1-{2,2-difluoro-1-[(2-methoxyethoxy)methoxy]ethenyl}-2-methoxybenzene | 1195887-00-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-{2,2-difluoro-1-[(2-methoxyethoxy)methoxy]ethenyl}-2-methoxybenzene
• 英文别名: 2,2-difluoro-1-(2'-methoxyethoxymethoxy)-1-(2''-methoxyphenyl)ethene；1-[2,2-Difluoro-1-(2-methoxyethoxymethoxy)ethenyl]-2-methoxybenzene
• CAS: 1195887-00-3
• 化学式: C₁₃H₁₆F₂O₄
• 分子量: 274.264
• InChiKey: UMAKKCDNRIXWCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  6

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 4.17h， 生成 1-{2,2-difluoro-1-[(2-methoxyethoxy)methoxy]ethenyl}-2-methoxybenzene
  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

• 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.