E-3-(3-bromo-1-propen-1-yl)-2-ethoxycarbonyl-4-phenylquinoline | 157139-90-7

• 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: E-3-(3-bromo-1-propen-1-yl)-2-ethoxycarbonyl-4-phenylquinoline
• CAS: 157139-90-7
• 化学式: C₂₁H₁₈BrNO₂
• 分子量: 396.283
• InChiKey: OESSNLKRTOUWBP-XYOKQWHBSA-N

物化性质

• 沸点：
  542.9±50.0 °C(predicted)
• 密度：
  1.363±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.49
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  39.19
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  E-3-(3-bromo-1-propen-1-yl)-2-ethoxycarbonyl-4-phenylquinoline 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 1.17h， 生成 (+/-)-3-<3-(sec-butylamino)prop-1-yl>-2-ethoxycarbonyl-4-phenylquinoline
  参考文献：
  名称：

  Synthesis of 4-Substituted 11-Phenyl-1,2,3,4-tetrahydro-5H-azepino[3,4-b]quinolin-5-one Derivatives as Potential Peripheral Benzodiazepine-Receptor Ligands

  摘要：

  The synthesis of semirigid analogs of PK 11195, the highly specific peripheral benzodiazepine-receptor ligand, is reported. Compound (4) underwent the Wittig reaction with acetaldehyde to give olefin (7) which after allylic bromination was aminated to give the omega-amino esters (10a-c). These compounds were then hydrogenated and cyclized in boiling toluene with DMAP as catalyst. The standard procedure failed in the case of compound (10b), thus other cyclization procedures were examinated.

  DOI：

  10.3987/com-93-6662
• 作为产物：
  描述：

  <(2-ethoxycarbonyl-4-phenylquinolin-3-yl)methyl>triphenylphosphonium bromide 在 N-溴代丁二酰亚胺(NBS) 、 potassium tert-butylate 、 过氧化苯甲酰 作用下， 以 苯 为溶剂， 反应 14.5h， 生成 E-3-(3-bromo-1-propen-1-yl)-2-ethoxycarbonyl-4-phenylquinoline
  参考文献：
  名称：

  Synthesis of 4-Substituted 11-Phenyl-1,2,3,4-tetrahydro-5H-azepino[3,4-b]quinolin-5-one Derivatives as Potential Peripheral Benzodiazepine-Receptor Ligands

  摘要：

  The synthesis of semirigid analogs of PK 11195, the highly specific peripheral benzodiazepine-receptor ligand, is reported. Compound (4) underwent the Wittig reaction with acetaldehyde to give olefin (7) which after allylic bromination was aminated to give the omega-amino esters (10a-c). These compounds were then hydrogenated and cyclized in boiling toluene with DMAP as catalyst. The standard procedure failed in the case of compound (10b), thus other cyclization procedures were examinated.

  DOI：

  10.3987/com-93-6662