6-bromo-5-p-tolyl-1H-pyrrolo[2,1-e]phenanthridine-2,7-(9H,13bH)-dione | 1364232-58-5

• 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: 6-bromo-5-p-tolyl-1H-pyrrolo[2,1-e]phenanthridine-2,7-(9H,13bH)-dione
• 英文别名: 6-bromo-5-(4-methylphenyl)-9,13b-dihydro-1H-pyrrolo[2,1-e]phenanthridine-2,7-dione
• CAS: 1364232-58-5
• 化学式: C₂₃H₁₈BrNO₂
• 分子量: 420.305
• InChiKey: NITPNYQKIKUZNP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  在 bis-triphenylphosphine-palladium(II) chloride 、 N-溴代丁二酰亚胺(NBS) 、 四丁基溴化铵 、 水 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 120.0 ℃ 、101.33 kPa 条件下， 反应 36.0h， 生成 6-bromo-5-p-tolyl-1H-pyrrolo[2,1-e]phenanthridine-2,7-(9H,13bH)-dione
  参考文献：
  名称：

  Intramolecular ipso-Halocyclization of 4-(p-Unsubstituted-aryl)-1-alkynes Leading to Spiro[4,5]trienones: Scope, Application, and Mechanistic Investigations

  摘要：

  A new, general method for the synthesis of spiro[4,5]trienores is described by the intramolecular ipso-halocyclization of 4-(p-unsubstituted-aryl)-1-alkynes. In the presence of halide electrophiles, a variety of 4-(p-unsubstituted-aryl)-1-alkynes underwent the intramolecular ipso-halocyclization with water smoothly, affording the corresponding halo-substituted spiro[4,5]trienones in moderate to good yields. The obtained spiro[4,5]trienones can be applied in constructing the azaquaternary tricyclic skeleton via Pd-catalyzed Heck reaction. Notably, the prepared spiro[4,5]trienones and azaquaternary tricycles are of importance in the areas of pharmaceuticals and agrochemicals. The mechanism of the intramolecular ipso-halocyclization reaction is also discussed according to the O-18-labeling experiments and DFT calculations.

  DOI：

  10.1021/jo300037n