ethyl 2-(2-chlorophenanthridin-6-yl)-2-fluoroacetate | 1610501-15-9

• 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-(2-chlorophenanthridin-6-yl)-2-fluoroacetate
• CAS: 1610501-15-9
• 化学式: C₁₇H₁₃ClFNO₂
• 分子量: 317.747
• InChiKey: DZBXZZONZTUTPC-UHFFFAOYSA-N

物化性质

• 熔点：
  108-109 °C
• 沸点：
  456.6±40.0 °C(predicted)
• 密度：
  1.333±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.62
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  39.19
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  溴氟乙酸乙酯 、 5-chloro-2-isocyano-1,1'-biphenyl 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70%的产率得到ethyl 2-(2-chlorophenanthridin-6-yl)-2-fluoroacetate
  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

文献信息

• Mn(<scp>iii</scp>)-mediated reactions of 2-isocyanobiaryl with 1,3-dicarbonyl compounds: efficient synthesis of 6-alkylated and 6-monofluoro-alkylated phenanthridines
  作者：Jia-Jia Cao、Xiang Wang、Shun-Yi Wang、Shun-Jun Ji

  DOI：10.1039/c4cc05324a

  日期：——

  Mn(III)-mediated reactions of 2-isocyanobiaryls with 1,3-dicarbonyl compounds were described for the construction of 6-alkylated and 6-monofluoro-alkylated phenanthridines in moderate to good yields. The reaction involves formation of two new C–C bonds and one C–C bond cleavage.

  该研究描述了 2-异氰基芳基与 1,3-二羰基化合物的 Mn(III) 介导反应，以中等至良好的收率生成 6-烷基化和 6-单氟烷基化菲啶。反应涉及两个新 C-C 键的形成和一个 C-C 键的裂解。