5-phenyl-6-(phenylethynyl)-1H-pyrrolo[2,1-e]phenanthridine-2,7(9H,13bH)-dione | 1364232-81-4

• 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-phenyl-6-(phenylethynyl)-1H-pyrrolo[2,1-e]phenanthridine-2,7(9H,13bH)-dione
• 英文别名: 5-phenyl-6-(2-phenylethynyl)-9,13b-dihydro-1H-pyrrolo[2,1-e]phenanthridine-2,7-dione
• CAS: 1364232-81-4
• 化学式: C₃₀H₂₁NO₂
• 分子量: 427.502
• InChiKey: LCNRJHOJPGELEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  33
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  N-(2-iodobenzyl)-3-bromo-4-phenyl-1-azaspiro[4,5]deca-3,6,9-triene-2,8-dione 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 palladium diacetate 、 碳酸氢钠 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 5-phenyl-6-(phenylethynyl)-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