手性芳酰胺类分子钳的设计与微波合成

Design and Synthesis of Chiral Aromatic Amide Molecular Tweezers under Microwave Irradiation

以间苯二甲酸为隔离基,酰胺键桥联L-氨基酸甲酯构成手臂,在微波辐射下合成了具有不同手性中心和裂穴的新型手性芳酰胺类分子钳.结构均经1HNMR,IR及元素分析确证,并考察了其对芳香胺类化合物和D/L-氨基酸甲酯的识别性能.初步研究表明,这类分子钳受体不仅对中性小分子具有优良的识别性能,其结合常数(Ka)可达2.66×103L?mol-1,而且对D/L-氨基酸甲酯亦具有良好的手性识别能力.

A series of novel aromatic amide molecular tweezers with different chiral centers and cavities were designed and synthesized by using isophthalic acid as the spacer to bridge the different L-amino acid methyl esters under microwave irradiation. Their structures were characterized by H-1 NMR, IR spectra and elemental analysis. Their recognition properties for aromatic amines and methyl esters of amino acids were investigated. The preliminary results indicate that these chiral molecular tweezers not only recognize neutral molecules with a stability constant up to 2.66 X 10(3) L center dot mol(-1), but also show good enantioselectivity for D/L-amino acid methyl esters.