(S)-1,1,1-trifluoro-5-methyl-2-(naphthalen-3-yl)hex-3-yne-2,5-diol | 1255152-71-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-1,1,1-trifluoro-5-methyl-2-(naphthalen-3-yl)hex-3-yne-2,5-diol
• CAS: 1255152-71-6
• 化学式: C₁₇H₁₅F₃O₂
• 分子量: 308.3
• InChiKey: JRJIZLUHVOGTTD-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.36
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (S)-1,1,1-trifluoro-5-methyl-2-(naphthalen-3-yl)hex-3-yne-2,5-diol 在 potassium hydroxide 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以86%的产率得到(S)-1,1,1-trifluoro-2-(naphthalen-3-yl)but-3-yn-2-ol
  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
• 作为产物：
  描述：

  (S)-5-(benzyloxy)-1,1,1-trifluoro-5-methyl-2-(naphthalen-3-yl)hex-3-yn-2-ol 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 6.0h， 以100%的产率得到(S)-1,1,1-trifluoro-5-methyl-2-(naphthalen-3-yl)hex-3-yne-2,5-diol
  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