Chinese Journal of Organic Chemistry >
Chemical Reactions of 132-Oxo-pyropheophorbide and Synthesis of Chlorophyllous Chlorins Derivatives
Received date: 2014-06-28
Revised date: 2014-09-09
Online published: 2015-01-28
Supported by
Project supported by the National Natural Science Foundation of China (No. 21272048) and the Project of Shandong Applied Reaearch Centre of Gold Nanotechnology (2011).
Pyropheophorbide-a methyl ester and its 132-oxoed derivatives were used as starting material, and the oxygen-containing functional groups were established on the chlorin periphery by oxygenation with agent and allomerization. The functional group transformation was carried out by classic reactions including Wittig and Grignard reactions in E-ring, electrophilic substitution at 20-meso-position and 1,3-dipolar cyclocaddition with C(3)-vinyl group. The molecule structure, reactive site and chemical selectivity of 132-oxopyropheophorbide-a were also discussed. The syntheses of a series of unreported chlorins related to chlorophyll were accomplished and their chemical structures were characterized by elemental analysis, UV, IR and 1H NMR spectra.
Key words： chlorophyll-a; chlorin; 132-oxopyropheophorbide-a; chemical reaction; synthesis
Yang Xiaoying , Zhang Shanguo , Zhang Peng , Zhang Qian , Wang Zhen , Jin Yingxue , Qi Caixia , Wang Jinjun . Chemical Reactions of 132-Oxo-pyropheophorbide and Synthesis of Chlorophyllous Chlorins Derivatives[J]. Chinese Journal of Organic Chemistry, 2015 , 35(1) : 181 -190 . DOI: 10.6023/cjoc201406047
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