叶绿素-a降解产物的硝酸铊氧化反应及其二氢卟吩衍生物的合成
收稿日期: 2015-01-21
修回日期: 2015-03-22
网络出版日期: 2015-04-13
基金资助
国家自然科学基金(No. 21272048)和山东省黄金工程技术研究中心(2011年度)资助项目.
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).
高娜 , 张善国 , 王振 , 王进军 . 叶绿素-a降解产物的硝酸铊氧化反应及其二氢卟吩衍生物的合成[J]. 有机化学, 2015 , 35(8) : 1715 -1725 . DOI: 10.6023/cjoc201501028
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
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