Chinese Journal of Organic Chemistry >
Oxidation Reactions of Chlorophyll Degradation Products with Thallum Nitrate and Synthesis of Chlorophyllous Chlorins Derivatives
Received date: 2015-01-21
Revised date: 2015-03-22
Online published: 2015-04-13
Supported by
Project supported by the the national natural Science Foundations of China (No. 21272048) and the Project of Shandong Applied Reaearch Centre of Gold Nanotechnology (2011).
Pyropheophorbide-a methyl ester was used as a starting material, and the chemical modifications and structural transformations along the terminals of N21-N23 axis were carried out by classic chemical reaction, such as electrophilic addition, allomerization, Aldol condensation and ringopening rearrangement, to build new carbon-carbon double bonds on the periphery of the tetrapyrrole macrocycle. Thallum nitrate was chose as oxidizing agent to oxidize the olefinic bonds of different chloropyll degradation products, and Aldol and Friedläender reactions with aromatic aldehydes were performed making use of the chemical activities of the formed formymethyl groups. The synthesis of a series of unreported chlorins related to chlorophyll was accomplished and their chemical structures were characterized by elemental analysis, UV-Vis, IR and 1H NMR spectra.
Key words： chlorophyll-a; chlorin; chemical modification; oxidization reaction; synthesis
Gao Na , Zhang Shanguo , Wang Zhen , Wang Jinjun . Oxidation Reactions of Chlorophyll Degradation Products with Thallum Nitrate and Synthesis of Chlorophyllous Chlorins Derivatives[J]. Chinese Journal of Organic Chemistry, 2015 , 35(8) : 1715 -1725 . DOI: 10.6023/cjoc201501028
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