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Chinese Journal of Organic Chemistry >

2013 , Vol. 33 >Issue 03: 581 - 589

DOI: https://doi.org/10.6023/cjoc201210053

Articles

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

  • Yin Yifan ,
  • Zhang Qian ,
  • Liu Yang ,
  • Xu Xisen ,
  • Qi Caixia ,
  • Wang Jinjun
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  • a College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005;
    b Shandong Applied Research Centre of Gold Nanotechnology (Au-SDARC), Yantai 264005

Received date: 2012-10-31

  Revised date: 2012-12-01

  Online 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).

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Abstract

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

Cite this article

Yin Yifan , Zhang Qian , Liu Yang , Xu Xisen , Qi Caixia , Wang Jinjun . Hydroxy(alky)lation of Chlorophyllous Degradation Products and Synthesis of Their Chlorin Derivatives[J]. Chinese Journal of Organic Chemistry, 2013 , 33(03) : 581 -589 . DOI: 10.6023/cjoc201210053

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