ethyl 2-(dibenzo[i,k]phenanthridin-5-yl)-2,2-difluoroacetate | 1610500-94-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: ethyl 2-(dibenzo[i,k]phenanthridin-5-yl)-2,2-difluoroacetate
• CAS: 1610500-94-1
• 化学式: C₂₅H₁₇F₂NO₂
• 分子量: 401.412
• InChiKey: AAGXAQAOYGOEIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.35
• 重原子数：
  30.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  39.19
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-(dibenzo[i,k]phenanthridin-5-yl)-2,2-difluoroacetate 在 potassium carbonate 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 以90%的产率得到5-(difluoromethyl)dibenzo[i,k]phenanthridine
  参考文献：
  名称：

  Visible-Light-Mediated Fluoroalkylation of Isocyanides with Ethyl Bromofluoroacetates: Unified Synthesis of Mono- and Difluoromethylated Phenanthridine Derivatives

  摘要：

  A practical and unified strategy has been described for the preparation of mono- and difluoromethylated phenanthridine derivatives using a visible-light-promoted alkylation and decarboxylation sequence from biphenyl isocyanides with ethyl bromofluoroacetate (EBFA) or ethyl bromodifluoroacetate (EBDFA). These reactions could be carried out at room temperature in good to excellent chemical yields. Both stepwise and one-pot procedures have been developed, which makes this strategy more attractive.

  DOI：

  10.1021/ol501081h
• 作为产物：
  描述：

  二氟溴乙酸乙酯 、 9-(2-isocyanophenyl)phenanthrene 在 disodium hydrogenphosphate 、 fac-tris(2-phenylpyridinato-N,C2')iridium(III) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以75%的产率得到ethyl 2-(dibenzo[i,k]phenanthridin-5-yl)-2,2-difluoroacetate
  参考文献：
  名称：

  Visible-Light-Mediated Fluoroalkylation of Isocyanides with Ethyl Bromofluoroacetates: Unified Synthesis of Mono- and Difluoromethylated Phenanthridine Derivatives

  摘要：

  A practical and unified strategy has been described for the preparation of mono- and difluoromethylated phenanthridine derivatives using a visible-light-promoted alkylation and decarboxylation sequence from biphenyl isocyanides with ethyl bromofluoroacetate (EBFA) or ethyl bromodifluoroacetate (EBDFA). These reactions could be carried out at room temperature in good to excellent chemical yields. Both stepwise and one-pot procedures have been developed, which makes this strategy more attractive.

  DOI：

  10.1021/ol501081h