三氟氯菊酸的手性拆分

摘要通过R（+）-α-苯乙胺与三氟氯菊酸在不同反应溶剂中反应，实现了对三氟氯菊酸的手性拆分。研究结果表明，当甲醇作反应溶剂时，R（+）-α-苯乙胺会与三氟氯菊酸络合形成包结物。所得晶体经FT-IR、¹H NMR以及X射线单晶衍射等测试分析手段表征，得出结论：与R（+）-α-苯乙胺形成包结物的三氟氯菊酸立体异构体为Z-（1S，S）-顺式-2，2-二甲基-3-（2-氯-3，3，3-三氟-1-丙烯基）环丙烷羧酸。

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	朱国华
	张明杰
	刘成鑫

关键词：三氟氯菊酸；手性拆分；包结物

Abstract： The chiral resolution of cis-3-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropan ecarboxylic acid was achieved by the reaction of R(+)-α-phenylethylamine with cis-3-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropanecarboxylic acid in different reaction solvents. The results show that when methanol is used as the reaction solvent, R(+)-α-phenylethylamine is complexed with cis-3-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropanecarboxylic acid to form heterocomplexatio. The obtained crystals were characterized by FT-IR, ¹H NMR and X-ray single crystal diffraction. Finally, it is concluded that the cis-3-(2-chloro-3,3,3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropanecarboxylic acid stereoisomers that form crystals with R(+)-α-phenylethylamine is Z-(1S,S)-cis-2,2-dimethyl-3-(2-chloro-3,3,3-trifluoro-1-propenyl) cyclopropanecarboxylic acid.

Keywords： cis-3-(2-chloro-3,3-trifluoroprop-1-en-1-yl)-2； 2-dimethylcyclopropanecarboxylic； chiral resolution； heterocomplexatio

Received 2017-07-12;

Corresponding Authors: 张明杰,E-mail:mjzhangtju@163.com。 Email: mjzhangtju@163.com

About author: 朱国华(1990-),女,硕士研究生,研究方向为有机合成。

引用本文:

朱国华, 张明杰, 刘成鑫.三氟氯菊酸的手性拆分[J]. 化学工业与工程, 2019,36(2): 34-37

Zhu Guohua, Zhang Mingjie, Liu Chengxin.A Chiral Resolution of Cis-3-(2-Chloro-3,3, 3-trifluoroprop-1-en-1-yl)-2,2-dimethylcyclopropanecarboxylic Acid[J]. Chemcial Industry and Engineering, 2019,36(2): 34-37

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