2-trifluoromethylbicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester | 597581-42-5

• 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: 2-trifluoromethylbicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester
• 英文别名: Methyl 2-(trifluoromethyl)bicyclo[2.2.1]hept-5-ene-2-carboxylate
• CAS: 597581-42-5
• 化学式: C₁₀H₁₁F₃O₂
• 分子量: 220.191
• InChiKey: VVXOXOIAKZHMCU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-trifluoromethylbicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester 在 lithium aluminium tetrahydride 作用下， 以 吡啶 、 乙醚 为溶剂， 反应 24.0h， 生成 toluene-4-sulfonic acid 2-trifluoromethylbicyclo[2.2.1]hept-5-ene-2-methyl 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：

  硫酸二甲酯 、 2-trifluoromethylbicyclo[2.2.1]hept-5-ene-2-carboxylic acid 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以99%的产率得到2-trifluoromethylbicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl 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

文献信息

• Boron Tribromide-Assisted Chiral Phosphoric Acid Catalyst for a Highly Enantioselective Diels–Alder Reaction of 1,2-Dihydropyridines
  作者：Manabu Hatano、Yuta Goto、Atsuto Izumiseki、Matsujiro Akakura、Kazuaki Ishihara

  DOI：10.1021/jacs.5b08693

  日期：2015.10.28

  BBr3-chiral phosphoric acid complexes are highly effective and practical Lewis acid-assisted Brønsted acid (LBA) catalysts for promoting the enantioselective Diels-Alder (DA) reaction of α-substituted acroleins and α-CF3 acrylate. In particular, the DA reaction of α-substituted acroleins with 1,2-dihydropyridines gave the corresponding optically active isoquinuclidines with high enantioselectivities

  BBr3-手性磷酸配合物是一种高效实用的路易斯酸辅助布朗斯台德酸 (LBA) 催化剂，用于促进 α-取代丙烯醛和 α-CF3 丙烯酸酯的对映选择性 Diels-Alder (DA) 反应。特别是，α-取代的丙烯醛与 1,2-二氢吡啶的 DA 反应得到了相应的具有高对映选择性的光学活性异奎宁环。此外，还展示了向吲哚生物碱、长春花碱和别花红素的关键中间体的转化。
• 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.
• US7186773B2
  申请人：——

  公开号：US7186773B2

  公开（公告）日：2007-03-06
• 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.