Oxidation Reactions of Chlorophyll Degradation Products with Thallum Nitrate and Synthesis of Chlorophyllous Chlorins Derivatives

doi:10.6023/cjoc201501028

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (8): 1715-1725.DOI: 10.6023/cjoc201501028 Previous Articles Next Articles

ARTICLE

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

高娜^a, 张善国^b, 王振^b, 王进军^a,b

a 烟台大学文经学院食品与生物工程系烟台 264005;
b 烟台大学化学化工学院烟台 264005

收稿日期:2015-01-21 修回日期:2015-03-22 发布日期:2015-04-13
通讯作者: 王进军 E-mail:wjj1955@163.com
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

Gao Na^a, Zhang Shanguo^b, Wang Zhen^b, Wang Jinjun^a,b

a Department of Food & Biological Engineering, Wenjing College, Yantai University, Yantai 264005;
b College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005

Received:2015-01-21 Revised:2015-03-22 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).

1. Oxidation Reactions of Chlorophyll Degradation Products with Thallum Nitrate and Synthesis of Chlorophyllous Chlorins Derivatives.PDF(1550KB)

Abstract

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

Cite this article

Gao Na, Zhang Shanguo, Wang Zhen, Wang Jinjun. Oxidation Reactions of Chlorophyll Degradation Products with Thallum Nitrate and Synthesis of Chlorophyllous Chlorins Derivatives[J]. Chin. J. Org. Chem., 2015, 35(8): 1715-1725.

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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

Oxidation Reactions of Chlorophyll Degradation Products with Thallum Nitrate and Synthesis of Chlorophyllous Chlorins Derivatives

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