10-nitrobenz[e]acephenanthrylene

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 10-nitrobenz[e]acephenanthrylene
• 英文别名: 1-Nitropentacyclo[10.7.1.02,7.08,20.013,18]icosa-1(19),2(7),3,5,8(20),9,11,13,15,17-decaene
• 化学式: C₂₀H₁₁NO₂
• 分子量: 297.313
• InChiKey: AFLSXNRUECEJQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-溴-2-(溴甲基)-4-硝基苯 在 palladium diacetate 、 正丁基锂 、 四丁基溴化铵 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 51.0h， 生成 10-nitrobenz[e]acephenanthrylene
  参考文献：
  名称：

  Synthesis of Spiro Polycyclic Aromatic Hydrocarbons by Intramolecular Palladium-Catalyzed Arylation

  摘要：

  The palladium-catalyzed intramolecular arylation reaction has been applied to the synthesis of the spiro polycyclic aromatic hydrocarbons and planar polycyclic aromatic hydrocarbons by formation of a six-membered ring. The reaction proceeds more readily with aryl bromides substituted with electron-withdrawing groups by using palladium acetate in N,N-dimethylformamide as the solvent. For the less reactive-p-methoxyaryl derivatives the use of LiI as an additive was shown to give the best results. The results obtained in the cyclization of nitro derivatives 21 and 23 suggest that the second step of the cyclization reaction is not an electrophilic substitution reaction.

  DOI：

  10.1021/jo962059n