(R)-1-[(S)-1-phenylethyl]-2-trifluoromethylaziridine | 198019-17-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (R)-1-[(S)-1-phenylethyl]-2-trifluoromethylaziridine
• 英文别名: (2R)-1-[(1S)-1-phenylethyl]-2-(trifluoromethyl)aziridine
• CAS: 198019-17-9
• 化学式: C₁₁H₁₂F₃N
• 分子量: 215.218
• InChiKey: SHWKXNCZSIFMBD-AQZZLOACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-1-[(S)-1-phenylethyl]-2-trifluoromethylaziridine 在 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 反应 48.33h， 生成 (R)-2-((S)-1-phenylethylamino)-3,3,3-trifluoropropyl-4-nitrobenzoate
  参考文献：
  名称：

  Intramolecular SN2 reaction at α-carbon of trifluoromethyl group: preparation of optically active 2-trifluoromethylaziridine

  摘要：

  We have succeeded in intramolecular nucleophilic substitution of the hydroxyl group in (S)-1-(alkylamino)-3,3,3-trifluoro-2-propanol. The reaction provides an optically pure (R)-1-benzyl-2-trifluoromethylaziridine in good yield from optically pure (S)-3-(benzylamino)-1,1,1-trifluoro-2-propanol, which was prepared from (S)-3,3,3-trifluoropropene oxide (75% ee). (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00320-0
• 作为产物：
  描述：

  (S)-1-((S)-1-phenylethylamino)-3,3,3-trifluoro-2-propanol 在 chlorotriphenylphosphonium chloride 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以24%的产率得到(R)-1-[(S)-1-phenylethyl]-2-trifluoromethylaziridine
  参考文献：
  名称：

  Intramolecular SN2 reaction at α-carbon of trifluoromethyl group: preparation of optically active 2-trifluoromethylaziridine

  摘要：

  We have succeeded in intramolecular nucleophilic substitution of the hydroxyl group in (S)-1-(alkylamino)-3,3,3-trifluoro-2-propanol. The reaction provides an optically pure (R)-1-benzyl-2-trifluoromethylaziridine in good yield from optically pure (S)-3-(benzylamino)-1,1,1-trifluoro-2-propanol, which was prepared from (S)-3,3,3-trifluoropropene oxide (75% ee). (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00320-0

文献信息

• Preparation and Reactions of (β-Trifluoromethyl)vinyl Sulfonium Salt
  作者：Ryoko Maeda、Kyoko Ooyama、Ryoko Anno、Masahiro Shiosaki、Takayuki Azema、Takeshi Hanamoto

  DOI：10.1021/ol100768s

  日期：2010.6.4

  (β-Trifluoromethyl)vinyl sulfonium salt as a novel three-carbon fluorinated building block was conveniently prepared from easily available (β-trifluoromethyl)vinyl sulfide and diphenyl iodonium salt in excellent yield. This easily handled crystalline reagent displayed two types of useful transformation involving aziridination and vinylation to afford the corresponding trifluoromethylated compounds in excellent

  （β-三氟甲基）乙烯基sulf盐是新型的三碳氟化结构单元，是由易于获得的（β-三氟甲基）乙烯基硫化物和二苯基碘鎓盐方便地制备的。这种易于处理的结晶试剂显示出两种有用的转化类型，包括叠氮化和乙烯基化，从而以优异的收率提供了相应的三氟甲基化化合物。
• Intramolecular SN2 reaction at α-carbon of trifluoromethyl group: preparation of optically active 2-trifluoromethylaziridine
  作者：Toshimasa Katagiri、Hideki Ihara、Mikihiro Takahashi、Setsuo Kashino、Keizo Furuhashi、Kenji Uneyama

  DOI：10.1016/s0957-4166(97)00320-0

  日期：1997.9

  We have succeeded in intramolecular nucleophilic substitution of the hydroxyl group in (S)-1-(alkylamino)-3,3,3-trifluoro-2-propanol. The reaction provides an optically pure (R)-1-benzyl-2-trifluoromethylaziridine in good yield from optically pure (S)-3-(benzylamino)-1,1,1-trifluoro-2-propanol, which was prepared from (S)-3,3,3-trifluoropropene oxide (75% ee). (C) 1997 Published by Elsevier Science Ltd.