(E)-Perfluorohex-1-enyl phenyl ketone | 132868-69-0

• 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 phenyl ketone
• 英文别名: (E)-2,3,4,4,5,5,6,6,7,7,7-undecafluoro-1-phenylhept-2-en-1-one
• CAS: 132868-69-0
• 化学式: C₁₃H₅F₁₁O
• 分子量: 386.165
• InChiKey: YITPAYNABKILJO-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  25
• 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：

  (E)-Perfluorohex-1-enyl phenyl ketone 、 N-甲基乙二胺 以 乙醚 为溶剂， 反应 3.0h， 以88%的产率得到2-Fluoro-2-(1-methyl-2-nonafluorobutyl-imidazolidin-2-yl)-1-phenyl-ethanone
  参考文献：
  名称：

  Selectivity in the synthesis of fluorinated heterocycles from αβ-unsaturated perfluoroacyl derivatives (or their synthetic equivalents) and 1,2-bis-nucleophiles

  摘要：

  Reactions of vicinal diamines, aminoalcohols, aminothiols with synthetic equivalents of perfluoroenones 3 or alpha,beta-unsaturated perfluoroesters 6 gave regiospecifically new five member (imidazo or oxazolidines) or seven member fluorinated heterocycles (dia or thiazepines).

  DOI：

  10.1016/s0040-4039(00)73354-5
• 作为产物：
  描述：

  2,2,3,3,4,4,5,5,6,6,7,7,7-Tridecafluoro-1-phenyl-1-trimethylsilylheptan-1-ol 在 potassium fluoride 、 silica gel 作用下， 生成 (E)-Perfluorohex-1-enyl phenyl 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

• Synthesis of Polyfluorinated Nitrogen-Containing Heterocycles from Hemifluorinated Enones or Organofluorosilicon Building Blocks as Synthetic Equivalents
  作者：Frédéric Chanteau、Benoît Didier、Boniface Dondy、Pascale Doussot、Richard Plantier-Royon、Charles Portella

  DOI：10.1002/ejoc.200300671

  日期：2004.4

  equivalents with different bis(nucleophiles). These polyfluorinated building blocks were obtained by treatment of acylsilanes with perfluoro organometallic reagents. The method is general and has been applied to aliphatic, aromatic and carbohydrate derivatives, to give oxazolidines, imidazolidines, benzodia- and -thiazepines, quinolines and pyrimidines bearing both a fluorine atom and a perfluoroalkyl

  通过半氟化烯酮或有机氟硅合成等价物与不同双（亲核试剂）的杂环化反应制备了一系列多氟化杂环。这些多氟化结构单元是通过用全氟有机金属试剂处理酰基硅烷而获得的。该方法是通用的，已应用于脂肪族、芳香族和碳水化合物衍生物，以得到恶唑烷、咪唑烷、苯并二氮杂和硫氮杂、喹啉和嘧啶，在邻位同时带有氟原子和全氟烷基。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• Mixed organofluorine - organosilicon chemistry: reaction of perfluoroorganometallic reagents with benzoylsilane
  作者：Charles Portella、Boniface Dondy

  DOI：10.1016/s0040-4039(00)71224-x

  日期：1991.1

  Reaction of a perfluoroorganometallic (Mg or Li) reagent with benzoylsilanes gives, depending on the metal, the substituents and the reaction conditions, the F-alkyl phenyl trialkylsilyl carbinol , the F-alk-1-enyl phenyl ketone or the 1-phenyl-1-trialkylsilyloxy-F-alk-1-ene .

  全氟有机金属（Mg或Li）试剂与苯甲酰基硅烷的反应取决于金属，取代基和反应条件，它们分别是F-烷基苯基三烷基甲硅烷基甲醇，F-烷-1-烯基苯基酮或1-苯基- 1-三烷基甲硅烷氧基-F-链-1-烯。
• 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
• 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.
• Selectivity in the synthesis of fluorinated heterocycles from αβ-unsaturated perfluoroacyl derivatives (or their synthetic equivalents) and 1,2-bis-nucleophiles
  作者：B. Dondy、P. Doussot、M. Iznaden、M. Muzard、C. Portella

  DOI：10.1016/s0040-4039(00)73354-5

  日期：1994.6

  Reactions of vicinal diamines, aminoalcohols, aminothiols with synthetic equivalents of perfluoroenones 3 or alpha,beta-unsaturated perfluoroesters 6 gave regiospecifically new five member (imidazo or oxazolidines) or seven member fluorinated heterocycles (dia or thiazepines).