(2S)-1,1,1-trifluoro-3-[methyl-[[(1R,2R)-2-phenylcyclopropyl]methyl]amino]propan-2-ol | 902757-57-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2S)-1,1,1-trifluoro-3-[methyl-[[(1R,2R)-2-phenylcyclopropyl]methyl]amino]propan-2-ol
• CAS: 902757-57-7
• 化学式: C₁₄H₁₈F₃NO
• 分子量: 273.298
• InChiKey: ZBNXMPOTIIWTOU-AVGNSLFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S)-1,1,1-trifluoro-3-[methyl-[[(1R,2R)-2-phenylcyclopropyl]methyl]amino]propan-2-ol 在 18-冠醚-6 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 24.0h， 生成 2-phenyl-1-(N,N-dimethylamino)methyl-cyclopropane
  参考文献：
  名称：

  Trifluoromethylated amino alcohol as chiral auxiliary for highly diastereoselective and fast Simmons–Smith cyclopropanation of allylic amine

  摘要：

  Three advantages of a trifluoromethylated amino alcohol auxiliary in the Simmons-Smith cyclopropanation of allylic amines are described. The trifluoromethylated amino alcohol auxiliary reduces unwanted side reactions induced by its acidic, and thus less nucleophilic, hydroxy group. The auxiliary accelerated the reaction rate by its electron-withdrawing effect, and promoted the reaction with excellent diastereoselectivity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.04.031
• 作为产物：
  描述：

  N-甲基肉桂基胺 以 二氯甲烷 、 乙腈 为溶剂， 反应 25.0h， 生成 (2S)-1,1,1-trifluoro-3-[methyl-[[(1R,2R)-2-phenylcyclopropyl]methyl]amino]propan-2-ol
  参考文献：
  名称：

  Trifluoromethylated amino alcohol as chiral auxiliary for highly diastereoselective and fast Simmons–Smith cyclopropanation of allylic amine

  摘要：

  Three advantages of a trifluoromethylated amino alcohol auxiliary in the Simmons-Smith cyclopropanation of allylic amines are described. The trifluoromethylated amino alcohol auxiliary reduces unwanted side reactions induced by its acidic, and thus less nucleophilic, hydroxy group. The auxiliary accelerated the reaction rate by its electron-withdrawing effect, and promoted the reaction with excellent diastereoselectivity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.04.031

文献信息

• Trifluoromethylated amino alcohol as chiral auxiliary for highly diastereoselective and fast Simmons–Smith cyclopropanation of allylic amine
  作者：Toshimasa Katagiri、Naomi Iguchi、Tomomi Kawate、Satoshi Takahashi、Kenji Uneyama

  DOI：10.1016/j.tetasy.2006.04.031

  日期：2006.4

  Three advantages of a trifluoromethylated amino alcohol auxiliary in the Simmons-Smith cyclopropanation of allylic amines are described. The trifluoromethylated amino alcohol auxiliary reduces unwanted side reactions induced by its acidic, and thus less nucleophilic, hydroxy group. The auxiliary accelerated the reaction rate by its electron-withdrawing effect, and promoted the reaction with excellent diastereoselectivity. (c) 2006 Elsevier Ltd. All rights reserved.