(R)-2,2,2-trifluoro-1-[(2-methnasulfanyl)phenyl]ethylamine hydrochloride | 842169-98-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: (R)-2,2,2-trifluoro-1-[(2-methnasulfanyl)phenyl]ethylamine hydrochloride
• 英文别名: (R)-2,2,2-trifluoro-1-[(2-methanesulfanyl)phenyl]ethylamine hydrochloride；(1R)-2,2,2-trifluoro-1-(2-methylsulfanylphenyl)ethanamine;hydrochloride
• CAS: 842169-98-6
• 化学式: C₉H₁₀F₃NS*ClH
• 分子量: 257.707
• InChiKey: NSAUZTVFDHUFAD-DDWIOCJRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.39
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  51.3
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-硫代甲基-2,2,2-三氟苯乙酮 在 甲醇 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 (R)-2,2,2-trifluoro-1-[(2-methnasulfanyl)phenyl]ethylamine hydrochloride
  参考文献：
  名称：

  Unprecedented Catalytic Asymmetric Reduction of N−H Imines

  摘要：

  Addition of lithium bis(trimethylsilyl)amide to perfluorinated ketones 1a-j affords (E)-N-TMS-ketimines 2a-j that are reduced in situ to afford racemic perfluoromethylated amine hydrochloride salts 3a-j in 54-97% yields. Solvolysis of the N-Si bond in MeOH leads to formation of bench-stable, isolable N-H imine Z/E isomer mixtures along with a methanol adduct. Enantioselective reduction of these three-component mixtures provides the first catalytic asymmetric synthesis of trifluoromethylated amines in 72-95% yields and 75-98% ee.

  DOI：

  10.1021/ol047431x

文献信息

• Unprecedented Catalytic Asymmetric Reduction of N−H Imines
  作者：Francis Gosselin、Paul D. O'Shea、Stéphanie Roy、Robert A. Reamer、Cheng-yi Chen、Ralph P. Volante

  DOI：10.1021/ol047431x

  日期：2005.1.1

  Addition of lithium bis(trimethylsilyl)amide to perfluorinated ketones 1a-j affords (E)-N-TMS-ketimines 2a-j that are reduced in situ to afford racemic perfluoromethylated amine hydrochloride salts 3a-j in 54-97% yields. Solvolysis of the N-Si bond in MeOH leads to formation of bench-stable, isolable N-H imine Z/E isomer mixtures along with a methanol adduct. Enantioselective reduction of these three-component mixtures provides the first catalytic asymmetric synthesis of trifluoromethylated amines in 72-95% yields and 75-98% ee.