(R)-2-(N-benzyl-N-methylamino)-3,3,3-trifluoro-1-propanol

• 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: (R)-2-(N-benzyl-N-methylamino)-3,3,3-trifluoro-1-propanol
• 英文别名: (2R)-2-[benzyl(methyl)amino]-3,3,3-trifluoropropan-1-ol
• 化学式: C₁₁H₁₄F₃NO
• 分子量: 233.233
• InChiKey: DVMWBZKYLVFOMK-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  23.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  trimethoxonium tetrafluoroborate 、 N-benzyl-2-trifluoromethylaziridine 在 水 作用下， 以 二氯甲烷 为溶剂， 反应 0.84h， 以82%的产率得到(R)-2-(N-benzyl-N-methylamino)-3,3,3-trifluoro-1-propanol
  参考文献：
  名称：

  General Syntheses of Optically Active α-Trifluoromethylated Amines via Ring-Opening Reactions of N-Benzyl-2-trifluoromethylaziridine

  摘要：

  Syntheses of optically active trifluoromethylated amines via ring-opening reactions of optically active N-benzyl-2-trifluoromethylaziridine were achieved. Proton-catalyzed ring-opening reactions of the 2-trifluoromethylaziridine proceeded very smoothly, while the compound was found to be inert toward nucleophiles; thus, the trifluoromethylaziridine itself cannot be ring-opened by nitrogen or carbon nucleophiles. The N-alkylated aziridinium ion of trifiuoromethylaziridine was highly reactive to undergo smooth ring-opening by nitrogen and carbon nucleophiles.

  DOI：

  10.1021/jo990207e

文献信息

• General Syntheses of Optically Active α-Trifluoromethylated Amines via Ring-Opening Reactions of <i>N</i>-Benzyl-2-trifluoromethylaziridine
  作者：Toshimasa Katagiri、Mikihiro Takahashi、Yasuyuki Fujiwara、Hideki Ihara、Kenji Uneyama

  DOI：10.1021/jo990207e

  日期：1999.10.1

  Syntheses of optically active trifluoromethylated amines via ring-opening reactions of optically active N-benzyl-2-trifluoromethylaziridine were achieved. Proton-catalyzed ring-opening reactions of the 2-trifluoromethylaziridine proceeded very smoothly, while the compound was found to be inert toward nucleophiles; thus, the trifluoromethylaziridine itself cannot be ring-opened by nitrogen or carbon nucleophiles. The N-alkylated aziridinium ion of trifiuoromethylaziridine was highly reactive to undergo smooth ring-opening by nitrogen and carbon nucleophiles.