三萜烯衍生杯[5]芳烃的合成、结构和构象特征。

Synthesis, structures, and conformational characteristics of triptycene-derived calix[5]arenes.

机构信息

Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.

出版信息

Org Lett. 2010 Feb 5;12(3):524-7. doi: 10.1021/ol902758g.

DOI:10.1021/ol902758g

PMID:20067267

Abstract

A series of novel calix[5]arenes 5 containing one 1,8-dimethoxytriptycene moiety were synthesized through an efficient fragment coupling strategy. The subsequent demethylation of 5 with BBr(3) in dry dichloromethane gave the calix[5]arenes 6. Debutylation of both 5a-b and 6a-b with AlCl(3) resulted in the same products 7a-7b. The structural studies revealed that all of the macrocyclic compounds have well-defined structures with fixed cone conformations in both solution and solid state. Moreover, it was also found that the triptycene-derived calix[5]arenes could encapsulate small neutral molecules in the solid state.

摘要

通过高效的片段偶联策略，合成了一系列含有一个 1,8-二甲氧基三芴基部分的新型杯[5]芳烃 5。随后，用 BBr(3)在干燥的二氯甲烷中对 5 进行脱甲基化反应，得到杯[5]芳烃 6。用 AlCl(3)对 5a-b 和 6a-b 进行脱丁基化反应，得到相同的产物 7a-7b。结构研究表明，所有的大环化合物在溶液和固态中都具有确定的结构，呈固定的锥形构象。此外，还发现三芴基衍生的杯[5]芳烃在固态中可以包合小分子中性分子。