1-{2,2-difluoro-1-[(2-methoxyethoxy)methoxy]ethenyl}-4-(trifluoromethyl)benzene | 1195886-85-1

• 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-{2,2-difluoro-1-[(2-methoxyethoxy)methoxy]ethenyl}-4-(trifluoromethyl)benzene
• 英文别名: 2,2-difluoro-1-(2-methoxy-ethoxymethoxy)-1-(4-trifluoromethylbenzene)ethene；2,2-difluoro-1-(2'-methoxyethoxymethoxy)-1-(4''-trifluoromethylphenyl)ethene；1-[2,2-Difluoro-1-(2-methoxyethoxymethoxy)ethenyl]-4-(trifluoromethyl)benzene
• CAS: 1195886-85-1
• 化学式: C₁₃H₁₃F₅O₃
• 分子量: 312.236
• InChiKey: ZMNFTNBSOLZPAS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1,1,1-三氟-2-[(2-甲氧基乙氧基)甲氧基]乙烷 在 N,N-二甲基丙烯基脲 、 bis-triphenylphosphine-palladium(II) chloride 、 caesium carbonate 、 zinc(II) chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 20.17h， 生成 1-{2,2-difluoro-1-[(2-methoxyethoxy)methoxy]ethenyl}-4-(trifluoromethyl)benzene
  参考文献：
  名称：

  Suzuki–Miyaura Coupling Reactions of Iodo(difluoroenol) Derivatives, Fluorinated Building Blocks Accessible at Near-Ambient Temperatures

  摘要：

  A recently developed method for the near-ambient generation of difluorovinylzinc reagents has facilitated the preparation of 1-(N,N-diethylcarbamoyloxy)-2,2-difluoro1-iodoethene and 2,2-difluoro-1-iodo-1-(2'-methoxyethoxymethoxy)ethene. The utility of these reagents has been investigated in Suzuki-Miyaura couplings with a range of potassium trifluoroborate coupling partners, with the scope of successful couplings proving wide. Deiodinated species appeared as significant side products, but a solvent change from i-PrOH to t-BuOH suppressed the pathway to these species and improved coupling yields.

  DOI：

  10.1021/jo3011705

文献信息

• One-pot near-ambient temperature syntheses of aryl(difluoroenol) derivatives from trifluoroethanol
  作者：Sara H. Kyne、Jonathan M. Percy、Robert D. C. Pullin、Joanna M. Redmond、Peter G. Wilson

  DOI：10.1039/c1ob06372c

  日期：——

  Difluoroalkenylzinc reagents prepared from 1-(2′-methoxy-ethoxymethoxy)-2,2,2-trifluoroethane and 1-(N,N-diethylcarbamoyloxy)-2,2,2-trifluoroethane at ice bath temperatures underwent Negishi coupling with a range of aryl halides in a convenient one pot procedure. While significant differences between the enol acetal and carbamate reagents were revealed, the Negishi protocol compared very favourably with alternative coupling procedures in terms of overall yields from trifluoroethanol.

  由1-(2'-甲氧基-乙氧基甲氧基)-2,2,2-三氟乙烷和1-(N,N-二乙基氨基甲酸酯)-2,2,2-三氟乙烷在冰浴温度下制备的氟代烯烃锌试剂，采用便捷的一锅法与多种芳基卤化物进行了Negishi偶联。尽管在醇醚和氨基甲酸酯试剂之间揭示出了显著差异，但与其他偶联程序相比，这种Negishi协议在三氟乙醇的整体产率方面表现非常优越。
• Preparation of a Stable Trifluoroborate Salt for the Synthesis of 1-Aryl-2,2-difluoro-enolethers and/or 2,2-Difluoro-1-aryl-ketones via Palladium-Mediated Cross-Coupling
  作者：Jason D. Katz、Blair T. Lapointe、Christopher J. Dinsmore

  DOI：10.1021/jo901789b

  日期：2009.11.20

  A bench-stable potassium trifluoroborate enol ether reagent has been prepared. This reagent is suitable for the incorporation of 2,2-difluoroenolethers into aryl and heteroaryl systems via palladium-mediated cross-coupling with suitable halide coupling partners.
• Suzuki–Miyaura Coupling Reactions of Iodo(difluoroenol) Derivatives, Fluorinated Building Blocks Accessible at Near-Ambient Temperatures
  作者：Peter G. Wilson、Jonathan M. Percy、Joanna M. Redmond、Adam W. McCarter

  DOI：10.1021/jo3011705

  日期：2012.8.3

  A recently developed method for the near-ambient generation of difluorovinylzinc reagents has facilitated the preparation of 1-(N,N-diethylcarbamoyloxy)-2,2-difluoro1-iodoethene and 2,2-difluoro-1-iodo-1-(2'-methoxyethoxymethoxy)ethene. The utility of these reagents has been investigated in Suzuki-Miyaura couplings with a range of potassium trifluoroborate coupling partners, with the scope of successful couplings proving wide. Deiodinated species appeared as significant side products, but a solvent change from i-PrOH to t-BuOH suppressed the pathway to these species and improved coupling yields.