10-十一碳炔酸

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Glassware used for surface modification was cleaned with organic solvents and etched overnight in basic detergent solution. Prior to use, it was rinsed with ultrapure water and dried at 120° C. 1-Hexadecene (98%, Sigma-Aldrich) was purified by column chromatography and vacuum distillation. 1-Hexadecyne was obtained by reacting 1-bromotetradecane with lithium acetylide ethylenediamine complex in dimethylsulfoxide. 11-Fluoroundec-1-ene was synthesized as described elsewhere.14 2,2,2-Trifluoroethyl undec-10-ynoate and 2,2,2-trifluoroethyl undec-10-enoate were synthesized by esterification of 10-undecynoic acid, respectively 10-undecenoic acid, with 2,2,2-trifluoroethanol using N,N′-dicyclohexylcarbodiimide as a coupling reagent and 4-dimethylaminopyridine as a catalyst. Solvents used were either of analytical grade or distilled prior to use. distilled

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Glassware used for surface modification was cleaned with organic solvents and etched overnight in basic detergent solution. Prior to use, it was rinsed with ultrapure water and dried at 120° C. 1-Hexadecene (98%, Sigma-Aldrich) was purified by column chromatography and vacuum distillation. 1-Hexadecyne was obtained by reacting 1-bromotetradecane with lithium acetylide ethylenediamine complex in dimethylsulfoxide. 11-Fluoroundec-1-ene was synthesized as described elsewhere.14 2,2,2-Trifluoroethyl undec-10-ynoate and 2,2,2-trifluoroethyl undec-10-enoate were synthesized by esterification of 10-undecynoic acid, respectively 10-undecenoic acid, with 2,2,2-trifluoroethanol using N,N′-dicyclohexylcarbodiimide as a coupling reagent and 4-dimethylaminopyridine as a catalyst. Solvents used were either of analytical grade or distilled prior to use. distilled

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Methyl 10-undecynoate was prepared via the reaction of 10-undecynoic acid (Farchan) with diazomethane. The ester (1.6 g, 8 mmole) was hydroborated with catecholborane. The yield of the boronic acid was 1.7 g (87%); mp 48.5-50; mass spectrum, 316.9 (calcd. m/e316.1); NMR (CDCl3) 1.3 δ(broad s, 12H, alkane), 2.35 (broad envelope, 4H, --CH2CH=,--CH2CO2), 3.6 (s, 3H, --OCH3), 5.38 (d, 1H, --C=CHB, J=17 Hz), 6.4 (m, 1H, --CH=CHB).

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Methyl 10-undecynoate was prepared via the reaction of 10-undecynoic acid (Farchan) with diazomethane. The ester (1.6 g, 8 mmole) was hydroborated with catecholborane. The yield of the boronic acid was 1.7 g (87%); mp 48.5-50; mass spectrum, 316.9 (calcd. m/e316.1); NMR (CDCl3) 1.3 δ(broad s, 12H, alkane), 2.35 (broad envelope, 4H, --CH2CH=,--CH2CO2), 3.6 (s, 3H, --OCH3), 5.38 (d, 1H, --C=CHB, J=17 Hz), 6.4 (m, 1H, --CH=CHB).

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 36.45 g (200 mmol) of 10-undecynoic acid in 200 ml 1N NaOH at 0° C. was added a solution of alkaline sodium hypobromite dropwise over 30 minutes, maintaining the temperature below 5° C. (the hypobromite solution was prepared by the dropwise addition of 35.16 g (220 mmol) of bromine to 55 ml of 20N NaOH at 0°-5° C.). The mixture was stirred four hours at 0°-5° C., and was then acidified to pH 1 with 9M H2SO4. The solution was extracted with three 150 ml portions of ether. The combined extracts were dried (Na2SO4) and evaporated yielding 50.159 (96% crude) of a pale yellow solid. This was used without further purification. The solution was extracted with three 150 ml portions of ether The combined extracts were dried (Na2SO4) evaporated yielding 50.159 (96% crude) of a pale yellow solid This was used without further purification

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 36.45 g (200 mmol) of 10-undecynoic acid in 200 ml 1N NaOH at 0° C. was added a solution of alkaline sodium hypobromite dropwise over 30 minutes, maintaining the temperature below 5° C. (the hypobromite solution was prepared by the dropwise addition of 35.16 g (220 mmol) of bromine to 55 ml of 20N NaOH at 0°-5° C.). The mixture was stirred four hours at 0°-5° C., and was then acidified to pH 1 with 9M H2SO4. The solution was extracted with three 150 ml portions of ether. The combined extracts were dried (Na2SO4) and evaporated yielding 50.159 (96% crude) of a pale yellow solid. This was used without further purification. The solution was extracted with three 150 ml portions of ether The combined extracts were dried (Na2SO4) evaporated yielding 50.159 (96% crude) of a pale yellow solid This was used without further purification

反应条件: temp:0.00; pressure:0.00; stir:

实验步骤: 投料: 取100ml单口瓶，加入SM1，碳酸钾，加入DMF溶解，搅拌下滴加苄溴，滴加完毕后常温搅拌过夜。\n后处理: 加入水和EA萃取三次，合并有机相，干燥浓缩得无色油状粗品。\n监测: GCMS（280625-2-1）显示主峰为产物峰，M=272.\n纯化: 硅胶柱层析，PE/EA做流动相，3%EA出产物，收集浓缩得无色液体6.5g。HNMR（280625-2-1）确证为产物。

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 10-Undecynoic acid (21.8 g, 0.120 mol) was neutralized with a solution of 57 mL 10 percent KOH in water and hydroxylamine hydrochloride (0.380 g) was added. Then a catalyst consisting of a solution of 1.9 g cuprous chloride in 16 g 70 percent aqueous ethylamine was added. A yellow precipitate formed immediately. A solution of the crude 1-iodo-1-dodecyne in 40 mL methanol was then added dropwise with stirring. The suspension was stirred for one hour after the addition. The reaction mixture was acidified by the addition of 2.5N HCl, filtered, and the filtrate and precipitate washed with ether. The ether layers were washed with water, thiosulfate solution, water and saturated sodium chloride. After drying Na2SO4) the solvents were removed under reduced pressure. The residue was induced to crystallize by scratching under petroleum ether. The crystals of the diyne acid (26.4 g, 74%) exhibited m.p. 57°-58° after recrystallization from acetonitrile. was added was added A yellow precipitate formed immediately The suspension was stirred for one hour after the addition filtered the filtrate and precipitate washed with ether The ether layers were washed with water, thiosulfate solution, water and saturated sodium chloride After drying Na2SO4) the solvents were removed under reduced pressure to crystallize after recrystallization from acetonitrile

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 10-undecynoic acid (0.40 g, 2.2 mmol) in CH3CN (10 mL) was added O—(N-succinimidyl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (0.99 g, 3.29 mmol). After stirring for 2 min at RT, the reaction was quenched with 1% AcOH and diluted with CHCl3 (150 mL). The organic solution was then extracted with 1% AcOH (10 mL), rinsed with H2O (2×40 mL), then dried over Na2SO4. The solution was then decanted and concentrated. A quantitative yield was assumed and the material was taken on directly to the next step. TLC (10% MeOH/CHCl3) Rf=0.90, UV active. the reaction was quenched with 1% AcOH diluted with CHCl3 (150 mL) The organic solution was then extracted with 1% AcOH (10 mL) rinsed with H2O (2×40 mL) dried over Na2SO4 The solution was then decanted concentrated