(2R,3S)-3-amino-1,1,1-trifluorobutan-2-ol hydrochloride | 1009606-47-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: (2R,3S)-3-amino-1,1,1-trifluorobutan-2-ol hydrochloride
• 英文别名: (2R,3S)-3-amino-1,1,1-trifluorobutan-2-ol;hydrochloride
• CAS: 1009606-47-6
• 化学式: C₄H₈F₃NO*ClH
• 分子量: 179.57
• InChiKey: VFMKPKXHRNKGGM-LJUKVTEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.68
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  46.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  tert-butyl ((2S,3R,S)-4,4,4-trifluoro-3-hydroxy-2-butanyl)carbamate 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 3.0h， 以93%的产率得到(2R,3S)-3-amino-1,1,1-trifluorobutan-2-ol hydrochloride
  参考文献：
  名称：

  An Efficient Entry to Optically Active anti- and syn-β-Amino-α-trifluoromethyl Alcohols

  摘要：

  The reaction of chiral 5,6-dihydro-2H-1,4-oxazin-2-ones with TMSCF3 in the presence of a suitable activator leads to trifluoromethyl lactols, which can be selectively reduced to anti-beta-amino-alpha-trifluoromethyl alcohols. The corresponding syn diastereoisomers are obtained when the starting imines are reduced and the nitrogen atom is conveniently protected. In addition, a novel rearrangement of the CF3 group in the lactol intermediates has been observed. This represents a formal CF3 addition to the imine function in the starting substrates.

  DOI：

  10.1021/ol702947n

文献信息

• An Efficient Entry to Optically Active <i>anti</i>- and <i>syn</i>-β-Amino-α-trifluoromethyl Alcohols
  作者：Santos Fustero、Laia Albert、José Luis Aceña、Juan F. Sanz-Cervera、Amparo Asensio

  DOI：10.1021/ol702947n

  日期：2008.2.1

  The reaction of chiral 5,6-dihydro-2H-1,4-oxazin-2-ones with TMSCF3 in the presence of a suitable activator leads to trifluoromethyl lactols, which can be selectively reduced to anti-beta-amino-alpha-trifluoromethyl alcohols. The corresponding syn diastereoisomers are obtained when the starting imines are reduced and the nitrogen atom is conveniently protected. In addition, a novel rearrangement of the CF3 group in the lactol intermediates has been observed. This represents a formal CF3 addition to the imine function in the starting substrates.