环己酮与丙烯酸甲酯及(S)-3-(2′-氧环己基)-丙酸与醇的酯化反应  

Esterifications of Cyclohexanone with Methyl Acrylate and (S)-3-(2′-Oxocyclohexyl)-propionic Acid with Alcohols

作　　者：王会萍[1] 商艳梅[1] 王磊[1] 李叶芝[1] 黄化民[1] 

机构地区：[1]吉林大学化学学院

出　　处：《高等学校化学学报》2006年第5期894-896,共3页Chemical Journal of Chinese Universities

基　　金：国家自然科学基金(批准号:20172019)资助

摘　　要：The esterification of carboxylic acid with alcohol in the presence of catalytic amounts of mineral acids is one of the most methods for preparing esters.The catalysts generally preferred are sulfuric acid or p-toluenesulfonic acid.But the products esters were racemic when（S）-3-（2′-oxocyclohexyl） propionic acid reacts with alcohols in the presence of sulfuric acid or with p-toluenesulfonic acid as catalyst.We replace sulfuric acid with Fe2(SO4)3·xH2O as the catalyst.The optical compound（S）-methyl-3-（2′-oxocyclohexyl）propionate,（（S）-ethyl-3-）（2′-oxocyclohexyl）propionate and（S）-n-butyl-3-（2′-oxocyclohexyl）propionate were obtained.In this paper we also reported that cyclohexanone reacted with methyl acrylate in the presence of potassium thiazolidine-2-thione-4-carboxylate（R）TTCA·K as the chiral catalyst to afford optically active（S）-3-（2′-oxocy-clohexyl） propionate.The mechanism of reaction of cyclohexanone with methyl acrylate in the presence of（R）TTCA·K as the catalyst would be a complex process.The esterification of carboxylic acid with alcohol in the presence of catalytic amounts of mineral acids is one of the most methods for preparing esters. The catalysts generally preferred are sulfuric acid or ptoluenesulfonic acid. But the products esters were racemic when （S）-3-（2＇-oxocyclohexyl） propionic acid reacts with alcohols in the presence of sulfuric acid or with p-toluenesulfonic acid as catalyst. We replace sulfuric acid with Fe2 （SO4 ）3· xH2O as the catalyst. The optical compound （S）-methyl-3-（2 ＇-oxocyclohexyl）propionate, （S） -ethyl-3- （ 2＇-oxocyclohexyl ） propionate and （ S ） -n-butyl-3-（ 2＇-oxocyclohexyl ） propionate were obtained. In this paper we also reported that cyclohexanone reacted with methyl acrylate in the presence of po- tassium thiazolidine-2-thione-4-carboxylate （R）TTCA· K as the chiral catalyst to afford optically active （S）- 3-（2＇-oxocy-clohexyl） propionate. The mechanism of reaction of cyclohexanone with methyl acrylate in the presence of （R）TTCA . K as the catalyst would be a complex process.

关 键 词：Fe2(SO4)3·xH2O 光活性3-(2′-氧环己基)-丙酸甲酯 光活性3-(2′-氧环己基)-丙酸乙酯 光活性3一(2’-KNg~)一丙酸丁酯 (R)-四氢噻唑-2-硫酮-4-羧酸钾盐 

分 类 号：O621[理学—有机化学]