具有芳并咪唑结构单元的叶绿素类二氢卟吩衍生物的合成  

Syntheses of Chlorophyllous Chlorin Derivatives with Aromatic Ring-Fused Imidazole Structural Unit

作　　者：张珠[1] 赵雨 王欣悦 李家柱[2] 王进军[1,2] Zhu Zhang;Yu Zhao;Xinyue Wang;Jiazhu Li;Jinjun Wang(Department of Food&Biological Engineering,Wenjing College,Yantai University,Yantai,Shandong 264005;College of Chemistry and Chemical Engineering,Yantai University,Yantai,Shandong 264005)

机构地区：[1]烟台大学文经学院食品与生物工程系,山东烟台264005 [2]烟台大学化学化工学院,烟台264005

出　　处：《有机化学》2021年第3期1177-1186,共10页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.21272048);山东省自然科学基金(No.ZR2015BQ012)资助项目。

摘　　要：以脱镁叶绿酸-a甲酯为起始原料,利用其外接环的结构转换,在N^(21)-N^(23)轴水溶性端向的不同位置上构建了甲酰基和邻位二酮结构;通过连有活性官能团的叶绿素类二氢卟吩与多种芳香邻位二胺进行类Phillps-Ladenburg反应,以连接和并合的方式在其周环上引进了芳并咪唑结构单元;完成了一系列未见报道的具有芳并咪唑结构单元的叶绿素类二氢卟吩衍生物的合成,讨论了相应的反应机理和咪唑化产物的紫外-可见光谱性质.所有新合成化合物的结构均经UV-Vis、IR、^(1)H NMR、MS及元素分析予以证实.Using pheophorbide-a methyl ester as starting material, the formyl group and α-diketone moiety were introduced into the water-soluble end of N^(21)-N^(23) axis at different positions by the structural transformation on exocyclic ring. Furthermore, using the Phillps-Ladenburg-like reaction of active functional groups in chlorophyll chlorins with various aromatic o-diamines, the aromatic ring-fused imidazole structural units were created in linkage or fused manner, and a series of unreported chlorin derivatives that contain aryl-fused imidazol unit were finally synthesized. Besides, the relevant reaction mechanism was analyzed, and the absorption properties of these imidazolized products were discussed. The chemical structures of all newly synthesized compounds were characterized by elemental analysis, MS, UV-Vis, IR and ^(1)H NMR spectra.

关 键 词：叶绿素 脱镁叶绿酸 二氢卟吩 芳并咪唑化 合成 

分 类 号：O626.23[理学—有机化学]