Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (11): 2279-2287.DOI: 10.6023/cjoc201403067 Previous Articles     Next Articles


杨晓英a, 殷军港b, 金英学a, 祁彩霞c, 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:2014-03-31 修回日期:2014-06-05 发布日期:2014-07-11
  • 通讯作者: 金英学;王进军,
  • 基金资助:


1,3-Dipolar Cycloadditions of (Pyro)pheophorbide-a and Synthesis of Chlorophyllous Chlorin Derivatives

Yang Xiaoyinga, Yin Jungangb, Jin Yingxuea, Qi Caixiac, Wang Jinjunb,c   

  1. 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:2014-03-31 Revised:2014-06-05 Published:2014-07-11
  • 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 (No.2011).

Pheophorbide-a methyl ester was used as a starting material, and new carbon-carbon double bonds were built on the chlorin chromophore by addition, condensation and allomerization. 1,3-Dipolar cycloadditions with different 1,3-dipols for the olefinic bonds at 3-position, 12-position and exocyclic E-ring were performed to synthesize a series of chlorophyllous chlorin derivatives substituted with five-membered heterocycle. The chemical structures of the unreported chlorins were characterized by UV-Vis, 1H NMR, IR, MS and elemental analysis. The region selectivity of 1,3-dipolar cycloadditions and corresponding reaction mechanisms were also discussed.

Key words: chlorophyll-a, chlorin, 1,3-dipolar cycloaddition, region selectivity, synthesis