马来海松酸二酰亚胺的合成及其构象

doi:10.3969/j.issn.1007-2985.2014.01.015

journal6 ›› 2014, Vol. 35 ›› Issue (1): 63-67.DOI: 10.3969/j.issn.1007-2985.2014.01.015

马来海松酸二酰亚胺的合成及其构象

王恒山，李剑飞，覃坚妹，朱永涛，叶鳗仪，李亚军，姚贵阳

（广西师范大学化学与药学学院，药用资源化学与药物分子工程重点实验室，广西桂林 541004）

出版日期:2014-01-25 发布日期:2014-01-25
作者简介:王恒山(1965-)，男，浙江温州人，广西师范大学化学与药学学院教授，博士，主要从事手性药物抗肿瘤活性研究.
基金资助:
国家自然科学基金资助项目(81260472，21101035)；973计划前期研究专项(2011CB512005)；广西自然科学基金资助项目(2011GXNSFD018010，2010GXNSFF013001)

Synthesis and Conformation of Maleopimaric Acid Diimide

WANG Heng-Shan, LI Jian-Fei, QIN Jian-Mei, ZHU Yong-Tao, YE Man-Yi, LI Ya-Jun, YAO Gui-Yang

(Key Laboratory for the Chemistry and Molecular Engineering of Medicinal Resources,School of Chemistry & Pharmacy of Guangxi Normal University,Guilin 541004,Guangxi China)

Online:2014-01-25 Published:2014-01-25

摘要/Abstract

摘要：以一级松香与马来酸酐的Diels-Alder加成产物马来海松酸及其进一步甲酯化产物马来海松酸甲酯为反应原料，制备了1个新型N-芳香基马来海松酸二酰亚胺.化合物的结构均经元素分析、NMR和MS表征，用COSY，HMQC和HMBC进一步对新型N-芳香基马来海松酸二酰亚胺进行结构分析，首次发现松香背景的衍生物在溶剂中能够进行构型的动力学翻转，并利用2D NMR确定了其trans和cis在溶液中的构象.

关键词： 位阻异构, 马来海松酸二酰亚胺, 合成, 构象

Abstract: Maleopimaric acid (compound 2) was formed by Diels-Alder addition of maleic acid anhydride to resin acid,then maleopimaric acid methyl ester (compound 3) was prepared by esterification of dimethyl sulfate.After maleopimaric acid methyl ester interacting with 5-Aminoisoquinoline,the N-aryl methyl maleopimaric acid diimides (compound 4) was obtained.The structures of all compounds were characterized by elemental analyses,NMR and MS.Atropisomerism was first found in compound 4 in CDCl3,and the proportion of different atropisomer(trans:cis) was calculated by 2D NMR.

Key words: atropisomerism, maleopimaric acid diimide, synthesis, conformation

王恒山, 李剑飞, 覃坚妹, 朱永涛, 叶鳗仪, 李亚军, 姚贵阳. 马来海松酸二酰亚胺的合成及其构象[J]. journal6, 2014, 35(1): 63-67.

WANG Heng-Shan, LI Jian-Fei, QIN Jian-Mei, ZHU Yong-Tao, YE Man-Yi, LI Ya-Jun, YAO Gui-Yang. Synthesis and Conformation of Maleopimaric Acid Diimide[J]. journal6, 2014, 35(1): 63-67.

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马来海松酸二酰亚胺的合成及其构象

Synthesis and Conformation of Maleopimaric Acid Diimide

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