手性杯[4]芳烃衍生物的合成及其在羧酸对映体识别中的应用。

Synthesis of chiral calix[4]arenes bearing aminonaphthol moieties and their use in the enantiomeric recognition of carboxylic acids.

机构信息

Department of Chemistry, Selçuk University, 42099, Konya, Turkey.

出版信息

Org Biomol Chem. 2011 Jan 21;9(2):571-80. doi: 10.1039/c0ob00399a. Epub 2010 Nov 10.

Abstract

Two armed chiral calix[4]arenes 8-16 functionalized at the lower rim with chiral aminonaphthol units have been prepared and the structures of these receptors characterized by FTIR, (1)H, and (13)C, DEPT and COSY NMR spectroscopy and elemental analysis. The enantioselective recognition of these receptors with various carboxylic acids has been studied by (1)H NMR and UV/Vis spectroscopy. The receptors exhibited different chiral recognition abilities towards the enantiomers of racemic materials and formed 2 : 1 or 1 : 1 complexes between host and guest. It was also demonstrated that chiral calix[4]arenes 9 and 16 could be used as chiral NMR solvating agents to determine the enantiomeric purity of mandelic acid.

摘要

两个手性杯[4]芳烃 8-16 在其下边缘用手性氨基萘酚单元进行了功能化，通过傅里叶变换红外光谱（FTIR）、（1）H 和（13）C、DEPT 和 COSY NMR 光谱以及元素分析对这些受体的结构进行了表征。通过（1）H NMR 和紫外/可见光谱研究了这些受体对各种羧酸的对映选择性识别。这些受体对消旋材料的对映异构体表现出不同的手性识别能力，并在主体和客体之间形成 2:1 或 1:1 配合物。还证明手性杯[4]芳烃 9 和 16 可用作手性 NMR 溶剂化试剂来确定扁桃酸的对映体纯度。