2,2,3,3,4,4,5,5,6,6,7,7,7-Tridecafluoro-1-phenyl-1-trimethylsilylheptan-1-ol | 132868-64-5

• 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: 2,2,3,3,4,4,5,5,6,6,7,7,7-Tridecafluoro-1-phenyl-1-trimethylsilylheptan-1-ol
• CAS: 132868-64-5
• 化学式: C₁₆H₁₅F₁₃OSi
• 分子量: 498.359
• InChiKey: GMLRBBXRXTULQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.49
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  全氟己基碘烷 、 三甲基硅基苯甲酮 在 乙基溴化镁 作用下， 以 乙醚 为溶剂， 生成 2,2,3,3,4,4,5,5,6,6,7,7,7-Tridecafluoro-1-phenyl-1-trimethylsilylheptan-1-ol
  参考文献：
  名称：

  混合有机氟-有机硅化学：全氟有机金属试剂与苯甲酰基硅烷的反应

  摘要：

  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。

  DOI：

  10.1016/s0040-4039(00)71224-x

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。
• 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.
• Mixed Organofluorine-Organosilicon Chemistry; 2. Synthesis of Alkyl and Aryl Perfluoroalkyl Trialkylsilyl Carbinols
  作者：Boniface Dondy、Pascale Doussot、Charles Portella

  DOI：10.1055/s-1992-26287

  日期：——

  1-Alkyl- and 1-aryl-1-trialkylsilyl-1-perfluoroalkanols, a new class of alcohols, were synthesized from acyl or aroylsilanes and perfluoroorganomagnesium reagents, and their spectroscopic characteristics are described.

  1-烷基和1-芳基-1-三烷基硅烷-1-全氟烷醇是一类新型醇化合物，通过酰基或芳酰基硅烷与全氟有机镁试剂合成，并描述了它们的光谱特征。