Cyclopropylation of Chlorophyllous Degradation Products and Synthesis of Chlorin Derivatives

doi:10.6023/cjoc201310002

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (3): 552-560.DOI: 10.6023/cjoc201310002 Previous Articles Next Articles

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叶绿素降解产物的环丙基化及其二氢卟吩衍生物的合成

刘洋^a, 徐希森^a, 李家柱^a, 殷军港^a, 祁彩霞^b, 王进军^a,b

a 烟台大学化学化工学院烟台 264005;
b 山东省黄金工程技术研究中心(工业应用) 烟台 264005

收稿日期:2013-10-06 修回日期:2013-11-08 发布日期:2013-11-20
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.

Cyclopropylation of Chlorophyllous Degradation Products and Synthesis of Chlorin Derivatives

Liu Yang^a, Xu Xisen^a, Li Jiazhu^a, Yin Jungang^a, Qi Caixia^b, Wang Jinjun^a,b

a College of Chemistry and Chemical Engineering, Yantai University, Yantai 264005;
b Shandong Applied Research Centre of Gold Nanotechnology (Au-SDARC), Yantai 264005

Received:2013-10-06 Revised:2013-11-08 Published:2013-11-20
Supported by:
Project supported by the National Natural Science Foundations of China (No. 21272048) and the Project of Shandong Applied Reaearch Centre of Gold Nanotechnology (2011).

Pheophorbide-a methyl ester, as a degraded product from chlorophyll-a, was used as a starting material, and the modifications for functional groups along N²¹-N²³-axis were completed by making use of reactive regions. The tri-membered ring structures were introduced to the macrocyclic chromophore in different position by 1,3-polar cycloaddition, Grignard reaction and reconstructions for exocyclic ring. A series of unreported chlorins related to chlorophyll were synthesized and their chemical structures were characterized by UV, IR, ¹H NMR, MS techniques and elemental analysis. The different effects on the physical and chemical properties of chlorophyllous chlorins by introduction of cyclopropyl group were discussed and in vitro photodynamic activities of some new compounds were determined.

Key words: chlorophyll-a, chlorin, chemical modification, cyclopropylation, synthesis

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Liu Yang, Xu Xisen, Li Jiazhu, Yin Jungang, Qi Caixia, Wang Jinjun. Cyclopropylation of Chlorophyllous Degradation Products and Synthesis of Chlorin Derivatives[J]. Chin. J. Org. Chem., 2014, 34(3): 552-560.

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叶绿素降解产物的环丙基化及其二氢卟吩衍生物的合成

Cyclopropylation of Chlorophyllous Degradation Products and Synthesis of Chlorin Derivatives

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