L-脯氨酸拆分1,1′-联-2-萘酚的实验设计  

Experimental design for chiral resolution of 1,1′-bi-2-naphthols with L-proline

作　　者：胡晓允[1] 李康 周忠强[1] 张道洪[1] HU Xiaoyun;LI Kang;ZHOU Zhongqiang;ZHANG Daohong(College of Chemistry and Materials,South-Central University for Nationalities,Wuhan 430074,China)

机构地区：[1]中南民族大学化学与材料科学学院,湖北武汉430074

出　　处：《实验室科学》2023年第4期10-13,共4页Laboratory Science

基　　金：湖北省一流本科课程《有机化学》(项目编号:YLKCS20012);湖北省优秀基层教学组织项目(项目编号:JCZZS2002);中南民族大学重点教研项(项目编号:JYZD22014)。

摘　　要：为了将手性化合物的包结拆分法引入有机化学实验教学,设计了有机化学综合实验“L-脯氨酸拆分1,1′-联-2-萘酚”:将L-脯氨酸和外消旋联萘酚研磨后,乙腈回流后析出L-脯氨酸和(S)-BINOL形成的包合物,(R)-BINOL留在溶液中。该综合实验实现了光学纯联萘酚的高效拆分,创新了教学体系。实践表明,该综合实验采用基于非共价键作用的包结拆分法进行手性拆分,激发了学生的学习兴趣;此外,该实验综合性强,有利于学生动手操作能力、分析和解决综合问题能力的培养。In order to bring the concept of enantioselective inclusion complexation into basic organic chemistry experiment teaching,chiral resolution of 1,1′-bi-2-naphthols with L-proline was designed.An improved method of chiral resolution of rac-BINOLs was developed.Rac-BINOL and L-proline were ground and refluxed in acetonitrile,and the resulting white precipitate was recrystallized in ethanol to improve the optical purity of(S')-BINOL and shorten the reaction time.The improved method could furnish BINOL enantiomer with>99%ee efficiently.This designed experiment is comprehensive,it not only stimulates students’interest in learning with novel teaching models,but also helps them develop their ability to analyze and solve practical problems.

关 键 词：包结拆分 L-脯氨酸 1 1′-联-2-萘酚 

分 类 号：O621.3[理学—有机化学]