(R)-1,1,1-trifluoro-5,5-dimethyl-2-(o-tolyl)hex-3-yn-2-ol | 1255152-55-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-1,1,1-trifluoro-5,5-dimethyl-2-(o-tolyl)hex-3-yn-2-ol
• 英文别名: (2R)-1,1,1-trifluoro-5,5-dimethyl-2-(2-methylphenyl)hex-3-yn-2-ol
• CAS: 1255152-55-6
• 化学式: C₁₅H₁₇F₃O
• 分子量: 270.295
• InChiKey: WIXJNTUDZOTYBK-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4,4-dimethyl-1-(o-tolyl)pent-2-yn-1-one 、 (三氟甲基)三甲基硅烷 在 2Br^(1-)*C₄₆H₅₂N₄O₂⁽²⁺⁾ 、 四甲基氟化铵 、 四丁基氟化铵 作用下， 以 二氯甲烷 、 甲苯 、 四氢呋喃 为溶剂， 反应 4.0h， 生成 (S)-1,1,1-trifluoro-5,5-dimethyl-2-(o-tolyl)hex-3-yn-2-ol 、 (R)-1,1,1-trifluoro-5,5-dimethyl-2-(o-tolyl)hex-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

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.