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 Hydroborationoxidation

摘要:

以氯化血红素(1)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，4)。在合成原卟啉二甲酯(3)的过程中，采用了超声激励绿色合成法，并且对反应条件进行了优化，收率达到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的优化。通过1H NMR、MS、UV-vis和IR测试技术对产物结构进行了表征。

Abstract:

[2,7,12,18-tetramethyl-3,8-bis(-2-hydroxy ethyl)-13,17-methoxy carb- onyl ethyl]-porphyrin was prepared from hemin by a three-steps reaction including demetalation, esterification, anti-Markovnikov addition. In the synthesis process of protoporphyrin dimethyl ester, environmental friendly ultrasound method was put to use with the yield of 91.6%. [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 with 1HNMR, MS, UV-vis and IR.