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通过连接两个碗状杯[3]芳烃酰胺部分合成的圆柱形大环化合物：结构和手性光学性质

Cylindrical macrocyclic compounds synthesized by connecting two bowl-shaped calix[3]aramide moieties: structures and chiroptical properties.

作者信息

Sakagami Ryoko, Saito Yuuki, Mori Ryuichi, Satake Misa, Okayasu Misaki, Kikkawa Shoko, Hikawa Hidemasa, Azumaya Isao

机构信息

Faculty of Pharmaceutical Sciences, Toho University 2-2-1 Miyama Funabashi Chiba 274-8510 Japan

出版信息

RSC Adv. 2020 Sep 18;10(57):34549-34555. doi: 10.1039/d0ra07060b. eCollection 2020 Sep 16.

DOI:10.1039/d0ra07060b
PMID:35514401
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9056864/
Abstract

Calix[3]aramide-based macrocycles 1 were successfully synthesized by a Glaser coupling reaction of two -calix[3]aramide moieties that have three ethynyl groups. The obtained macrocycles have stereoisomers: an enantiomeric pair and a form based on a combination of amide bond directions in the calix[3]aramide moieties at both ends of the molecule. Characteristic absorption spectra derived from the 1,4-diphenylbutadiyne structure were observed, while their ECD spectra were mirror-images. Single-crystal X-ray analysis revealed that each stereoisomer had a cylindrical rigid shape, and the absolute structure of the chiral-form was also assigned by comparing the Flack parameters. Mirror-image VCD spectra were observed for the enantiomeric chiral forms, and a VCD signal pattern of one enantiomer corresponded to that predicted by the relationship between the dihedral angle of the pair of C[double bond, length as m-dash]O groups.

摘要

基于杯[3]芳烃的大环化合物1通过两个具有三个乙炔基的杯[3]芳烃部分的格拉泽偶联反应成功合成。所得到的大环化合物具有立体异构体：一对对映体和一种基于分子两端杯[3]芳烃部分中酰胺键方向组合的形式。观察到源自1,4 - 二苯基丁二炔结构的特征吸收光谱，而它们的电子圆二色光谱（ECD）是镜像。单晶X射线分析表明，每个立体异构体都具有圆柱形刚性形状，并且通过比较弗拉克参数也确定了手性形式的绝对结构。观察到对映体手性形式的镜像振动圆二色光谱（VCD），并且一种对映体的VCD信号模式与由一对C = O基团的二面角之间的关系预测的模式相对应。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2ca/9056864/fcf9452f73f8/d0ra07060b-f8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2ca/9056864/fcee66b323a9/d0ra07060b-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2ca/9056864/616f723dfc7b/d0ra07060b-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2ca/9056864/51105fbb72db/d0ra07060b-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2ca/9056864/cd9b3400407b/d0ra07060b-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2ca/9056864/d07a8d1b8041/d0ra07060b-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2ca/9056864/dcf68e8935a4/d0ra07060b-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2ca/9056864/127952af8f86/d0ra07060b-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2ca/9056864/f067bf9c8809/d0ra07060b-f7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2ca/9056864/fcf9452f73f8/d0ra07060b-f8.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2ca/9056864/fcee66b323a9/d0ra07060b-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2ca/9056864/616f723dfc7b/d0ra07060b-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2ca/9056864/51105fbb72db/d0ra07060b-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2ca/9056864/cd9b3400407b/d0ra07060b-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2ca/9056864/d07a8d1b8041/d0ra07060b-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2ca/9056864/dcf68e8935a4/d0ra07060b-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2ca/9056864/127952af8f86/d0ra07060b-f6.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2ca/9056864/f067bf9c8809/d0ra07060b-f7.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d2ca/9056864/fcf9452f73f8/d0ra07060b-f8.jpg

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