[2,7,12,18-四甲基-3,8-二(1-羟基乙基)-13,17-二羧基乙基]-卟啉的改进合成  

A Modified Synthesis of [2,7,12,18-Tetramethyl-3,8-bis(1-hydroxy ethyl)-13,17-dicarboxy ethyl]-porphyrin

作　　者：徐士超[1] 胡炳成[1] 崔巧利[1] 邓全知[1] 周维友[1] 刘祖亮[1] 

机构地区：[1]南京理工大学化工学院,江苏南京210094

出　　处：《精细化工》2011年第2期205-208,共4页Fine Chemicals

基　　金：江苏省自然科学基金(BK2009386);南京理工大学科技发展基金(2010GJPY043)~~

摘　　要：在酸性条件下,氯化血红素(Ⅰ)与还原性铁粉作用生成原卟啉(Ⅱ),通过HBr-冰醋酸加成不经提纯直接加入NaOH溶液,OH-取代仲位Br制得[2,7,12,18-四甲基-3,8-二(1-羟基乙基)-13,17-二羧基乙基]-卟啉(血卟啉,Ⅲ),反应总产率达到90.6%。探讨了脱铁过程中反应温度、时间、还原剂用量等因素对原卟啉(Ⅱ)合成的影响,反应时间和pH对血卟啉(Ⅲ)合成的影响。结果表明,当氯化血红素和铁粉的摩尔比为1∶1、反应温度为110℃时,原卟啉的产率最高达98.3%;当pH=10,反应时间为6 h时,血卟啉的产率最高达92.1%。通过IR、MS和1HNMR对产物结构进行了表征。Protoporhyrin（Ⅱ） was prepared by the demetalation reaction of hemin using HCOOH-Fe powder.And the target product of[2,7,12,18-tetramethyl-3,8-bis（1-hydroxy ethyl）-13,17-dicarboxy ethyl]-porphyrin（hematoporphyrin） was prepared through the ＂one pot＂ reaction of an HBr-acetic acid addition reaction and an OH-nucleophilic substitution reaction from protoporphyrin without purifying the intermediate.The total yield of hematoporphyrin（Ⅲ） is 90.6%.The effects of temperature,time and the dosage of reducing agent to Ⅱ and the effect of pH and time on the yield of Ⅲ were investigated.The results show that the yield of Ⅱ reaches a maximum of 98.3% in the molar ratio of hemin to Fe powder 1∶ 1 and at the the temperature of 110 ℃ and the optimal reaction pH and reaction time are 10 and 6 h respectively with a maximum yield of 92.1% in the synthesis of product Ⅲ.The target products were characterized with FT-IR,ESI-MS and ^1HNMR.

关 键 词：血红素 血卟啉 卟啉衍生物 

分 类 号：O629.9[理学—有机化学]