2-trifluoromethylbicyclo[2.2.1]hept-5-ene-2-methanol | 693826-78-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-trifluoromethylbicyclo[2.2.1]hept-5-ene-2-methanol
• 英文别名: [2-(Trifluoromethyl)-2-bicyclo[2.2.1]hept-5-enyl]methanol
• CAS: 693826-78-7
• 化学式: C₉H₁₁F₃O
• 分子量: 192.181
• InChiKey: BOHQOURMRIEKLE-UHFFFAOYSA-N

物化性质

• 熔点：
  52.7 °C
• 沸点：
  186.7±35.0 °C(Predicted)
• 密度：
  1.293±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  对甲苯磺酰氯 、 2-trifluoromethylbicyclo[2.2.1]hept-5-ene-2-methanol 在 吡啶 作用下， 反应 24.0h， 以92%的产率得到toluene-4-sulfonic acid 2-trifluoromethylbicyclo[2.2.1]hept-5-ene-2-methyl 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
• 作为产物：
  描述：

  2-trifluoromethylbicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 5.0h， 以82%的产率得到2-trifluoromethylbicyclo[2.2.1]hept-5-ene-2-methanol
  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.