1-[4-(3-chloro-3-fluoropropyl)piperazin-1-yl]ethanone | 1265340-76-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 1-[4-(3-chloro-3-fluoropropyl)piperazin-1-yl]ethanone
• 英文别名: 1-(4-(3-chloro-3-fluoropropyl)piperazin-1-yl)ethan-1-one
• CAS: 1265340-76-8
• 化学式: C₉H₁₆ClFN₂O
• 分子量: 222.69
• InChiKey: CMPOIKJKVWGRHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-(4-(3-chloroallyl)piperazin-1-yl)ethan-1-one 在 氢氟酸 、 五氟化锑 作用下， 反应 0.02h， 以60%的产率得到1-[4-(3-chloro-3-fluoropropyl)piperazin-1-yl]ethanone
  参考文献：
  名称：

  Selective Synthesis of gem-Chlorofluorinated Nitrogen-Containing Derivatives after Superelectrophilic Activation in Superacid HF/SbF₅

  摘要：

  The first direct selective synthesis of novel gem-chloro-fluorinated nitrogen-containing building blocks in super-acid is reported. The dramatic role of the chlorine atom on the reaction is shown by in situ NMR experiments and allows the involvement of a novel original superelectrophilic activation process in superacid HF/SbF5 to be postulated.

  DOI：

  10.1021/jo102225w

文献信息

• Tandem superelectrophilic activation for the regioselective chlorofluorination of recalcitrant allylic amines
  作者：Alexandre Le Darz、Ugo Castelli、Naima Mokhtari、Agnès Martin-Mingot、Jérôme Marrot、Fodil Bouazza、Omar Karam、Sébastien Thibaudeau

  DOI：10.1016/j.tet.2015.12.013

  日期：2016.2

  An efficient and straightforward regio-controlled route to beta-fluoro-gamma-chlorinated amines was developed via an ammonium-chloronium superelectrophilic activation in superacid HF/SbF5. Through halogen directing effect the method was extended to a variety of (poly)halofluorinated building blocks amenable for further synthetic modifications. The direct synthesis of chlorofluorinated analogues of bioactive compounds via this process confirmed the ability to use this strategy for further applications in medicinal chemistry. (C) 2015 Elsevier Ltd. All rights reserved.
• WO2024074501A1
  申请人：——

  公开号：——

  公开（公告）日：——
• Selective Synthesis of <i>gem</i>-Chlorofluorinated Nitrogen-Containing Derivatives after Superelectrophilic Activation in Superacid HF/SbF₅
  作者：Fei Liu、Agnès Martin-Mingot、Marie-Paule Jouannetaud、Christian Bachmann、Gilles Frapper、Fabien Zunino、Sébastien Thibaudeau

  DOI：10.1021/jo102225w

  日期：2011.3.4

  The first direct selective synthesis of novel gem-chloro-fluorinated nitrogen-containing building blocks in super-acid is reported. The dramatic role of the chlorine atom on the reaction is shown by in situ NMR experiments and allows the involvement of a novel original superelectrophilic activation process in superacid HF/SbF5 to be postulated.