(S)-2,2,2-trifluoro-1-(3-(4-methoxyphenyl)isoxazol-5-yl)-1-(naphthalen-2-yl)ethanol | 1255152-74-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-2,2,2-trifluoro-1-(3-(4-methoxyphenyl)isoxazol-5-yl)-1-(naphthalen-2-yl)ethanol
• 英文别名: (1S)-2,2,2-trifluoro-1-[3-(4-methoxyphenyl)-1,2-oxazol-5-yl]-1-naphthalen-2-ylethanol
• CAS: 1255152-74-9
• 化学式: C₂₂H₁₆F₃NO₃
• 分子量: 399.369
• InChiKey: IPNXKLWELHFOEC-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  55.5
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (S)-1,1,1-trifluoro-2-(naphthalen-3-yl)but-3-yn-2-ol 、 ALPHA-氯-4-甲氧基苯甲醛肟 在 potassium hydrogencarbonate 、 copper(II) sulfate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 2.0h， 以61%的产率得到(S)-2,2,2-trifluoro-1-(3-(4-methoxyphenyl)isoxazol-5-yl)-1-(naphthalen-2-yl)ethanol
  参考文献：
  名称：

  Cinchona Alkaloid-Catalyzed Asymmetric Trifluoromethylation of Alkynyl Ketones with Trimethylsilyl Trifluoromethane

  摘要：

  The first catalytic enantioselective trifluoromethylation of alkynyl ketones 1 with (trifluoromethyl)trimethylsilane is disclosed by an operationally simple procedure, based on the combination of ammonium bromide of bis-cinchona alkaloids with Me4NF to afford trifluoromethyl-substituted tertiary propargyl alcohols (up to 96% ee), which are the important chiral building blocks for pharmaceuticals. Biologically attractive aryl heteroaryl trifluoromethyl carbinols were also synthesized.

  DOI：

  10.1021/ol102189c

文献信息

• Cinchona Alkaloid-Catalyzed Asymmetric Trifluoromethylation of Alkynyl Ketones with Trimethylsilyl Trifluoromethane
  作者：Hiroyuki Kawai、Kentaro Tachi、Etsuko Tokunaga、Motoo Shiro、Norio Shibata

  DOI：10.1021/ol102189c

  日期：2010.11.19

  The first catalytic enantioselective trifluoromethylation of alkynyl ketones 1 with (trifluoromethyl)trimethylsilane is disclosed by an operationally simple procedure, based on the combination of ammonium bromide of bis-cinchona alkaloids with Me4NF to afford trifluoromethyl-substituted tertiary propargyl alcohols (up to 96% ee), which are the important chiral building blocks for pharmaceuticals. Biologically attractive aryl heteroaryl trifluoromethyl carbinols were also synthesized.