红紫素-18酰亚胺衍生物的合成及其可见光谱的研究

选择脱镁叶绿酸 a甲酯为原料进行 3 位化学修饰和E环改造 .经 3 乙烯基的溴化氢加成和与联苯酚的亲核取代反应 ,完成了 3 位联苯氧基的引入 ;在碱性条件下 ,通过空气氧化将E环转变为环己二羧酸酐形成红紫素 18甲酯衍生物 ;所得氧化产物进而和盐酸羟胺反应 ,经胺解开环和再缩合成环构成N 羟基红紫素 18酰亚胺衍生物 ;对其羟基进行烷基化和酰基化 ,合成出N 取代红紫素 18酰亚胺衍生物 .同时讨论了化学结构变化对分子可见光谱的影响 .所合成新化合物的结构均经UV ,IR ,1 HNMR光谱和元素分析予以确认

Synthesis of Derivatives of Purpurin-18 Imide and Research on the Visible Spectra

Methyl pheophorbide a was used as a starting material for modifications at 3 position and transformation on E ring. The introduction of biphenylyloxy was performed by addition of HBr and nucleophilic substitution with phenylphenol on vinyl group at 3 position. In basic condition E ring was converted into the cyclohexanedicarboxylic anhydride to form purpurin 18 derivatives by the air oxidation. The oxidized products were reacted with hydroxylamine hydrochloride to generate purpurin 18 imide by ammonolysis and recondensation. The alkylation and acylation for hydroxyl group linked with nitrogen were accomplished to give N alkoxy and N acyloxy purpurin 18 imides, respectively. The effect on their visible spectra by variation of chemical construction was discussed. The structures of all new compounds were characterized by elemental analysis, UV, IR and 1H NMR spectra.