4-(benzyloxy)-4-methyl-1-(naphthalen-3-yl)pent-2-yn-1-one | 1255152-48-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-(benzyloxy)-4-methyl-1-(naphthalen-3-yl)pent-2-yn-1-one
• CAS: 1255152-48-7
• 化学式: C₂₃H₂₀O₂
• 分子量: 328.411
• InChiKey: YYGOFUWFRSHGCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.02
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-(benzyloxy)-4-methyl-1-(naphthalen-3-yl)pent-2-yn-1-one 、 (三氟甲基)三甲基硅烷 在 lithium acetate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成
  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：

  3-(benzyloxy)-3-methylbut-1-yne 、 2-萘甲酰氯 在 N,N-二异丙基乙胺 、 zinc dibromide 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以48%的产率得到4-(benzyloxy)-4-methyl-1-(naphthalen-3-yl)pent-2-yn-1-one
  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