1-<(tert-Butyldimethylsilyl)oxy>-1-phenylperfluorohept-1-ene | 132868-68-9

• 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: 1-<(tert-Butyldimethylsilyl)oxy>-1-phenylperfluorohept-1-ene
• 英文别名: 1-Phenyl-1-<(tert-butyldimethylsilyl)oxy>perfluoroheptene；tert-butyl-(2,3,3,4,4,5,5,6,6,7,7,7-dodecafluoro-1-phenylhept-1-enoxy)-dimethylsilane
• CAS: 132868-68-9
• 化学式: C₁₉H₂₀F₁₂OSi
• 分子量: 520.434
• InChiKey: JKXZIZSHZMLDNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.45
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  1-<(tert-Butyldimethylsilyl)oxy>-1-phenylperfluorohept-1-ene 在 盐酸 作用下， 以 乙醚 为溶剂， 生成 1-Hydroperfluorohexyl phenyl ketone
  参考文献：
  名称：

  Mixed organofluorine-organosilicon chemistry. 4. Perfluoroenoxysilanes: synthesis and reactivity

  摘要：

  1-Alkyl (or aryl)-1-[(trialkylsilyl)oxy]perfluoroalk-1-enes were synthesized from acylsilanes and perfluoroalkyl iodides. Perfluoroorganolithium and magnesium were used for aliphatic and aromatic derivatives, respectively. These enoxysilanes have nucleophilic as well as electrophilic properties. They are enolate equivalents, leading to 2-hydroperfluoroalkyl ketones on hydrolysis, or aldol products. With good nucleophiles like amines, they react as electron poor alkenes to give beta-enamino ketones.

  DOI：

  10.1021/jo00076a029
• 作为产物：
  描述：

  全氟己基碘烷 、 硅烷,苯甲酰(1,1-二甲基乙基)二甲基- 在 乙基溴化镁 作用下， 生成 1-<(tert-Butyldimethylsilyl)oxy>-1-phenylperfluorohept-1-ene
  参考文献：
  名称：

  Mixed organofluorine-organosilicon chemistry. 4. Perfluoroenoxysilanes: synthesis and reactivity

  摘要：

  1-Alkyl (or aryl)-1-[(trialkylsilyl)oxy]perfluoroalk-1-enes were synthesized from acylsilanes and perfluoroalkyl iodides. Perfluoroorganolithium and magnesium were used for aliphatic and aromatic derivatives, respectively. These enoxysilanes have nucleophilic as well as electrophilic properties. They are enolate equivalents, leading to 2-hydroperfluoroalkyl ketones on hydrolysis, or aldol products. With good nucleophiles like amines, they react as electron poor alkenes to give beta-enamino ketones.

  DOI：

  10.1021/jo00076a029

文献信息

• 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.