摘要
为了拓展叶绿素类二氢卟吩的研究和应用,以焦脱镁叶绿酸-a甲酯为起始原料,通过氧化和缩合反应,对其N^(21)-N^(23)轴向两端的取代基团进行化学修饰和结构转换,在四吡咯大环分子的周环上构建了醛、邻位二酮、烯腈和烯酮等活性受电子官能结构,再与不同的富电子体系实施关环,合成了一系列未见报道的含有多种杂环结构的焦脱镁叶绿酸衍生物,其化学结构均经UV-Vis, IR, ~1H NMR, MS及元素分析予以证实.同时,对相应杂环的形成过程、立体化学选择性以及电子光谱变化进行了讨论.
In order to expand study and application for the chlorophllous chlorins, pyropheophorbide-a methyl ester was used as a starting material. The chemical modifications and structural transformations along the terminals of N21-N23 axis were carried out to build active electron-accepting functional structures such as aldehyde, α-diketone, enenitrile and ketene moieties. The cyclizations with different electron-sufficient systems were accomplished to synthesize a series of unreported chlorins related to chlorophyll with multiple heterocyclic structures. The chemical structures of new compounds were characterized by elemental analysis, MS, UV-Vis, IR and 1H NMR spectra. Meanwhile the relevant formation process of the heterocyclic ring, the stereochemistry selectivity and the change of the electronic spectrum were discussed.
作者
张珠
李家柱
张善国
王振
王进军
Zhang Zhu;Li Jiazhu;Zhang Shanguo;Wang Zhen;Wang Jinjun(Department of Food &Biological Engineering,Wenjing College,Yantai University,Yantai 264005;College of Chemistry and Chemical Engineering,Yantai University,Yantai 264005)
出处
《有机化学》
SCIE
CAS
CSCD
北大核心
2018年第12期3250-3259,共10页
Chinese Journal of Organic Chemistry
基金
国家自然科学基金(No.21272048)
山东省高校科技计划(No.J15LC51)资助项目~~
关键词
叶绿素-A
二氢卟吩
化学修饰
杂环化反应
合成
chlorophyll-a
chlorin
chemical modification
heterocyclization reaction
synthesis