N-allyl-N-(2-trifluoromethylallyl)carbamic acid tert-butyl ester

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-allyl-N-(2-trifluoromethylallyl)carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-prop-2-enyl-N-[2-(trifluoromethyl)prop-2-enyl]carbamate
• 化学式: C₁₂H₁₈F₃NO₂
• 分子量: 265.276
• InChiKey: LSUCTIUICFQSRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-allyl-N-(2-trifluoromethylallyl)carbamic acid tert-butyl ester 在 Grubbs catalyst first generation 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以97%的产率得到3-trifluoromethyl-2,5-dihydropyrrole-1-carboxylic acid tert-butyl ester
  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
• 作为产物：
  描述：

  叔丁氧基 N-氨基甲酸丙烯 、 2-(trifluoromethyl)allyl 4-methylbenzenesulfonate 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.25h， 以63%的产率得到N-allyl-N-(2-trifluoromethylallyl)carbamic acid tert-butyl ester
  参考文献：
  名称：

  RCM-Mediated Synthesis of Trifluoromethyl-Containing Nitrogen Heterocycles

  摘要：

  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.

  DOI：

  10.1021/jo060893z

文献信息

• Fluorinated (hetero)cycles via ring-closing metathesis of fluoride- and trifluoromethyl-functionalized olefins
  作者：Valeria De Matteis、Floris L. van Delft、René de Gelder、Jörg Tiebes、Floris P.J.T. Rutjes

  DOI：10.1016/j.tetlet.2003.11.093

  日期：2004.1

  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.
• 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.