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2014 , Vol. 34 >Issue 6: 1138 - 1147

DOI: https://doi.org/10.6023/cjoc201401007

研究论文

具有立体异构特征的叶绿素类二氢卟吩衍生物的合成

  • 纪建业 ,
  • 夏尚文 ,
  • 刘洋 ,
  • 殷军港 ,
  • 祁彩霞 ,
  • 王进军
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  • a. 通化师范学院化学系 通化 134002;
    b. 烟台大学化学化工学院 烟台 264005;
    c. 山东省黄金工程技术研究中心工业应用 烟台 264005

收稿日期: 2014-01-06

  修回日期: 2014-02-18

  网络出版日期: 2014-03-03

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

Synthesis of Chlorophyllous Chlorin Derivatives Possessing Stereo-isomeric Character

  • Ji Jianye ,
  • Xia Shangwen ,
  • Liu Yang ,
  • Yin Jungang ,
  • Qi Caixia ,
  • Wang Jinjun
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  • a. Department of Chemistry, College of Teachers, Tonghua 134002;
    b. College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005;
    c. Shandong Applied Research Centre of Gold Nanotechnology Au-SDARC, Yantai 264005

Received date: 2014-01-06

  Revised date: 2014-02-18

  Online published: 2014-03-03

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

以脱镁叶绿酸-a甲酯为起始原料，利用周环上的碳碳、碳氧和烯醇式复健，通过加成、取代、缩合和空气氧化等化学反应在色基上构建手性中心、顺反结构和阻旋位点. 经过旨在扩大立体差异的化学修饰，对部分差向异构体进行了有效分离，完成一系列具有立体异构特征的叶绿素衍生物的合成，并通过UV，IR，1H NMR及元素分析证实了11个未见报道的二氢卟吩衍生物的化学结构，同时对不同立体异构的形成及其表征进行了讨论.

关键词： 叶绿素-a; 二氢卟吩; 立体异构; 分离; 化学反应

本文引用格式

纪建业 , 夏尚文 , 刘洋 , 殷军港 , 祁彩霞 , 王进军 . 具有立体异构特征的叶绿素类二氢卟吩衍生物的合成[J]. 有机化学, 2014 , 34(6) : 1138 -1147 . DOI: 10.6023/cjoc201401007

Abstract

Pheophorbide-a methyl ester was used as a starting material, and chiral center, cis-trans structure and atropisomic position were established on the chromophore making use of carbon-carbon, carbon-oxygen and enol form double bond. A series of synthesis of chlorophyllous derivatives possessing stereo-isomeric character were completed by addition, substitution, condensation and allomerization. The part of epimers were separated from each other effectively after chemical modification for expanding stereo-differences. The chemical structures of 11 unreported chlorins related to chlorophyll were characterized by elemental analysis, UV, IR and 1H NMR spectra. The formations of different steric isomerism and their identifications were also discussed.

Key words： chlorophyll-a; chlorin; steric isomerism; separation; chemical reaction

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