Chemical Reactions of 132-Oxo-pyropheophorbide and Synthesis of Chlorophyllous Chlorins Derivatives

doi:10.6023/cjoc201406047

Chin. J. Org. Chem. ›› 2015, Vol. 35 ›› Issue (1): 181-190.DOI: 10.6023/cjoc201406047 Previous Articles Next Articles

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13²-氧代焦脱镁叶绿酸的化学反应及其叶绿素类二氢卟吩衍生物的合成

杨晓英^a, 张善国^b, 张朋^b, 张千^b, 王振^b, 金英学^a, 祁彩霞^c, 王进军^b,c

a 哈尔滨师范大学化学化工学院哈尔滨 150025;
b 烟台大学文经学院烟台 264005;
c 山东省黄金工程技术研究中心(工业应用) 烟台 264005

收稿日期:2014-06-28 修回日期:2014-09-09 发布日期:2015-01-28
通讯作者: 金英学, 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.

Chemical Reactions of 13²-Oxo-pyropheophorbide and Synthesis of Chlorophyllous Chlorins Derivatives

Yang Xiaoying^a, Zhang Shanguo^b, Zhang Peng^b, Zhang Qian^b, Wang Zhen^b, Jin Yingxue^a, Qi Caixia^c, Wang Jinjun^b,c

a College of Chemistry & Chemical Engineering, Harbin Normal University, Harbin 150025;
b Wenjing College, Yantai University, Yantai 264005;
c Shandong Applied Research Centre of Gold Nanotechnology (Au-SDARC), Yantai 264005

Received:2014-06-28 Revised:2014-09-09 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).

1. Chemical Reactions of 13²-Oxo-pyropheophorbide and Synthesis of Chlorophyllous Chlorins Derivatives.PDF(2669KB)

Abstract

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

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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]. Chin. J. Org. Chem., 2015, 35(1): 181-190.

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13²-氧代焦脱镁叶绿酸的化学反应及其叶绿素类二氢卟吩衍生物的合成

Chemical Reactions of 13²-Oxo-pyropheophorbide and Synthesis of Chlorophyllous Chlorins Derivatives

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132-氧代焦脱镁叶绿酸的化学反应及其叶绿素类二氢卟吩衍生物的合成