1-(2-氰乙基)-2-氧代环戊基甲酸甲酯的选择性水解脱羧  

Selective Hydrolysis and Decarboxylation of Methyl [1-(2-Cyanoethyl)-2-oxocyclopentyl]carboxylate

作　　者：赵广乐[1] 于亮[2] 闫喜龙[1] 王东华[2] 陈立功[1] 

机构地区：[1]天津大学化工学院,天津300072 [2]天津大学药物科学与技术学院,天津300072

出　　处：《有机化学》2009年第9期1440-1444,共5页Chinese Journal of Organic Chemistry

基　　金：河南省杰出人才创新基金(No.0521001500)资助项目

摘　　要：对1-(2-氰乙基)-2-氧代环戊基甲酸甲酯(4)的选择性水解脱羧反应进行了系统研究.发现上述化合物在碱的催化作用下主要生成开环副产物2-(2-氰乙基)己二酸二甲酯及2-(2-氰乙基)己二酸;由于氰基在酸性介质中也可发生水解,因此对1-(2-氰乙基)-2-氧代环戊基甲酸甲酯在酸性情况下水解脱羧的反应条件进行了探索,发现在4mol?L-1盐酸介质中,50℃下反应24h,以84.0%的收率得到目标产物3-(2-氧代环戊基)-丙腈.Selective hydrolysis and decarboxylation of methyl [1-（2-cyanoethyl）-2-oxocyclopentyl]- carboxylate （4） were studied. The ring-opened byproducts, dimethyl-2-（2-cyanoethyl）adipate and 2-（2-cyanoethyl）adipic acid, were obtained primarily in an alkaline medium. While, in an acid medium, the hydrolysis and decarboxylation of 4 were studied since the cyano group could also be hydrolyzed. 3-（2-Oxocyclopentyl）propanenitrile was yielded in 84.0% at 50 ℃ after 24 h in the medium of 4 mol·L^-1 HCl after optimization.

关 键 词：1-(2-氰乙基)-2-氧代环戊基甲酸甲酯 3-(2-氧代环戊基)-丙腈 水解 脱羧 

分 类 号：O621.25[理学—有机化学]