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2012 , Vol. 32 >Issue 02: 360 - 367

DOI: https://doi.org/10.6023/cjoc1108301

研究论文

多酯基取代的叶绿素类二氢卟吩衍生物的合成

  • 殷军港 ,
  • 王振 ,
  • 杨泽 ,
  • 刘超 ,
  • 赵丽丽 ,
  • 王进军
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  • a 烟台大学化学化工学院 烟台 264005;
    b 烟台大学药学院 烟台 264005

收稿日期: 2011-08-30

  修回日期: 2011-10-09

  网络出版日期: 2012-03-09

基金资助

山东省自然科学基(No. Y2008B49)、中匈政府间科技合作(No. 2008-444-4-32)资助项目.

收起

Synthesis of Multi-ester Substitutied Chlorin Derivatives Related to Chlorophyll-a

  • YIN Jun-Gang ,
  • WANG Zhen ,
  • YANG Ze ,
  • LIU Chao ,
  • ZHAO Li-Li ,
  • WANG Jin-Jun
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  • a Colledge of Chemistry and Chemical Engineering, Yantai University, Yantai 264005;
    b Pharmacy College, Yantai University, Yantai 264005

Received date: 2011-08-30

  Revised date: 2011-10-09

  Online published: 2012-03-09

Supported by

Project supported by the Natural Science Foundation of Shandong Province of China (No. Y2008B49) and the International Science and Technology Project between Governments of China and Hungary (No. 2008-444-4-32).

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摘要

以脱镁叶绿酸-a 甲酯为起始原料, 通过碱性条件下的水解开环、空气氧化和重排反应, 分别合成了红紫素-7 三甲酯和二氢卟吩-p6 三甲酯. 然后对其C(3)-乙烯基、20-meso-位、12-位甲基以及尾端酯基进行化学修饰, 通过亲电加成、亲电取代、1,3-偶极环加成和氧化重排等反应, 完成10 种具未见报道的的叶绿素类二氢卟吩衍生物, 其化学结构均经UV, IR, 1H NMR 光谱及元素分析予以表征.

关键词： 叶绿素-a; 脱镁叶绿酸-a 甲酯; 叶绿素降解; 二氢卟吩; 化学修饰; 合成

本文引用格式

殷军港 , 王振 , 杨泽 , 刘超 , 赵丽丽 , 王进军 . 多酯基取代的叶绿素类二氢卟吩衍生物的合成[J]. 有机化学, 2012 , 32(02) : 360 -367 . DOI: 10.6023/cjoc1108301

Abstract

From methyl pheophorbide-a which was used as a starting material, purpurin-7 trimethyl ester and chlorin-p6 trimethyl ester were synthesized by hydrogation-opening ring, allomerization and rearrangement reaction. The synthesis of ten unreported chlorin derivatives related to chlorophyll-a was accomplished by electrophilic adduction, electrophilic substitution, 1,3-dipolar cycloadduction and oxidation-rearrangement reaction to chemical modifications for C(3)-vinyl group, 20-meso-position, methyl group at 12-position and ester moieties at terminal positions. The structures of all new chlorins were characterized by UV, IR, 1H NMR spectra and elemental analysis.

Key words： chlorophyll-a; methyl pheophorbide-a; chlorophyll degradation; chlorin; chemical modification; synthesis

参考文献

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