N₂O₄P₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With magnesium chloride In acetonitrile at 25 - 65℃; for 5h;	5 Example 5 In a 3000 mL four-necked flask equipped with a reflux condenser, a thermometer, a stirrer, and a constant pressure dropping funnel, 236.8 g of Mannich base, 9.8 g of anhydrous magnesium chloride and 800 mL of acetonitrile were charged and sufficiently dissolved under stirring.162.2g undecenoyl chloride was added into a four-necked flask under stirring at 25 ° C. After the addition of undecenoyl chloride was completed, the temperature was raised to 65 ° C and reacted at this temperature for 6 hours. After the reaction was completed, The solvent was distilled off and the residual solid was washed three times with deionized water to give a white solid, which was vacuum dried for 6 hours at 50 ° C to give 321.6 g of product in 87.0% yield.

Reference： [1]Current Patent Assignee: CHINA PETROCHEMICAL CORPORATION - CN104610351, 2017, B Location in patent: Paragraph 0061; 0062; 0063; 0064

80
[ 38460-95-6 ]
C₃₄H₇₀N₂O₂P₂ [ No CAS ]
C₅₆H₁₀₆N₂O₄P₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87.5%	With magnesium chloride In acetonitrile at 25 - 65℃; for 6.5h;	5 Example 5 In a 3000 mL four-necked flask equipped with a reflux condenser, a thermometer, a stirrer, and a constant-pressure dropping funnel, 265.6 g of Mannich's base, 9.8 g of anhydrous magnesium chloride and 800 mL of acetonitrile were charged and sufficiently dissolved under stirring.162.2g undecenoyl chloride was added to a four-necked flask under stirring at 25 ° C. After the addition of undecenoyl chloride was completed, the temperature was raised to 65 ° C and reacted at this temperature for 6.5 hours. After the reaction was completed, The solvent was distilled off under pressure and ether was added to dissolve the residue. The ether layer was washed with deionized water three times and the ether was distilled off to obtain 348.6 g of a light yellow liquid product in a yield of 87.5%.The structure of the product was confirmed by FTIR and NMR test.Indoor loop test analysis shows that the product is configured as an ethanol solution, atomized into the loop, the test pressure 0.5-0.6MPa, when the drag reducing agent concentration of 10g / L, the average drag reduction rate can reach 10.0%, the expiration date More than 60 days.

Reference： [1]Current Patent Assignee: CHINA PETROCHEMICAL CORPORATION - CN104610350, 2017, B Location in patent: Paragraph 0060; 0061; 0062; 0063

81
[ 38460-95-6 ]
Ν,Ο-dimethylhydroxylamine hydrochloride [ No CAS ]
[ 102613-04-7 ]

Yield	Reaction Conditions	Operation in experiment
96.8%	In dichloromethane at 5 - 10℃;	2.1 Step one amidation At room temperature, 344 ml of methylene chloride and 34.4 g of N,O-dimethylhydroxylamine hydrochloride were added to the reaction vessel at a time, the temperature was lowered to 5°C, a solution of molecular A in dichloromethane was added dropwise, and the reaction was warmed up to 10°C. ;The reaction was detected by GC. After the reaction was completed, 400 ml of 5 wt% dilute hydrochloric acid was added dropwise to the reaction vessel. The mixture was stirred well for 20 to 60 minutes, and the liquid was separated. The aqueous phase was extracted three times with 300 ml of dichloromethane, and the dichloromethane phases were combined, dried and concentrated. Obtained 62.0g B, gas chromatography mass spectrometry purity 96.3%, yield 96.8%;

Reference： [1]Current Patent Assignee: SHIJIAZHUANG HEZHONG TECH - CN106117026, 2016, A Location in patent: Paragraph 0014; 0015; 0016; 0017

82
[ 38460-95-6 ]
[ 5470-95-1 ]
2,3-dimethoxybenzaldehyde O-undec-10-enoyl oxime [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;

Reference： [1]Vijayendar, Venepally; Kaki, Shiva Shanker; Vamshi Krishna; Misra, Sunil; Prasad; Jala, Ram Chandra Reddy [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2018, p. 1015 - 1022]

83
[ 38460-95-6 ]
[ 928-97-2 ]
(E)-hex-3-en-1-yl undec-10-enoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With pyridine In dichloromethane at 0 - 20℃; for 4h;	1 Example 1 Synthesis of (E)-hex-3-en-1-yl undec-10-enoate [198] To a round-bottom flask charged with a stir bar were added 20 mL dieh.oromethane, undecenoyl chloride (2.37 mL, 1 1.0 mmol), and pyridine (0.89 mL, 1 1.0 mmol). 7rans-3-hexen-l-ol (1.22 mL, 10.0 mmol) w'as then added dropwise at 0 °C. The reaction mixture was brought to room temperature and stirred for 4 h. The reaction mixture was extracted with 1M aq. HC1 (200 mL) and saturated aq. NaHC( (200 mL). The organic layer was dried over anhydrous MgS04, filtered, and solvents were removed in vacuo. The product w'as purified by column chromatography on silica gel (5:95 Et20: pentane) to yield a colorless oil (2.53 g, 95% yield). NMR (400 MHz, Chloroform-rfi) d 5.81 (ddt, J= 16.9, 10.1, 6.7 Hz, 1H), 5.55 (dtt, J= 15.3, 6.3, 1.3 Hz, 1H), 5.36 (dtt, J= 15.2, 6.8, 1.5 Hz, 1H), 4.99 (dq, J= 17.1, 1.7 Hz, 1H), 4.93 (ddt, J= 10.2, 2.2, 1.2 Hz, 1H), 4.07 (t, J= 6.9 Hz, 2H), 2.36 - 2.24 (m, 4H), 2.12 - 1.95 (m, 4H), 1.68 - 1.59 (m, 2H), 1.41 - 1.33 (m, 2H), 1.32 - 1.22 (m, 8H), 0.96 (t, J= 7.4 Hz, 3H). °C NMR (101 MHz, CDCb) d 174.04, 139.33, 135.14, 124.24, 1 14.28, 64.04, 34.52, 33.94, 32.13, 29.44, 29.36, 29.27, 29.21, 29.04, 25.77, 25.15, 13.89. MRMS (E+): [M] C17H30O2 Calculated - 266.2246, Found - 266.2239.

Reference： [1]Current Patent Assignee: CALIFORNIA INSTITUTE OF TECHNOLOGY - WO2019/113019, 2019, A2 Location in patent: Paragraph 198

84
[ 38460-95-6 ]
[ 116-85-8 ]
N-(4-hydroxy-9,10-dioxo-9,10-dihydroanthracen-1-yl)undec-10-enamide [ No CAS ]

Reference： [1]Microbial Pathogenesis,2020,vol. 138

85
[ 38460-95-6 ]
[ 121-71-1 ]
3-acetylphenyl undec-10-enoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86.7%	Stage #1: undec-10-enoyl chloride; 3-Hydroxyacetophenone In dichloromethane at -2℃; for 0.5h; Inert atmosphere; Stage #2: With triethylamine In dichloromethane at -2 - 20℃; for 4h; Inert atmosphere;	2.2.10. 3-Acetylphenyl 4-chlorobutanoate (10) General procedure: 7 mL of anhydrous CH2Cl2 was added into 50 mL three-necked flaskconcluding M-hydroxyacetophenone (0.136 g, 1.0 mmol) with N2 protectionbelow -2 °C, after dissolved, 0.15 mL of 4-chloroprene wasslowly added. After 30 min, 0.5 mL of anhydrous Et3N was added andslowly increase to room temperature for 4 h. Then monitored the reactionby TLC. Quenched with 4-5 mL of water, extracted with CH2Cl2(20 mL×3), washed with saturated brine and dried over anhydrousNa2SO4. The mixture was filtered and the solvent was evaporated todryness. Purified with flash column (eluting with 1:6 v/v ethyl acetate/petroleum ether) afforded white solid compound 10 for 0.21 g, yield87.6%. HRMS found m/z: 263.0 [M+Na]+. 1H NMR(300 MHz,CDCl3): δ7.83 (ddd, J=7.8 Hz, 1.8 Hz, 1.2 Hz, 1H, ArH), 7.67 (t,J=7.8 Hz, 1H, ArH), 7.49 (t, J=8.4 Hz, 1H, ArH), 7.30 (ddd,J=8.4 Hz, 2.4 Hz, 1.2 Hz, 1H, ArH), 3.69 (t, J=6.3 Hz, 2H, ClCH2),2.81 (m, 2H, COCH2), 2.60 (s, 3H, CH3), 2.23 (m, 2H, CH2). 13C NMR(75 MHz, CDCl3): δ196.9, 171.1, 150.8, 138.6, 129.7, 127.0, 125.9,121.3, 43.9, 31.2, 27.4, 26.7.

Reference： [1]Chang, Yiqun; Wang, Peng-Cheng; Ma, Hong-Ming; Chen, Si-Yu; Fu, Yu-Hang; Liu, Yuan-Yuan; Wang, Xuan; Yu, Guang-Chao; Huang, Tao; Hibbs, David E.; Zhou, Hai-Bo; Chen, Wei-Min; Lin, Jing; Wang, Chao; Zheng, Jun-Xia; Sun, Ping-Hua [European Journal of Pharmaceutical Sciences, 2019, vol. 140]

86
[ 38460-95-6 ]
[ 35836-73-8 ]
(-)-nopyl undec-10-enoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With dmap; triethylamine In tetrahydrofuran at 22℃; for 16h; Inert atmosphere;

Reference： [1]Tappin, Nicholas D. C.; Michalska, Weronika; Rohrbach, Simon; Renaud, Philippe [Angewandte Chemie - International Edition, 2019, vol. 58, # 40, p. 14240 - 14244][Angew. Chem., 2019, vol. 131, # 40, p. 14378 - 14382,5]

Type	HazMat fee for 500 gram (Estimated)
Excepted Quantity	USD 0.00
Limited Quantity	USD 15-60
Inaccessible (Haz class 6.1), Domestic	USD 80+
Inaccessible (Haz class 6.1), International	USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic	USD 100+
Accessible (Haz class 3, 4, 5 or 8), International	USD 200+

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CAS No. :	38460-95-6	MDL No. :	MFCD00000772
Formula :	C₁₁H₁₉ClO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MZFGYVZYLMNXGL-UHFFFAOYSA-N
M.W :	202.72	Pubchem ID :	38042
Synonyms :		Chemical Name :	10-Undecenoylchloride

Num. heavy atoms :	13
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.73
Num. rotatable bonds :	9
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	59.51
TPSA :	17.07 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.1 cm/s

[ CAS No. 38460-95-6 ] {[proInfo.proName]}

Quality Control of [ 38460-95-6 ]

Related Doc. of [ 38460-95-6 ]

Product Details of [ 38460-95-6 ]

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Physicochemical Properties

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[ 38460-95-6 ] Synthesis Path-Downstream 1~86

Related Functional Groups of
[ 38460-95-6 ]

Acyl Chlorides

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Log Po/w (iLOGP) :	3.23
Log Po/w (XLOGP3) :	4.84
Log Po/w (WLOGP) :	4.06
Log Po/w (MLOGP) :	3.16
Log Po/w (SILICOS-IT) :	4.17
Consensus Log Po/w :	3.89

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Log S (ESOL) :	-3.55
Solubility :	0.0569 mg/ml ; 0.00028 mol/l
Class :	Soluble
Log S (Ali) :	-4.93
Solubility :	0.00237 mg/ml ; 0.0000117 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-4.13
Solubility :	0.0149 mg/ml ; 0.0000733 mol/l
Class :	Moderately soluble

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	3.0
Synthetic accessibility :	2.28

Signal Word:	Danger	Class:	8
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:	3265
Hazard Statements:	H314	Packing Group:	Ⅱ
GHS Pictogram:

Precautionary Statements-General
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P370	In case of fire:
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P372	Explosion risk in case of fire.
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P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
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P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 38460-95-6 ] {[proInfo.proName]}

Quality Control of [ 38460-95-6 ]

Related Doc. of [ 38460-95-6 ]

Product Details of [ 38460-95-6 ]

Calculated chemistry of [ 38460-95-6 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 38460-95-6 ]

Application In Synthesis of [ 38460-95-6 ]

[ 38460-95-6 ] Synthesis Path-Downstream 1~86

Related Functional Groups of [ 38460-95-6 ]

Acyl Chlorides

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 38460-95-6 ]