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邻氯苯甘氨酸甲酯的拆分研究

Reserach on The Resolution of Chlorobenzene Glycine

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【作者】 付文健林美庆贺雨晨陈建中赵敏

【Author】 FU Wen-jian;LIN Mei-qing;HE Yu-chen;CHEN Jian-zhong;ZHAO Min;College of Chemistry and Molecular Engineering, East China University of Science and Technology;

【通讯作者】 赵敏;

【机构】 华东理工大学化学与分子工程学院

【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。

【Abstract】 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.

  • 【文献出处】 合成化学 ,Chinese Journal of Synthetic Chemistry , 编辑部邮箱 ,2019年02期
  • 【分类号】O625.523
  • 【被引频次】2
  • 【下载频次】158
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