2,2-difluoro-1-(2'-methoxyethoxymethoxy)-1-(4-isoquinolyl)ethene | 1388707-91-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 2,2-difluoro-1-(2'-methoxyethoxymethoxy)-1-(4-isoquinolyl)ethene
• 英文别名: 4-[2,2-Difluoro-1-(2-methoxyethoxymethoxy)ethenyl]isoquinoline
• CAS: 1388707-91-2
• 化学式: C₁₅H₁₅F₂NO₃
• 分子量: 295.286
• InChiKey: FWNHVGFQBXEINX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  40.6
• 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 、 叔丁醇 为溶剂， 反应 20.17h， 生成 2,2-difluoro-1-(2'-methoxyethoxymethoxy)-1-(4-isoquinolyl)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

文献信息

• 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.