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


张珠a, 李家柱b, 王欣悦b, 马计划b, 王旭b, 王进军a,b   

  1. 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
  • 基金资助:

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

Zhang Zhua, Li Jiazhub, Wang Xinyueb, Ma Jihuab, Wang Xub, Wang Jinjuna,b   

  1. 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).

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