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β-偕二氟氨基酸衍生物及其单氟烯烃化研究

Pallaidum-catalyzed Suzuki Coupling of Difluoroamino Acid Derivatives and Heterocyclic Boronic Acids

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【作者】 刘宇轩刘剑谭靖颖王博唐石

【Author】 LIU Yuxuan;LIU Jian;TANG Jingying;WANG Bo;TANG Shi;College of Chemistry and Chemical Engineering, Jishou University;

【机构】 吉首大学化学化工学院

【摘要】 本文采用自由基交叉偶联法,合成了含有单氟烯烃结构的偕二氟氨基酸衍生物。本合成路线的起始原料是二苄胺和溴乙酸乙酯,经过胺醛缩合反应、亲核加成反应、羟基Appel溴化反应、heck重排、自由基交叉偶联等反应,成功合成了2-(((E)-3-(苯并[d][1,3]二氧代-4-基)-5-((4-溴苯基)(甲基)氨基)-4-氟戊-3-烯-1-基)(苄基)氨基)-3-苯基己酸乙酯。该合成路线的起始原料价廉易得,步骤简便,具有清洁、易操作、条件温和等优点,可为非天然氨基酸的合成提供新思路。

【Abstract】 The synthesis of difluoroamino acid derivatives contained monofluoroolefin structure by free radical cross-coupling method was studied in this paper. The starting materials of this synthetic route were dibenzylamine and ethyl bromoacetate. Ethyl 2-((E)-3-(benzo[d][1,3]dioxo-4-yl)-5-((4-bromophenyl)(methyl)amino)-4-fluoropent-3-en-1-yl)(benzyl) amino)-3-phenylhexanoate was successfully synthesized by five reaction steps of aminoaldehyde condensation reaction, nucleophilic addition reaction, hydroxyl Appel bromination reaction, heck rearrangement and free radical cross-coupling. The starting materials of the synthesis route were cheap and easy to obtain. The synthesis method was simple, clean and easy to operate, and the conditions were mild.

  • 【文献出处】 化工技术与开发 ,Technology & Development of Chemical Industry , 编辑部邮箱 ,2023年07期
  • 【分类号】O623.736
  • 【下载频次】4
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