1-(N,N-diethylcarbamoyloxy)-2,2-difluoro-1-(3-benzothiophenyl)ethene | 1388708-00-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 1-(N,N-diethylcarbamoyloxy)-2,2-difluoro-1-(3-benzothiophenyl)ethene
• 英文别名: [1-(1-benzothiophen-3-yl)-2,2-difluoroethenyl] N,N-diethylcarbamate
• CAS: 1388708-00-6
• 化学式: C₁₅H₁₅F₂NO₂S
• 分子量: 311.352
• InChiKey: TVVFICRFJNIEKS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  57.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苯并噻吩-3-硼酸 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium hydrogen bifluoride 、 caesium carbonate 作用下， 以 甲醇 、 水 、 甲苯 为溶剂， 反应 4.0h， 生成 1-(N,N-diethylcarbamoyloxy)-2,2-difluoro-1-(3-benzothiophenyl)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.