(R)-2,2,2-trifluoro-1-(naphthalen-2-yl)-1-(5-phenylthiophen-2-yl)ethanol | 1255152-75-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (R)-2,2,2-trifluoro-1-(naphthalen-2-yl)-1-(5-phenylthiophen-2-yl)ethanol
• 英文别名: (1R)-2,2,2-trifluoro-1-naphthalen-2-yl-1-(5-phenylthiophen-2-yl)ethanol
• CAS: 1255152-75-0
• 化学式: C₂₂H₁₅F₃OS
• 分子量: 384.422
• InChiKey: ZVVXQZDXXRLVOW-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  48.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (S)-1,1,1-trifluoro-2-(naphthalen-2-yl)-6-phenylhexa-3,5-diyn-2-ol 在 sodium sulphide nonahydrate 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以42%的产率得到(R)-2,2,2-trifluoro-1-(naphthalen-2-yl)-1-(5-phenylthiophen-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.