5-(difluoromethyl)benzo[i]phenanthridine | 1610501-07-9

• 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: 5-(difluoromethyl)benzo[i]phenanthridine
• 英文别名: 6-(difluoromethyl)benzo[c]phenanthridine
• CAS: 1610501-07-9
• 化学式: C₁₈H₁₁F₂N
• 分子量: 279.289
• InChiKey: LYPXXLHHBJCHGR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.48
• 重原子数：
  21.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  12.89
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  2-(2-isocyanophenyl)naphthalene 在 disodium hydrogenphosphate 、 fac-tris(2-phenylpyridinato-N,C2')iridium(III) 、 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 5-(difluoromethyl)benzo[i]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

文献信息

• Silver-mediated oxidative C–H difluoromethylation of phenanthridines and 1,10-phenanthrolines
  作者：Sheng-Qing Zhu、Xiu-Hua Xu、Feng-Ling Qing

  DOI：10.1039/c7cc05411d

  日期：——

  A silver-mediated oxidative difluoromethylation of phenanthridines and 1,10-phenanthrolines with TMSCF2H is disclosed. This C―H difluoromethylation of N-containing polycyclic aromatics constitutes an efficient method for the regioselective syntheis of difluoromethylated N-heterocycles.

  公开了用TMCSF2H的菲啶和1,10-菲咯啉的银介导的氧化二氟甲基化。含氮多环芳族化合物的这种CHH二氟甲基化构成了二氟甲基化N杂环区域选择性合成的有效方法。