(E)-Perfluorohex-1-enyl 4-chlorophenyl ketone | 151961-16-9

• 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: (E)-Perfluorohex-1-enyl 4-chlorophenyl ketone
• 英文别名: (E)-1-(4-chlorophenyl)-2,3,4,4,5,5,6,6,7,7,7-undecafluorohept-2-en-1-one
• CAS: 151961-16-9
• 化学式: C₁₃H₄ClF₁₁O
• 分子量: 420.61
• InChiKey: QDGLHZOLYLNESF-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  甲基肼 、 (E)-Perfluorohex-1-enyl 4-chlorophenyl ketone 以 乙醚 为溶剂， 反应 5.0h， 以94%的产率得到3-(4'-chlorophenyl)-4-fluoro-1-methyl-5-(perfluorobutyl)pyrazole
  参考文献：
  名称：

  Efficient Synthesis of 4-Fluoro-5-(perfluoroalkyl)pyrazoles from Organofluorosilicon Building Blocks

  摘要：

  DOI：

  10.1002/1099-0690(200101)2001:1<187::aid-ejoc187>3.3.co;2-7
• 作为产物：
  描述：

  1-(4-Chloro-phenyl)-2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoro-1-trimethylsilanyl-heptan-1-ol 在 potassium fluoride 、 silica gel 作用下， 生成 (E)-Perfluorohex-1-enyl 4-chlorophenyl ketone
  参考文献：
  名称：

  Mixed organofluorine-organosilicon chemistry. 3. A highly efficient and convenient synthesis of aryl perfluoroalk-1-enyl ketones from perfluoroalkyl iodides and aroylsilanes

  摘要：

  A one-pot procedure is described to synthesize aryl perfluoroalkenyl ketones with high yields from perfluoroalkyl iodides and aroylsilanes. It consists of conversion of the iodide to the perfluoroorganomagnesium bromide followed by reaction with the aroylsilane, in ether, at low temperatures (-45-degrees-C). Warming to room temperature and addition of triethylamine accelerate the process leading quantitatively to the enones, which can be isolated in the pure E-configuration. The mechanism of this synthesis, involving a Brook rearrangement, is discussed. An alternative procedure is proposed to synthesize the same enones, with equivalent efficiency, from 1-aryl-1-(trimethylsilyl)perfluoroalkan-1-ols.

  DOI：

  10.1021/jo00076a028

文献信息

• Mixed organofluorine-organosilicon chemistry. 3. A highly efficient and convenient synthesis of aryl perfluoroalk-1-enyl ketones from perfluoroalkyl iodides and aroylsilanes
  作者：Boniface Dondy、Charles Portella

  DOI：10.1021/jo00076a028

  日期：1993.11

  A one-pot procedure is described to synthesize aryl perfluoroalkenyl ketones with high yields from perfluoroalkyl iodides and aroylsilanes. It consists of conversion of the iodide to the perfluoroorganomagnesium bromide followed by reaction with the aroylsilane, in ether, at low temperatures (-45-degrees-C). Warming to room temperature and addition of triethylamine accelerate the process leading quantitatively to the enones, which can be isolated in the pure E-configuration. The mechanism of this synthesis, involving a Brook rearrangement, is discussed. An alternative procedure is proposed to synthesize the same enones, with equivalent efficiency, from 1-aryl-1-(trimethylsilyl)perfluoroalkan-1-ols.
• Efficient Synthesis of 4-Fluoro-5-(perfluoroalkyl)pyrazoles from Organofluorosilicon Building Blocks
  作者：Jean-Philippe Bouillon、Benoît Didier、Boniface Dondy、Pascale Doussot、Richard Plantier-Royon、Charles Portella

  DOI：10.1002/1099-0690(200101)2001:1<187::aid-ejoc187>3.3.co;2-7

  日期：2001.1