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Citation: XU Shichao, HU Bingcheng, CUI Qiaoli, ZHOU Weiyou, LUO Haitao, LIU Zuliang. Synthesis of 3,8-Bisacetyl Deuteroporphyrin Dimethyl Ester[J]. Chinese Journal of Applied Chemistry, ;2011, 28(6): 657-661. doi: 10.3724/SP.J.1095.2011.00459 shu

Synthesis of 3,8-Bisacetyl Deuteroporphyrin Dimethyl Ester

1.
College of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094

Corresponding author: HU Bingcheng,
Received Date: 5 August 2010
Available Online: 29 September 2010
Fund Project: 江苏省自然科学基金(BK2009386) (BK2009386)南京理工大学科技发展基金(2010GJPY043)资助项目 (2010GJPY043)

3,8-Bis-(1-hydroxyethyl) deuteroporphyrin dimethyl ester(Ⅲ) was prepared from hemin(I) by the ways of HBr-H₃CCOOH addition reaction,OH^- nucleophilic substitution reaction and anhydrous hydrogen chloride catalyzed esterification.It was then oxidized by Jones reagent to form 3,8-bisacetyl deuteroporphyrin dimethyl ester(Ⅳ).The effects of reaction temperature and reaction time on the yield of 3,8-bis-(1-hydroxyethyl) deuteroporphyrin dimethyl ester(Ⅱ) were studied.The conditions of esterification reaction were modified.A cheaper and selective oxidant was used in the synthesization of 3,8-bisacetyl deuteroporphyrin dimethyl ester(Ⅳ).The results showed that the yield of hematoporphyrin(Ⅱ) reaches to the highest of 98.5% when the temperature is 35℃ and the reaction time is 25 h.The yield of hematoporphyrin dimethyl ester is 72.1% when the catalyst is anhydrous hydrogen chloride.The cost of 3,8-bisacetyl deuteroporphyrin dimethyl ester(Ⅳ) was decreased greatly when the oxidant is Jones reagent.The target products were characterized with ¹H NMR,IR and MS.
- hemin,
- hematoporphyrin,
- porphyrin derivatives,
- synthesis
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