Acetylation of Chlorophyll-a Degradation Products and Synthesis of Chlorin Derivatives

doi:10.6023/cjoc201204003

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (10): 1899-1907.DOI: 10.6023/cjoc201204003 Previous Articles Next Articles

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叶绿素-a降解产物的酰基化反应及其二氢卟吩衍生物的合成

王鲁敏^a, 姚楠楠^b, 杨泽^a, 王振^a, 沈荣基^c, 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;
c 仁济大学纳米工程学院釜山韩国

收稿日期:2012-04-03 修回日期:2012-05-30 发布日期:2012-06-06
通讯作者: 王进军 E-mail:wjj1955@163.com
基金资助:
中匈政府间科技合作项目(No. 2008-333-4-32 )和山东黄金工程技术研究中心(No. 2011)资助项目.

Acetylation of Chlorophyll-a Degradation Products and Synthesis of Chlorin Derivatives

Wang Lumin^a, Yao Nannan^b, Yang Ze^a, Wang Zhen^a, Shim Yongkey^c, 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;
c School of Nano Engineering, Inji University, Pusan, Korea

Received:2012-04-03 Revised:2012-05-30 Published:2012-06-06
Supported by:
Project supported by the Project of Technology Cooperation between Covernments of China and Hungary (No. 2008-333-4-32) and the Project of Shandong Applied Research Centre of Gold Nanotechnology (No. 2011).

Methyl pheophorbide-a (MPa) was used as starting material and converted to Ni(II) complexes by modifying for chemical structures and metallizing with Ni(acac)₂. Their Vilsmerier reactions with phosphoryl chloride and 3-(dimethyl- amino)-acrolein or N,N-dimethylformamide were performed regioselectively to introduce formyl or formylvinyl group on the periphery of chlorin. The formylmethyl group also was established by oxidation reaction of the C(3)-vinyl group with thallium nitrate. The hydroxyalkyloxyl or hydroxyalkylamino group on the macrocycle was constructed based on the chemical activities of the vinyl group at 3-position and ketone group in E-ring and subsequently the hydroxyl group was oxidized with the conbination of tetrapropylammonium perruthenate (TPAP) and N-methylmorpholine N-oxide to the corresponding formyl group, respectively. The structures of all the new chlorins containing acyl structure were characterized by UV, IR, ¹H NMR spectra and elemental analysis.

Key words: chlorophyll-a, pheophorbide-a, chlorin, acetylation reaction

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Wang Lumin, Yao Nannan, Yang Ze, Wang Zhen, Shim Yongkey, Wang Jinjun. Acetylation of Chlorophyll-a Degradation Products and Synthesis of Chlorin Derivatives[J]. Chin. J. Org. Chem., 2012, 32(10): 1899-1907.

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叶绿素-a降解产物的酰基化反应及其二氢卟吩衍生物的合成

Acetylation of Chlorophyll-a Degradation Products and Synthesis of Chlorin Derivatives

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