红紫素-18的周环结构修饰及其叶绿素类二氢卟吩衍生物的合成  

Modifications for Peripheral Structures of Purpurin-18 and Synthesis of Chlorophyllous Chlorin Derivatives

作　　者：梁波颖[1] 刘洋[2] 徐希森[2] 金英学[1] 祁彩霞 王进军[2,3] 

机构地区：[1]哈尔滨师范大学化学化工学院,哈尔滨150025 [2]烟台大学化学化工学院,烟台264005 [3]山东省黄金工程技术研究中心(工业应用),烟台264005

出　　处：《有机化学》2013年第11期2357-2366,共10页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(No.21272048);山东省黄金工程技术研究中心(2011年度)资助项目~~

摘　　要：以红紫素-18甲酯为起始原料,利用其3-位乙烯基的多电子性,通过氧化、还原、亲电加成和1,3-偶极环加成等反应,对其N21-N23轴的端向结构进行化学修饰,在周环的3-位上引进了能与大环色基以不同方式形成共轭效应的取代基团,完成了11个未见报道具有红紫素-18碳架的叶绿素类二氢卟吩衍生物的合成,其化学结构均经UV,1H NMR,IR及元素分析予以证实;讨论了红紫素-18的周环结构对其电子光谱所产生的影响,并对相应的化学反应提出了可能的反应机理.Purpurin-18 methyl ester was used as a starting material, and the modifications for the structure on the terminal of its N21-N23-axis were completed making use of electron-richous properties of C（3）-vinyl group by various reactions including oxidation, reduction, electrophilic addition and 1,3-polar cycloaddition. The substituted groups, which could conjugated with macrocyclic chromophore in different form, were introduce to 3-position on the periphery, respectively. The synthesis of 11 unreported chlorophyllous chlorins with basic skeloton of purpurin-18 was accomplished and their chemical structures were characterized by elemental analysis, UV, IR and 1H NMR spectra. The influence of peripheric structure of purpurin-18 on their electronic spectrum was discussed and the possible mechanisms about corresponding reactions were tentatively proposed.

关 键 词：叶绿素-A 二氢卟吩 红紫素-18 化学修饰 合成 

分 类 号：O626[理学—有机化学]