<(1R-2R)-(2-trifluoromethyl-1-phenyl)cyclopropyl>methylamine | 248601-43-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: <(1R-2R)-(2-trifluoromethyl-1-phenyl)cyclopropyl>methylamine
• 英文别名: [(1R,2S)-1-phenyl-2-(trifluoromethyl)cyclopropyl]methanamine
• CAS: 248601-43-6
• 化学式: C₁₁H₁₂F₃N
• 分子量: 215.218
• InChiKey: GGIGCBFURJWXDF-UWVGGRQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.47
• 重原子数：
  15.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  26.02
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (R)-(+)-2-溴丙酸 、 <(1R-2R)-(2-trifluoromethyl-1-phenyl)cyclopropyl>methylamine 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以7%的产率得到N-<(1R,2S)-(2-trifluoromethyl-1-phenyl)cyclopropyl>methyl-(R)-2-bromo-propionamide
  参考文献：
  名称：

  Intramolecular SN2 reaction α- to a trifluoromethyl group: preparation of 1-cyano-2-trifluoromethylcyclopropane

  摘要：

  The first intramolecular S(N)2 reaction of alpha-trifluoromethylated secondary alcohols by a carbanion is described. A stereoselective intramolecular cyclization of 3-substituted-3-cyano-1-trifluoromethylpropyl sulfonate via the cyano stabilized carbanion provides 1-substituted-1-cyano-2-trifluoromethylcyclopropanes in good yields. The product has the opposite configuration to the starting alcohol at the carbon attached to trifluoromethyl group, revealing the reaction takes place in S(N)2 manner with Walden inversion at the reaction center. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00253-0
• 作为产物：
  描述：

  (S)-5,5,5-Trifluoro-4-hydroxy-2-phenyl-pentanenitrile 在 lithium aluminium tetrahydride 、 sodium hydride 、 对甲苯磺酰氯 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.0h， 生成 <(1R-2R)-(2-trifluoromethyl-1-phenyl)cyclopropyl>methylamine
  参考文献：
  名称：

  Intramolecular SN2 reaction α- to a trifluoromethyl group: preparation of 1-cyano-2-trifluoromethylcyclopropane

  摘要：

  The first intramolecular S(N)2 reaction of alpha-trifluoromethylated secondary alcohols by a carbanion is described. A stereoselective intramolecular cyclization of 3-substituted-3-cyano-1-trifluoromethylpropyl sulfonate via the cyano stabilized carbanion provides 1-substituted-1-cyano-2-trifluoromethylcyclopropanes in good yields. The product has the opposite configuration to the starting alcohol at the carbon attached to trifluoromethyl group, revealing the reaction takes place in S(N)2 manner with Walden inversion at the reaction center. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00253-0

文献信息

• Intramolecular SN2 reaction α- to a trifluoromethyl group: preparation of 1-cyano-2-trifluoromethylcyclopropane
  作者：Toshimasa Katagiri、Minoru Irie、Kenji Uneyama

  DOI：10.1016/s0957-4166(99)00253-0

  日期：1999.7

  The first intramolecular S(N)2 reaction of alpha-trifluoromethylated secondary alcohols by a carbanion is described. A stereoselective intramolecular cyclization of 3-substituted-3-cyano-1-trifluoromethylpropyl sulfonate via the cyano stabilized carbanion provides 1-substituted-1-cyano-2-trifluoromethylcyclopropanes in good yields. The product has the opposite configuration to the starting alcohol at the carbon attached to trifluoromethyl group, revealing the reaction takes place in S(N)2 manner with Walden inversion at the reaction center. (C) 1999 Elsevier Science Ltd. All rights reserved.