6-bromo-5-phenyl-1H-pyrrolo[1,2-j]thieno[3,4-c]quinoline-2,7(9H,12bH)-dione | 1364232-74-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-bromo-5-phenyl-1H-pyrrolo[1,2-j]thieno[3,4-c]quinoline-2,7(9H,12bH)-dione
• 英文别名: 3-Bromo-2-phenyl-8-thia-5-azatetracyclo[10.4.0.01,5.07,11]hexadeca-2,7(11),9,15-tetraene-4,14-dione
• CAS: 1364232-74-5
• 化学式: C₂₀H₁₄BrNO₂S
• 分子量: 412.307
• InChiKey: ACGCJWUZXMKCFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  65.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-bromo-1-((3-iodothiophen-2-yl)methyl)-4-phenyl-1-azaspiro[4.5]deca-3,6,9-triene-2,8-dione 在 bis-triphenylphosphine-palladium(II) chloride 、 四丁基溴化铵 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 120.0 ℃ 、101.33 kPa 条件下， 反应 12.0h， 以40%的产率得到6-bromo-5-phenyl-1H-pyrrolo[1,2-j]thieno[3,4-c]quinoline-2,7(9H,12bH)-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