N-benzoyl-3-trifluoromethyl-2,5-dihydropyrrole

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-benzoyl-3-trifluoromethyl-2,5-dihydropyrrole
• 英文别名: Phenyl-[3-(trifluoromethyl)-2,5-dihydropyrrol-1-yl]methanone
• 化学式: C₁₂H₁₀F₃NO
• 分子量: 241.213
• InChiKey: IAVWKRSDLDVWCL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-丙-2-烯基苯甲酰胺 在 Grubbs catalyst first generation 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 N-benzoyl-3-trifluoromethyl-2,5-dihydropyrrole
  参考文献：
  名称：

  Fluorinated (hetero)cycles via ring-closing metathesis of fluoride- and trifluoromethyl-functionalized olefins

  摘要：

  Ring-closing metathesis(RCM) has been shown to be a viable tool to incorporate fluoride and trifluoromethyl substituents in (hetero)cyclic ring systems. 2-Fluoroacrylamides were cyclized to the corresponding lactams, and trifluoromethyl- substituted olefins were cyclized to yield trifluoromethylated cyclopentenes, pyrrolines and a dihydrofuran derivative. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.11.093

文献信息

• RCM-Mediated Synthesis of Trifluoromethyl-Containing Nitrogen Heterocycles
  作者：Valeria De Matteis、Floris L. van Delft、Harald Jakobi、Stephen Lindell、Jörg Tiebes、Floris P. J. T. Rutjes

  DOI：10.1021/jo060893z

  日期：2006.9.1

  A ring-closing metathesis mediated pathway to trifluoromethyl-containing piperidines is detailed. This involves the development of a synthetic route to a new (trifluoromethyl)allylating reagent via a Diels-Alder/retro-Diels-Alder strategy, its application in the synthesis of a series of trifluormethyl-substituted diolefin precursors for ring-closing metathesis, and eventually the successful cyclization of these precursor molecules into the corresponding functionalized piperidines.