摘要/Abstract

以焦脱镁叶绿酸-a甲酯及其N²¹-N²³轴向酰化和烯化的衍生物为起始原料，环上碳碳双键或碳氧双键与重氮烷发生1，3-偶极环加成、Michael加成和Tiffeneau-Demjanov重排反应，在周环上的不同位置上形成新的杂环和羰基结构，完成了一系列未见报道的叶绿素类二氢卟吩衍生物的合成.同时，基于相应的反应机理，讨论了重排过程的区域和立体选择性.
关键词: 叶绿素-a, 二氢卟吩, 焦脱镁叶绿酸, 重氮烷, 重排反应
Pyropheophorbide-a methyl ester and its derivatives acidylated and alkenylated along the N²¹-N²³ axis were used as starting materials. The 1,3-dipolar cyclocaddition, Michael addition and Tiffeneau-Demjanov rearrangement reaction can smoothly occur with diazoalkane through the carbon-oxygen or carbon-carbon double bonds attached to the periphery to generate new heterocyclic and carbonylic structures in different positions. The synthesis of a series of unreported chlorins related to chlorophyll was accomplished and their chemical structures were characterized by elemental analysis, UV-Vis, IR, MS and ¹H NMR spectra. Meanwhile, the region-and stereo-selectivities of rearrangement processes were discussed based on relevant reaction mechanism.
Key words: chlorophyll-a, chlorin, pyropheophorbide, diazoalkane, rearrangement reaction


PDF全文下载地址:

点我下载PDF