(1S,2S)-2-fluoro-N-((S)-1-phenylethyl)cyclohexanamine | 1372857-84-5

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代烷
• 英文名称: (1S,2S)-2-fluoro-N-((S)-1-phenylethyl)cyclohexanamine
• 英文别名: (1S,2S)-2-fluoro-N-[(1S)-1-phenylethyl]cyclohexan-1-amine
• CAS: 1372857-84-5
• 化学式: C₁₄H₂₀FN
• 分子量: 221.318
• InChiKey: JOLVBTIIXWYRQW-UBHSHLNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  二碳酸二叔丁酯 、 (1S,2S)-2-fluoro-N-((S)-1-phenylethyl)cyclohexanamine 在 乙醇 、 20 % Pd(OH)2/C 作用下， 20.0 ℃ 、101.33 kPa 条件下， 反应 8.0h， 以98%的产率得到tert-butyl ((1S,2S)-2-fluorocyclohexyl)carbamate
  参考文献：
  名称：

  Synthesis of β-Fluoroamines by Lewis Base Catalyzed Hydrofluorination of Aziridines

  摘要：

  Lewis base catalysis promotes the in situ generation of amine-HF reagents from benzoyl fluoride and a non-nucleophilic alcohol. The hydrofluorination of aziridines to provide beta-fluoroamines using this latent HF source is described. This protocol displays a broad scope with respect to aziridine substitution and N-protecting groups. Examples of regio- and diastereoselective ring opening to access medicinally relevant beta-fluoroamine building blocks are presented.

  DOI：

  10.1021/jo300433a
• 作为产物：
  描述：

  1-<(1S)-α-phenylethyl>-2,3-tetramethylene aziridine 在 六氟异丙醇 、 苯甲酰氟 、 1,5-二氮杂双环[4.3.0]壬-5-烯 作用下， 以 甲基叔丁基醚 为溶剂， 反应 18.0h， 以63%的产率得到(1S,2S)-2-fluoro-N-((S)-1-phenylethyl)cyclohexanamine
  参考文献：
  名称：

  Synthesis of β-Fluoroamines by Lewis Base Catalyzed Hydrofluorination of Aziridines

  摘要：

  Lewis base catalysis promotes the in situ generation of amine-HF reagents from benzoyl fluoride and a non-nucleophilic alcohol. The hydrofluorination of aziridines to provide beta-fluoroamines using this latent HF source is described. This protocol displays a broad scope with respect to aziridine substitution and N-protecting groups. Examples of regio- and diastereoselective ring opening to access medicinally relevant beta-fluoroamine building blocks are presented.

  DOI：

  10.1021/jo300433a

文献信息

• Synthesis of β-Fluoroamines by Lewis Base Catalyzed Hydrofluorination of Aziridines
  作者：Julia A. Kalow、Dana E. Schmitt、Abigail G. Doyle

  DOI：10.1021/jo300433a

  日期：2012.4.20

  Lewis base catalysis promotes the in situ generation of amine-HF reagents from benzoyl fluoride and a non-nucleophilic alcohol. The hydrofluorination of aziridines to provide beta-fluoroamines using this latent HF source is described. This protocol displays a broad scope with respect to aziridine substitution and N-protecting groups. Examples of regio- and diastereoselective ring opening to access medicinally relevant beta-fluoroamine building blocks are presented.