酪氨酸基柱[5]芳烃的合成及手性识别性能初探  

Synthesis and chiral recognition of tyrosinefunctionalized column [5] arene reagent

作　　者：何琴 马翠广 段文贵[1] 刘陆智[1] HE Qin;MA Cuiguang;DUAN Wengui;LIU Luzhi(School of Chemistry and Chemical Engineering,Guangxi University,Nanning 530004,China)

机构地区：[1]广西大学化学化工学院,广西南宁530004

出　　处：《广西大学学报（自然科学版）》2023年第2期442-450,共9页Journal of Guangxi University（Natural Science Edition）

基　　金：国家自然科学基金项目(21967004)

摘　　要：针对作为当前的前沿主体分子,柱芳烃的手性性能研究已成为科研工作者的热门研究课题,但在客体分子的手性识别特别是在对映体纯度和绝对构型确定的应用却寥寥无几的问题,本文设计合成了2种新型酪氨酸基柱[5]芳烃D-MPC-8和L-MPC-8作为手性溶剂化试剂(CSA),并通过1H NMR研究了它们对手性模板客体α萘乙胺的手性性能。结果表明:柱[5]芳烃对α萘乙胺(G1)具有良好的手性识别,并且在柱芳烃立体异构体存在的情况下,R和S构型之间的非等效质子的NMR信号完全相反,据此建立一种简单的方法并成功地确定了G1的绝对构型。To address the problem that the chiral properties of pillar[n]arenes,which are the current frontier subject molecules,have become a popular research topic among researchers,but there are few applications in the chiral identification of guest molecules,especially in the enantiomeric purity and absolute conformation determination,two new tyrosine-based pillar[5]arenes,D-MPC-8 and L-MPC-8,were designed and synthesized as chiral solvating agents(CSAs)in this paper.And their chiral properties of the chiral template guestα-naphthyl ethylamine were investigated by 1H NMR.The results show that pillar[5]arenes have good chiral recognition forα-naphthalene ethylamine,and the NMR signals of non equivalent protons between R and S configurations are completely opposite in the presence of pillar[5]arenes stereoisomers.Therefore,this can be used to establish a simple method to successfully determine the absolute configuration of G1.

关 键 词：柱芳烃 手性识别 合成 

分 类 号：O625[理学—有机化学]