13-Hydroxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-8-one | 75446-94-5

• 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-Hydroxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-8-one
• CAS: 75446-94-5
• 化学式: C₁₇H₁₃NO₂
• 分子量: 263.296
• InChiKey: CLHBFDFTEIMVAX-UHFFFAOYSA-N

物化性质

• 熔点：
  200 °C (decomp)
• 沸点：
  507.1±50.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  40.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  13-Hydroxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-8-one 在 盐酸 、 potassium dichromate 作用下， 以 丙酮 为溶剂， 反应 0.17h， 以94%的产率得到13a-hydroxy-5,6,13,13a-tetrahydro-8H-dibenzoquinolizine-8,13-dione
  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：

  9,10,14b,14c-tetrahydro-14c-hydroxy-7H-isoindolo[2',1':3,4]imidazo[5,1-a]isoquinolin-5-one 在 盐酸 作用下， 以 水 为溶剂， 反应 2.0h， 以55%的产率得到13-Hydroxy-5,6-dihydroisoquinolino[2,1-b]isoquinolin-8-one
  参考文献：
  名称：

  Coyle, J. D.; Challiner, J. F.; Haws, E. J., Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 1131 - 1132

  摘要：

  DOI：

文献信息

• Coyle, John D.; Challiner, John F.; Haws, Edmund J., Journal of Chemical Research, Miniprint, 1985, # 11, p. 3748 - 3761
  作者：Coyle, John D.、Challiner, John F.、Haws, Edmund J.、Newport, Graham L.

  DOI：——

  日期：——
• Close, Marjory; Coyle, John D.; Haws, Edmund J., Journal of Chemical Research, Miniprint, 1997, # 4, p. 701 - 719
  作者：Close, Marjory、Coyle, John D.、Haws, Edmund J.、Perry, Christopher J.

  DOI：——

  日期：——
• CHALLINER J. F.; HAWS E. J.; NEWPORT G. L.; COYLE J. D., J. HETEROCYCL. CHEM., 1980, 17, NO 5, 1131-1132
  作者：CHALLINER J. F.、 HAWS E. J.、 NEWPORT G. L.、 COYLE J. D.

  DOI：——

  日期：——
• Coyle, J. D.; Challiner, J. F.; Haws, E. J., Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 1131 - 1132
  作者：Coyle, J. D.、Challiner, J. F.、Haws, E. J.、Newport, G. L.

  DOI：——

  日期：——
• Oxidative Nitration and Bromination of Berbin-8-one
  作者：Jean-Fran腔is Stambach、Louis Jung

  DOI：10.3987/com-91-5777

  日期：——

  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.