Synthesis of 20-meso-Substituted Chlorins with the Basic Skeleton of Chlorophyll-a

doi:10.6023/cjoc1201202

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (11): 2154-2161.DOI: 10.6023/cjoc1201202 Previous Articles Next Articles

Notes

具有叶绿素-a基本骨架的20-meso-位取代二氢卟吩衍生物的合成

王鲁敏^a, 王振^a, 杨泽^a, 金英学^b, 王进军^a,c

a 烟台大学化学化工学院烟台 264005;
b 哈尔滨师范大学化学化工学院哈尔滨 150025;
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:2012-01-20 修回日期:2012-07-12 发布日期:2012-07-18
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. 20972036)和山东省自然科学基金(No. Y2008B49)资助项目.

Synthesis of 20-meso-Substituted Chlorins with the Basic Skeleton of Chlorophyll-a

Wang Lumin^a, Wang Zhen^a, Yang Ze^a, Jin Yingxue^b, Wang Jinjun^a,c

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

Received:2012-01-20 Revised:2012-07-12 Published:2012-07-18
Supported by:
Project supported by the National Natural Science Foundations of China (No. 20972036) and the Natural Science Foundation of Shandong Province of China (No. Y2008B49).

Methyl pheophorbide-a (MPa) was used as starting material. The coupling reaction of MPa with diazobenzene hydrochloride, hydrobromide and sulfate was carried out to give traces of expected product, while major products were 20-halogenated and nitroso-substituted chlorins. Zinc methyl pyropheophorbide-a reacted with 3-N,N-dimethylacrolein to give Vilsmeier product. The bromination of pyropheophorbide-d with N-bromosuccinimide (NBS) formed single 20-brominated product, the vinyl group of which was resumed by Wittig reaction to give 20-bromopyropheophorbide-a. The electrophilic substitution of other chlorphyllous degradation products afforded corresponding 20-meso-substituted chlorin derivatives in better yields, respectively. The structures of all the new chlorins with basic skeleton of chlorophyll were characterized by UV, IR, ¹H NMR spectra and elemental analysis.

Key words: chlorophyll-a, pheophorbide-a, pyropheophorbide-a, chlorin, electrophilic reaction

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Wang Lumin, Wang Zhen, Yang Ze, Jin Yingxue, Wang Jinjun. Synthesis of 20-meso-Substituted Chlorins with the Basic Skeleton of Chlorophyll-a[J]. Chin. J. Org. Chem., 2012, 32(11): 2154-2161.

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具有叶绿素-a基本骨架的20-meso-位取代二氢卟吩衍生物的合成

Synthesis of 20-meso-Substituted Chlorins with the Basic Skeleton of Chlorophyll-a

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