2,2-difluoro-4-methyl-1-phenylhexane-1,5-dione

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2-difluoro-4-methyl-1-phenylhexane-1,5-dione
• 化学式: C₁₃H₁₄F₂O₂
• 分子量: 240.25
• InChiKey: YUSFZOMXJHTPPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,2-difluoro-4-methyl-1-phenylhexane-1,5-dione 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以84%的产率得到4-fluoro-2-methyl-5-phenylphenol
  参考文献：
  名称：

  Mixed organofluorine-organosilicon chemistry. 8. One-pot synthesis of 2,2-difluoro-1,5 diketones from acylsilanes, trifluoromethyltrimethylsilane and enones, and their annulation reaction

  摘要：

  We describe the synthesis of 2,2-difluoro-1,5-diketones in a one-pot procedure from an acylsilane and trifluoromethyltrimethylsilane, via reaction of difluoroenoxysilanes and enones under electrophilic activation. These diketones are interesting building blocks for the synthesis of gem-difluoro enones or substituted fluorophenols, depending on the annulation conditions. The annulation proceeds with complete regioselectivity controlled by the fluorine substitution. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00224-5
• 作为产物：
  描述：

  2-甲基-1-丁烯-3-酮 、 三甲基硅基苯甲酮 、 (三氟甲基)三甲基硅烷 在 四氯化钛 、 Gingras' reagent 作用下， 生成 2,2-difluoro-4-methyl-1-phenylhexane-1,5-dione
  参考文献：
  名称：

  Mixed organofluorine-organosilicon chemistry. 8. One-pot synthesis of 2,2-difluoro-1,5 diketones from acylsilanes, trifluoromethyltrimethylsilane and enones, and their annulation reaction

  摘要：

  We describe the synthesis of 2,2-difluoro-1,5-diketones in a one-pot procedure from an acylsilane and trifluoromethyltrimethylsilane, via reaction of difluoroenoxysilanes and enones under electrophilic activation. These diketones are interesting building blocks for the synthesis of gem-difluoro enones or substituted fluorophenols, depending on the annulation conditions. The annulation proceeds with complete regioselectivity controlled by the fluorine substitution. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00224-5