Chinese Journal of Organic Chemistry >
Acetylation of Chlorophyll-a Degradation Products and Synthesis of Chlorin Derivatives
Received date: 2012-04-03
Revised date: 2012-05-30
Online published: 2012-06-06
Supported by
Project supported by the Project of Technology Cooperation between Covernments of China and Hungary (No. 2008-333-4-32) and the Project of Shandong Applied Research Centre of Gold Nanotechnology (No. 2011).
Methyl pheophorbide-a (MPa) was used as starting material and converted to Ni(II) complexes by modifying for chemical structures and metallizing with Ni(acac)2. Their Vilsmerier reactions with phosphoryl chloride and 3-(dimethyl- amino)-acrolein or N,N-dimethylformamide were performed regioselectively to introduce formyl or formylvinyl group on the periphery of chlorin. The formylmethyl group also was established by oxidation reaction of the C(3)-vinyl group with thallium nitrate. The hydroxyalkyloxyl or hydroxyalkylamino group on the macrocycle was constructed based on the chemical activities of the vinyl group at 3-position and ketone group in E-ring and subsequently the hydroxyl group was oxidized with the conbination of tetrapropylammonium perruthenate (TPAP) and N-methylmorpholine N-oxide to the corresponding formyl group, respectively. The structures of all the new chlorins containing acyl structure were characterized by UV, IR, 1H NMR spectra and elemental analysis.
Key words： chlorophyll-a; pheophorbide-a; chlorin; acetylation reaction
Wang Lumin , Yao Nannan , Yang Ze , Wang Zhen , Shim Yongkey , Wang Jinjun . Acetylation of Chlorophyll-a Degradation Products and Synthesis of Chlorin Derivatives[J]. Chinese Journal of Organic Chemistry, 2012 , 32(10) : 1899 -1907 . DOI: 10.6023/cjoc201204003
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