ethyl 3-(phenylethyl)amino-4,4,4-trifluorobut-2-enoate | 1384849-57-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl 3-(phenylethyl)amino-4,4,4-trifluorobut-2-enoate
• 英文别名: ethyl 3-(2-phenylethyl)amino-4,4,4-trifluorobut-2-enoate
• CAS: 1384849-57-3
• 化学式: C₁₄H₁₆F₃NO₂
• 分子量: 287.282
• InChiKey: BZPVZRDZVVUHGH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.83
• 重原子数：
  20.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.33
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl 3-(phenylethyl)amino-4,4,4-trifluorobut-2-enoate 在 sodium tetrahydroborate 、 氯化亚砜 、 乙醇 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 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
• 作为产物：
  描述：

  2-苯乙胺 、 三氟乙酰乙酸乙酯 在 溶剂黄146 作用下， 以 氯仿 为溶剂， 反应 5.08h， 以78%的产率得到ethyl 3-(phenylethyl)amino-4,4,4-trifluorobut-2-enoate
  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