13-nitro-5,6-dihydro-8H-dibenzoquinolizin-8-one | 138770-56-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 13-nitro-5,6-dihydro-8H-dibenzoquinolizin-8-one
• 英文别名: 13-nitro-5,6-dihydroisoquinolino[2,1-b]isoquinolin-8-one
• CAS: 138770-56-6
• 化学式: C₁₇H₁₂N₂O₃
• 分子量: 292.294
• InChiKey: KTLFWJBAQDLXQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.13
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  65.14
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  13-nitro-5,6-dihydro-8H-dibenzoquinolizin-8-one 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以81%的产率得到13-nitro-5,6,13,13a-tetrahydro-8H-dibenzoquinolizin-8-one
  参考文献：
  名称：

  Oxidative Nitration and Bromination of Berbin-8-one

  摘要：

  In presence of two equivalents of nitric acid berbin-8-one (1) could be oxidized and nitrated to give 13-nitro-13,13a-dehydroberbin-8-one (2) in good yield. In the same way berbin-8-one (1) was made to react with N-bromosuccinimide to afford the 13-bromo analogue (3). The mechanism of the nitrative oxidation was studied. This oxidation is initiated by nitrogen dioxide from nitrous fumes included in the nitric acid. The oxidative nitration is accelerated by increasing the acidity or temperature of the medium. A radical mechanism which involves the 13,13a-dehydro-berbin-8-one (9) as intermediate of the reaction is postulated and discussed. The potential of this synthetic route was investigated.

  DOI：

  10.3987/com-91-5777
• 作为产物：
  描述：

  5,6,13,13a-Tetrahydro-8H-dibenzo[a,g]chinolizin-8-on 在 硫酸 、 硝酸 作用下， 以 溶剂黄146 为溶剂， 反应 0.3h， 以87%的产率得到13-nitro-5,6-dihydro-8H-dibenzoquinolizin-8-one
  参考文献：
  名称：

  Oxidative Nitration and Bromination of Berbin-8-one

  摘要：

  In presence of two equivalents of nitric acid berbin-8-one (1) could be oxidized and nitrated to give 13-nitro-13,13a-dehydroberbin-8-one (2) in good yield. In the same way berbin-8-one (1) was made to react with N-bromosuccinimide to afford the 13-bromo analogue (3). The mechanism of the nitrative oxidation was studied. This oxidation is initiated by nitrogen dioxide from nitrous fumes included in the nitric acid. The oxidative nitration is accelerated by increasing the acidity or temperature of the medium. A radical mechanism which involves the 13,13a-dehydro-berbin-8-one (9) as intermediate of the reaction is postulated and discussed. The potential of this synthetic route was investigated.

  DOI：

  10.3987/com-91-5777