2,2-difluoro-1-(2'-methoxyethoxymethoxy)-1-iodoethene | 1388707-61-6

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 乙烯基卤化物
• 英文名称: 2,2-difluoro-1-(2'-methoxyethoxymethoxy)-1-iodoethene
• 英文别名: 1,1-Difluoro-2-iodo-2-(2-methoxyethoxymethoxy)ethene
• CAS: 1388707-61-6
• 化学式: C₆H₉F₂IO₃
• 分子量: 294.037
• InChiKey: KRGKKDVGKRKQFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4-氰基苯基)三氟硼酸钾 、 2,2-difluoro-1-(2'-methoxyethoxymethoxy)-1-iodoethene 在 bis-triphenylphosphine-palladium(II) chloride 、 caesium carbonate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 18.0h， 以59%的产率得到2,2-difluoro-1-(2'-methoxyethoxymethoxy)-1-(4''-cyanophenyl)ethene
  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
• 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 、 zinc(II) chloride 、 lithium diisopropyl amide 、 碘 作用下， 以 四氢呋喃 为溶剂， 反应 2.17h， 以50%的产率得到2,2-difluoro-1-(2'-methoxyethoxymethoxy)-1-iodoethene
  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