研究论文

周环上芳基取代的叶绿素类二氢卟吩衍生物的合成

  • 于沙沙 ,
  • 徐希森 ,
  • 刘洋 ,
  • 李家柱 ,
  • 金英学 ,
  • 祁彩霞 ,
  • 王进军
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  • a 哈尔滨师范大学化学化工学院 哈尔滨 150025;
    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: 2013-07-31

  修回日期: 2013-10-11

  网络出版日期: 2013-10-25

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.

Synthesis of Chlorophyllous Chlorins Derivatives Substituted by Aromatic Groups on Their Periphery

  • Yu Shasha ,
  • Xu Xisen ,
  • Liu Yang ,
  • Li Jiazhu ,
  • Jin Yingxue ,
  • Qi Caixia ,
  • Wang Jinjun
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  • a College of Chemistry & Engineering, Harbin Normal University, Harbin 150025;
    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: 2013-07-31

  Revised date: 2013-10-11

  Online published: 2013-10-25

Supported by

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

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,对五元外接E-环也实施了结构改造,在周环上分别引进了能与大环色基形成不同共轭程度的芳香性取代基团,完成了12个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和质谱及元素分析予以证实,同时也讨论了芳基的引进对二氢卟吩的理化性质所产生的各种影响.

本文引用格式

于沙沙 , 徐希森 , 刘洋 , 李家柱 , 金英学 , 祁彩霞 , 王进军 . 周环上芳基取代的叶绿素类二氢卟吩衍生物的合成[J]. 有机化学, 2014 , 34(2) : 362 -370 . DOI: 10.6023/cjoc201307056

Abstract

Pyropheophorbide-a methyl ester, as a degraded product from chlorophyll-a, was used as a starting material, and the modifications for functional group along N21-N23-axis and reconstructions for five-membered exocyclic E-ring were completed to introduce different aromatic groups which could conjugated with macrocyclic chromophore at various degrees on the periphery. The syntheses of 12 unreported chlorins related to chlorophyll were accomplished and their chemical structures were characterized by elemental analysis, UV, IR, MS and 1H NMR spectra. The different effects on the physical and chemical properties of chlorophyllous chlorins by introduction of aromatic groups were discussed.

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