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| 焦脱镁叶绿酸-a甲酯的20-meso-位氯代反应及其光谱性质 | |
| 引用本文： | 杨泽,王振,刘洋,徐希森,王进军.焦脱镁叶绿酸-a甲酯的20-meso-位氯代反应及其光谱性质[J].烟台大学学报(自然科学与工程版),2012,25(3):174-179. |
| 作者姓名： | 杨泽 王振 刘洋 徐希森 王进军 |
| 作者单位： | 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 3. 烟台大学化学化工学院,山东烟台264005;烟台大学药学院,山东烟台264005 |
| 基金项目： | 国家科技部中匈政府间合作项目，山东省自然科学基金资助项目 |
| 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13^2-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Ⅳ-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一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． |
| 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 |
Chlorination of Pyropheophorbide-a at 20-meso-Position and Their Spectral Propcrties |
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| YANG Ze , WANG Zhen , LIU Yang , XU Xi-sen , WANG Jin-jun.Chlorination of Pyropheophorbide-a at 20-meso-Position and Their Spectral Propcrties[J].Journal of Yantai University(Natural Science and Engineering edirion),2012,25(3):174-179. | |
| Authors: | YANG Ze WANG Zhen LIU Yang XU Xi-sen WANG Jin-jun |
| Institution: | 1,2(1.School of Chemistry and Chemical Engineering,Yantai University,Yantai 264005,China;2.School of Pharmacy,Yantai University,Yantai 264005,China) |
| Abstract: | 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. |
| Keywords: | chlorophyll-a methyl pyropheophorbide-a chlorination reaction ultraviolet-visible spectrophotome-try nuclear magnetic resonance spectroscopy |
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