硼氢化-氧化法制备[2,7,12,18-四甲基-3,8-二(2-羟基乙基)-13,17-二甲氧基羰基乙基]-卟啉  

Preparation of [2,7,12,18-Tetramethyl-3,8-bis(2-hydroxy ethyl)-13,17-methoxy carbonyl ethyl]-porphyrin via Hydroboration-oxidation

作　　者：胡田菁[1] 胡炳成[1] 徐士超[1] 黄修友[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》2012年第7期688-691,696,共5页Fine Chemicals

基　　金：江苏省自然科学基金(BK2009386);南京理工大学自主科研专项计划项目(2010GJPY043);江苏省普通高校研究生科研创新基金(CXLX11_0268)~~

摘　　要：以氯化血红素(Ⅰ)为原料,经过脱铁、酯化、反马氏加成得到[2,7,12,18-四甲基-3,8-二(2-羟基乙基)-13,17-二甲氧基羰基乙基]-卟啉(异血卟啉二甲酯,Ⅳ)。在合成原卟啉二甲酯(Ⅲ)的过程中,采用了超声激励法,并且对反应条件进行了优化,产率达到91.6%;然后通过BH3-THF络合物同原卟啉二甲酯3,8-位乙烯基的反马氏加成合成了[2,7,12,18-四甲基-3,8-二(2-羟基乙基)-13,17-二甲氧基羰基乙基]-卟啉,并对加成体系进行适当优化,产率达到64.3%。通过1HNMR、MS、UV-vis和IR测试技术对产物结构进行了表征。[2, 7, 12, 18-Tetramethyl-3,8-bis （2-hydroxy ethyl）-13, 17-methoxy carbonyl ethyl]- porphyrin was prepared from hemin by a three-step reaction including demetalation, esterification, anti- Markovnikov addition. In the synthesis process of protoporphyrin dimethyl ester, environmentally friendly ultrasound method was put to use with the yield of 91.6%. Then, [2,7,12,18-tetramethyl-3, 8-bis （2-hydroxy ethyl）-13, 17-methoxy carbonyl ethyl]-porphyrin was obtained from the anti- Markovnikov addition of protoporphyrin dimethyl ester with BH3-THF with the yield of 64. 3% under reasonably optimized conditions. The target products were characterized by means of ^1 HNMR,MS,UV- vis and IR.

关 键 词：氯化血红素 异血卟啉二甲酯 硼氢化-氧化 医药原料 

分 类 号：O629.9[理学—有机化学]