焦脱镁叶绿酸-a甲酯的20-meso-位氯代反应及其光谱性质  

Chlorination of Pyropheophorbide-a at 20-meso-Position and Their Spectral Propcrties

作　　者：杨泽[1] 王振[2] 刘洋[1] 徐希森[1] 王进军[1,2] 

机构地区：[1]烟台大学化学化工学院,山东烟台264005 [2]烟台大学药学院,山东烟台264005

出　　处：《烟台大学学报（自然科学与工程版）》2012年第3期174-179,共6页Journal of Yantai University(Natural Science and Engineering Edition)

基　　金：国家科技部中匈政府间合作项目(2008年);山东省自然科学基金资助项目(Y2008B49)

摘　　要：以叶绿素-a为起始原料,通过在乙酸中回流和在甲醇中甲基化,一步完成剔除金属镁离子和脱去132-位甲氧甲酰基,以49%的收率完成焦脱镁叶绿酸-a甲酯1的合成.选择过氧化氢/氯化氢或者N-氯代丁二酰亚胺(NCS)为氯化剂,对其20-meso-位进行氯代,分别以72%和82%的产率得到20-氯焦脱镁叶绿酸-a甲酯2.对氯代反应的反应机理进行讨论的同时,对氯代前后叶绿素类二氢卟吩的紫外-可见光谱和核磁共振光谱进行表征、归属和比对,解释和总结了导致变化的相应原因和机理.Methyl pyropheophorbide-a 1 is obtained with 49% yield from chlorophyll-a. The process includes removing central magnesium ion and C132-carbomethoxyl group in one-pot method by reflux in acetic acid and methylation in methanol. The chlorination at 20-meso-position of methyl pyropheo-phorbide-a is carried out using hydrogen peroxide/hydrogen chloride or N-chlorosuccinimide （NCS） as chlorinating agent to generate methyl 20-chloropyropheophorbide-a in 72% and 82% yield, respectively. As the reaction mechanisms are discussed, the Uv-vis and 1H NMR spectra of chlorophyllous chlorins before and after chlorination are characterized, ascribed and compared. The reasons for structural changes due to chlorination are explained and summarized.

关 键 词：叶绿素-A 焦脱镁叶绿酸-a甲酯 氯代反应 紫外-可见光谱 核磁共振光谱 

分 类 号：O644.1[理学—物理化学]