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2013 , Vol. 33 >Issue 11: 2357 - 2366

DOI: https://doi.org/10.6023/cjoc201305006

研究论文

红紫素-18的周环结构修饰及其叶绿素类二氢卟吩衍生物的合成

  • 梁波颖 ,
  • 刘洋 ,
  • 徐希森 ,
  • 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: 2013-05-03

  修回日期: 2013-07-14

  网络出版日期: 2013-07-19

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.

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Modifications for Peripheral Structures of Purpurin-18 and Synthesis of Chlorophyllous Chlorin Derivatives

  • Liang Boying ,
  • Liu Yang ,
  • Xu Xisen ,
  • Jin Yingxue ,
  • Qi Caixia ,
  • Wang Jinjun
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  • a College of Chemistry & Chemical 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: 2013-05-03

  Revised date: 2013-07-14

  Online published: 2013-07-19

Supported by

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

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摘要

以红紫素-18甲酯为起始原料，利用其3-位乙烯基的多电子性，通过氧化、还原、亲电加成和1，3-偶极环加成等反应，对其N21-N23轴的端向结构进行化学修饰，在周环的3-位上引进了能与大环色基以不同方式形成共轭效应的取代基团，完成了11个未见报道具有红紫素-18碳架的叶绿素类二氢卟吩衍生物的合成，其化学结构均经UV，1H NMR，IR及元素分析予以证实； 讨论了红紫素-18的周环结构对其电子光谱所产生的影响，并对相应的化学反应提出了可能的反应机理.

关键词： 叶绿素-a; 二氢卟吩; 红紫素-18; 化学修饰; 合成

本文引用格式

梁波颖 , 刘洋 , 徐希森 , 金英学 , 祁彩霞 , 王进军 . 红紫素-18的周环结构修饰及其叶绿素类二氢卟吩衍生物的合成[J]. 有机化学, 2013 , 33(11) : 2357 -2366 . DOI: 10.6023/cjoc201305006

Abstract

Purpurin-18 methyl ester was used as a starting material, and the modifications for the structure on the terminal of its N21-N23-axis were completed making use of electron-richous properties of C (3)-vinyl group by various reactions including oxidation, reduction, electrophilic addition and 1, 3-polar cycloaddition. The substituted groups, which could conjugated with macrocyclic chromophore in different form, were introduce to 3-position on the periphery, respectively. The synthesis of 11 unreported chlorophyllous chlorins with basic skeloton of purpurin-18 was accomplished and their chemical structures were characterized by elemental analysis, UV, IR and 1H NMR spectra. The influence of peripheric structure of purpurin-18 on their electronic spectrum was discussed and the possible mechanisms about corresponding reactions were tentatively proposed.

Key words： chlorophyll-a; chlorin; purpurin-18; chemical modification; synthesis

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