Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (6): 1294-1301.DOI: 10.6023/cjoc201410047 Previous Articles     Next Articles



李晶华a, 程建军a, 张朋c, 武进c, 金英学a, 王进军b,c   

  1. a 哈尔滨师范大学化学化工学院 哈尔滨 150025;
    b 烟台大学文经学院 烟台 264005;
    c 烟台大学化学化工学院 烟台 264005
  • 收稿日期:2014-10-31 修回日期:2015-01-20 发布日期:2015-02-02
  • 通讯作者: 金英学
  • 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.

Chemical Reaction of C(17)-End Ester Group in Pyropheophorbide and Synthesis of Chlorin Derivatives

Li Jinghuaa, Cheng Jianjuna, Zhang Pengc, Wu Jinc, Jin Yingxuea, Wang Jinjunb,c   

  1. a College of Chemistry and Chemical Engineering, Harbin Normal University, Harbin 150025;
    b Wenjing College, Yantai University, Yantai 264005;
    c College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005
  • Received:2014-10-31 Revised:2015-01-20 Published:2015-02-02
  • 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).

Pyropheophorbide-a methyl ester was used as a starting material. The active reaction regions were constructed by chemical modifications on the five-membered exocyclic ring, and the interconnections through different carbon chain between 132- and 17-position were carried out by classic reaction, such as intramolecular interesterification, Michael addition and Claisen condensation, to form bicyclic or spirocyclic structures in the side of C-D ring. The aminolysis and acylation were performed making use of chemical activity of end ester group at 17-position to establish the different chemical structures in the far end of chlorin chromophore. The syntheses of 9 unreported chlorins related to chlorophyll with novel carbon skeleton were accomplished and their chemical structures were characterized by elemental analysis, UV, IR and 1H NMR spectra.

Key words: chlorophyll-a, pyropheophorbide, chlorin, chemical reaction, synthesis