文献类型：期刊文献

中文题名：邻氯苯甘氨酸甲酯的拆分研究

英文题名：Reserach on The Resolution of Chlorobenzene Glycine

作者：付文健[1];林美庆[1];贺雨晨[1];陈建中[1];赵敏[1]

机构：[1]华东理工大学化学与分子工程学院,上海200237

年份：2019

卷号：27

期号：2

起止页码：123

中文期刊名：合成化学

外文期刊名：Chinese Journal of Synthetic Chemistry

收录：CSTPCD;;北大核心:【北大核心2017】；

语种：中文

中文关键词：邻氯苯甘氨酸甲酯;化学拆分;pH电位滴定;非对映异构体;共振瑞利散射

外文关键词：2-chlorophenyl glycine methyl ester;chemical resolution;pH potentiometric titration;diastereoisomer;resonance Rayleigh scattering

摘要：以L-(+)-酒石酸作为手性拆分剂,苯甲醛作催化剂,对外消旋的邻氯苯甘氨酸甲酯混合物进行了化学拆分。S-(+)-邻氯苯甘氨酸甲酯的拆分收率达到93%,ee 99.96%,其结构经~1H NMR和HPLC确证。使用pH电位滴定法研究了邻氯苯甘氨酸甲酯与酒石酸形成的盐的稳定性,采用X-射线单晶衍射确定了一对非对映异构体盐的立体结构,并初步推测了非对映异构体的拆分机理。用共振瑞利散射分析了两种异构体盐结构。
The chemical resolution of S-(+)-o-chlorophenylglycine methyl ester was investigated by using L-(+)-tartaric acid as the chiral resolution agent and benzaldehyde as the catalyst.The resolution yield was 93%and ee was 99.96%.The stability of the salt of chlorophenol methyl esters and tartaric acid was studied with pH potentiometric titration.X-ray single crystal diffraction determines the three-dimensional structure of a pair of diastereomers,and the mechanism of splitting the diastereomer was preliminarily surmised.The structures of two isomer salts were analyzed by resonance Rayleigh scattering method.