Nitration (Nitroalkylation) of Pheophorbide and Synthesis of Chlorophyllous Chlorin Derivatives

doi:10.6023/cjoc202004054

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (9): 2895-2903.DOI: 10.6023/cjoc202004054 Previous Articles Next Articles

脱镁叶绿酸的硝(烃基)化反应及其叶绿素类二氢卟吩衍生物的合成

张珠^a, 李家柱^b, 王欣悦^b, 马计划^b, 王旭^b, 王进军^a,b

a 烟台大学文经学院食品与生物工程系山东烟台 264005;
b 烟台大学化学化工学院山东烟台 264005

收稿日期:2020-04-30 修回日期:2020-05-31 发布日期:2020-06-13
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）和山东省自然科学基金（No.ZR2015BQ012）资助项目.

Nitration (Nitroalkylation) of Pheophorbide and Synthesis of Chlorophyllous Chlorin Derivatives

Zhang Zhu^a, Li Jiazhu^b, Wang Xinyue^b, Ma Jihua^b, Wang Xu^b, Wang Jinjun^a,b

a Department of Food & Biological Engineering, Wenjing College, Yantai University, Yantai, Shandong 264005;
b College of chemistry and chemical engineering, Yantai University, Yantai, Shandong 264005

Received:2020-04-30 Revised:2020-05-31 Published:2020-06-13
Supported by:
Project supported by the National Natural Science Foundations of China (No. 21272048) and the Natural Science Foundation of Shandong Province (No. ZR2015BQ012).

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Abstract

Pyropheophorbide-a methyl ester was used as a starting material, and the chemical modification was carried out making use of its active groups attached to the chlorin periphery to establish the formyl group, ketene and α-diketone moieties around the N²¹-N²³ axis. The nitrations or nitroalkylations at 3-, 12-, 20-position and on the exocyclic ring were performed by the electrophilic substitution on the aromatic macrocyclic chromophore, Henry reaction at the active carbonyl groups, and Michael addition to the β-keto ester and the ketene structures on the exocyclic ring as different donor-acceptor. A series of unreported nitro(nitroalkyl) substituted chlorins related to chlorophyll were synthesized and their chemical structures were characterized by elemental analysis, UV-Vis, IR and ¹H NMR spectra.

Key words: chlorophyll, pheophorbide, chlorin, nitration(nitroalkylation) reaction, synthesis

Cite this article

Zhang Zhu, Li Jiazhu, Wang Xinyue, Ma Jihua, Wang Xu, Wang Jinjun. Nitration (Nitroalkylation) of Pheophorbide and Synthesis of Chlorophyllous Chlorin Derivatives[J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2895-2903.

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脱镁叶绿酸的硝(烃基)化反应及其叶绿素类二氢卟吩衍生物的合成

Nitration (Nitroalkylation) of Pheophorbide and Synthesis of Chlorophyllous Chlorin Derivatives

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