1-(2-phenylethyl)-2-(trifluoromethyl)azetidine | 1384849-78-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(2-phenylethyl)-2-(trifluoromethyl)azetidine
• CAS: 1384849-78-8
• 化学式: C₁₂H₁₄F₃N
• 分子量: 229.245
• InChiKey: BXZYSVROPJWJNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-phenylethyl)-2-(trifluoromethyl)azetidine 在 氢溴酸 作用下， 以 水 为溶剂， 反应 48.0h， 以66%的产率得到4-bromo-N-phenylethyl-1,1,1-trifluorobutan-2-amine
  参考文献：
  名称：

  Synthesis of 1-Alkyl-2-(trifluoromethyl)azetidines and Their Regiospecific Ring Opening toward Diverse α-(Trifluoromethyl)Amines via Intermediate Azetidinium Salts

  摘要：

  A convenient approach toward nonactivated 1-alkyl-2-(trifluoromethyl)azetidines as a new class of constrained azaheterocycles was developed staffing from ethyl 4,4,4-trifluoroacetoacetate via imination, hydride reduction, chlorination, and base-induced ring closure. Furthermore, the reactivity profile of these 2-CF3-azetidines was assessed by means of quaternization and subsequent regiospecific ring opening at C4 of the azetidinium intermediates by oxygen, nitrogen, carbon, sulfur, and halogen nucleophiles, pointing to a clear difference in reactivity compared to azetidines bearing other types of electron-withdrawing groups at C2.

  DOI：

  10.1021/jo300694y
• 作为产物：
  描述：

  4-chloro-N-(phenylethyl)-1,1,1-trifluorobutan-2-amine 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以81%的产率得到1-(2-phenylethyl)-2-(trifluoromethyl)azetidine
  参考文献：
  名称：

  Synthesis of 1-Alkyl-2-(trifluoromethyl)azetidines and Their Regiospecific Ring Opening toward Diverse α-(Trifluoromethyl)Amines via Intermediate Azetidinium Salts

  摘要：

  A convenient approach toward nonactivated 1-alkyl-2-(trifluoromethyl)azetidines as a new class of constrained azaheterocycles was developed staffing from ethyl 4,4,4-trifluoroacetoacetate via imination, hydride reduction, chlorination, and base-induced ring closure. Furthermore, the reactivity profile of these 2-CF3-azetidines was assessed by means of quaternization and subsequent regiospecific ring opening at C4 of the azetidinium intermediates by oxygen, nitrogen, carbon, sulfur, and halogen nucleophiles, pointing to a clear difference in reactivity compared to azetidines bearing other types of electron-withdrawing groups at C2.

  DOI：

  10.1021/jo300694y