Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (03): 581-589.DOI: 10.6023/cjoc201210053 Previous Articles     Next Articles



殷一樊a, 张千a, 刘洋a, 徐希森a, 祁彩霞b, 王进军a,b   

  1. a 烟台大学化学化工学院 烟台 264005;
    b 山东省黄金工程技术研究中心(工业应用) 烟台 264005
  • 收稿日期:2012-10-31 修回日期:2012-12-01 发布日期:2012-12-06
  • 通讯作者: 王进军
  • 基金资助:

    国家自然科学基金(No. 21272048 )和山东省自然科学基金(No. Y2008B49)资助项目.

Hydroxy(alky)lation of Chlorophyllous Degradation Products and Synthesis of Their Chlorin Derivatives

Yin Yifana, Zhang Qiana, Liu Yanga, Xu Xisena, Qi Caixiab, Wang Jinjuna,b   

  1. a College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005;
    b Shandong Applied Research Centre of Gold Nanotechnology (Au-SDARC), Yantai 264005
  • Received:2012-10-31 Revised:2012-12-01 Published:2012-12-06
  • Supported by:

    Project supported by the National Natural Science Foundations of China (No. 21272048) and the Natural Science Foundation of Shandong Province (No. Y2008B49).

Methyl pheophorbide-a was used as a starting material, and its modifications were carried out making use of the chemical reactivities of electron-richous regions on the chlorin macrocycle. The introdustions of hydroxyl groups or hydroxyalkyl groups at exocyclic E-ring, C(3)(C12)-β-position and 20-meso-position were accomplished by the allomerizations of α-hydrogen of the exocyclic E-ring, the electrophilic addition of C(3)-vinyl group, the nucleophilic addition of the carbonyl groups and electrophilic substitution at C(20)-position. The newly-formed hydroxyl groups were further converted into carbon-oxygen double bonds or carbon-carbon double bonds by oxidation and dehydration reactions. The chemical structures of 11 unreported chlorin derivatives were characterized by UV, 1H NMR, IR spectra and elemental analysis. The possible mechanisms about corresponding reactions were tentatively proposed.

Key words: chlorophyll-a, pheophorbide, chlorin, hydroxy(alky)lation, synthesis