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2014 , Vol. 34 >Issue 3: 552 - 560

DOI: https://doi.org/10.6023/cjoc201310002

研究论文

叶绿素降解产物的环丙基化及其二氢卟吩衍生物的合成

  • 刘洋 ,
  • 徐希森 ,
  • 李家柱 ,
  • 殷军港 ,
  • 祁彩霞 ,
  • 王进军
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  • a 烟台大学化学化工学院 烟台 264005;
    b 山东省黄金工程技术研究中心(工业应用) 烟台 264005

收稿日期: 2013-10-06

  修回日期: 2013-11-08

  网络出版日期: 2013-11-20

基金资助

国家自然科学基金（No. 21272048）和山东省黄金工程技术研究中心（2011年度）资助项目.

收起

Cyclopropylation of Chlorophyllous Degradation Products and Synthesis of Chlorin Derivatives

  • Liu Yang ,
  • Xu Xisen ,
  • Li Jiazhu ,
  • Yin Jungang ,
  • Qi Caixia ,
  • Wang Jinjun
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  • a College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005;
    b Shandong Applied Research Centre of Gold Nanotechnology (Au-SDARC), Yantai 264005

Received date: 2013-10-06

  Revised date: 2013-11-08

  Online published: 2013-11-20

Supported by

Project supported by the National Natural Science Foundations of China (No. 21272048) and the Project of Shandong Applied Reaearch Centre of Gold Nanotechnology (2011).

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摘要

以叶绿素降解产物脱镁叶绿酸-a甲酯为起始原料，利用其二氢卟吩大环上的活性反应区域，沿着N21-N23轴向进行官能团修饰，通过1，3-偶极环加成反应、Grignard反应和外接环的结构改造，在周环上的不同位置上引进了三元环烷基结构，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，其化学结构均经UV，IR，1H NMR，MS及元素分析予以证实，同时也讨论了环丙基的引进对二氢卟吩的理化性质所产生的各种影响，并对部分新化合物的体外光动力活性进行了测试.

关键词： 叶绿素-a; 二氢卟吩; 化学修饰; 环丙基化; 合成

本文引用格式

刘洋 , 徐希森 , 李家柱 , 殷军港 , 祁彩霞 , 王进军 . 叶绿素降解产物的环丙基化及其二氢卟吩衍生物的合成[J]. 有机化学, 2014 , 34(3) : 552 -560 . DOI: 10.6023/cjoc201310002

Abstract

Pheophorbide-a methyl ester, as a degraded product from chlorophyll-a, was used as a starting material, and the modifications for functional groups along N21-N23-axis were completed by making use of reactive regions. The tri-membered ring structures were introduced to the macrocyclic chromophore in different position by 1,3-polar cycloaddition, Grignard reaction and reconstructions for exocyclic ring. A series of unreported chlorins related to chlorophyll were synthesized and their chemical structures were characterized by UV, IR, 1H NMR, MS techniques and elemental analysis. The different effects on the physical and chemical properties of chlorophyllous chlorins by introduction of cyclopropyl group were discussed and in vitro photodynamic activities of some new compounds were determined.

Key words： chlorophyll-a; chlorin; chemical modification; cyclopropylation; synthesis

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