通过卡迪奥特-乔德凯维茨偶联反应合成基于1,4-环己二烯的炔基大环化合物。一种管状四聚体容器的结构。

Synthesis of 1,4-cyclohexadiene-based acetylenic macrocycles with Cadiot-Chodkiewicz coupling. Structure of a tub-shaped tetrameric container.

作者信息

Bandyopadhyay Arkasish, Varghese Babu, Sankararaman Sethuraman

机构信息

Department of Chemistry, Indian Institute of Technology, Madras, Chennai-600036, India.

出版信息

J Org Chem. 2006 Jun 9;71(12):4544-8. doi: 10.1021/jo0605290.

DOI:10.1021/jo0605290

PMID:16749787

Abstract

The Cadiot-Chodkiewicz coupling of cis-1,4-diethynyl-1,4-dimethoxycyclohexa-2,5-diene and the corresponding ethynyl bromide gave a mixture of acetyenic macrocycles ranging from dimer to octamer in good isolable yields. The trimeric and tetrameric macrocycles have been structurally characterized by single-crystal X-ray crystallography. In the crystal structure of the trimeric macrocycle a molecule of benzene is sandwiched between a pair of macrocyles. The tetrameric macrocycle exhibited a tub-shaped conformation and encapsulated a molecule of ethyl acetate inside the tub.

摘要

顺式-1,4-二乙炔基-1,4-二甲氧基环己-2,5-二烯与相应的乙炔基溴进行卡迪奥-乔德凯维茨偶联反应，得到了一系列从二聚体到八聚体的乙炔大环化合物混合物，且产率良好，易于分离。三聚体和四聚体大环化合物已通过单晶X射线晶体学对其结构进行了表征。在三聚体大环化合物的晶体结构中，一个苯分子夹在一对大环之间。四聚体大环化合物呈现出桶状构象，并在桶内包封了一个乙酸乙酯分子。