4-chloro-N-(4-methoxybenzyl)-1,1,1-trifluorobutan-2-amine | 1384849-72-2

• 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: 4-chloro-N-(4-methoxybenzyl)-1,1,1-trifluorobutan-2-amine
• 英文别名: 4-chloro-1,1,1-trifluoro-N-[(4-methoxyphenyl)methyl]butan-2-amine
• CAS: 1384849-72-2
• 化学式: C₁₂H₁₅ClF₃NO
• 分子量: 281.705
• InChiKey: SXADPPPNSZLRFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-chloro-N-(4-methoxybenzyl)-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85%的产率得到1-(4-methoxybenzyl)-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：

  3-(4-methoxybenzyl)amino-4,4,4-trifluorobutan-1-ol 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以50%的产率得到4-chloro-N-(4-methoxybenzyl)-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