dibenzo<1,6>naphthyridin-6(5H)-one | 789-42-4

• 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: dibenzo<1,6>naphthyridin-6(5H)-one
• 英文别名: 5H-quinolino[4,3-b]quinolin-6-one
• CAS: 789-42-4
• 化学式: C₁₆H₁₀N₂O
• 分子量: 246.268
• InChiKey: VZTIUGODXYTRAJ-UHFFFAOYSA-N

物化性质

• 熔点：
  354 °C
• 沸点：
  387.4±11.0 °C(Predicted)
• 密度：
  1.324±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  42
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-oxo-N-phenyl-1H-quinoline-3-carboxamide 在 PPA 作用下， 反应 5.0h， 以50%的产率得到dibenzo<1,6>naphthyridin-6(5H)-one
  参考文献：
  名称：

  Vijayalakshmi, S.; Rajendran, S. P., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1994, vol. 33, # 2, p. 159 - 162

  摘要：

  DOI：

文献信息

• A general and practicable synthesis of polycyclic heteroaromatic compounds. Part 1. Use of a putative quinolone-quinone-methide in the synthesis of polycyclic heteroaromatic compounds
  作者：Janet L. Asherson、Douglas W. Young

  DOI：10.1039/p19800000512

  日期：——

  A general and straightforward new synthesis of polycyclic heteroaromatic compounds has been developed. In the synthesis a putative quinolone-quinone-methide is generated in the presence of an aniline. The ensuing reaction results in a polycyclic heteroaromatic product. In the most useful approach, a hemiacetal (25) is prepared in one step from the parent quinolone and this is heated in the presence

  已经开发了多环杂芳族化合物的一般直接的新合成方法。在合成中，在苯胺的存在下会生成假定的喹诺酮-醌-甲基化物。随后的反应产生多环杂芳族产物。在最有用的方法中，一步法由母体喹诺酮制备半缩醛（25），并将其在芳族胺存在下加热，以高收率生产多环杂芳族化合物。该反应的区域特异性与Skraup合成中关于醌-甲基化物组分所预期的区域特异性相反。但是，就苯胺成分而言，区域特异性与Skraup合成中的区域特异性相同。
• Anti-tumour polycyclic carboxamides
  申请人：Baguley Charles Bruce

  公开号：US20050245561A1

  公开（公告）日：2005-11-03

  This invention relates to polycyclic carboxamide compounds of the formula (I) with cytotoxicity, processes for their preparation, pharmaceutical compositions containing them and their use in therapy, particularly I the treatment and/or prophylaxis of cellular proliferative disorders such a cancer.

  本发明涉及具有细胞毒性的多环羧酰胺化合物（I）的公式，它们的制备过程，包含它们的制药组合物以及它们在治疗中的应用，特别是在治疗和/或预防细胞增殖性疾病，如癌症方面的应用。
• ANTI-TUMOUR POLYCYCLIC CARBOXAMIDES
  申请人：Baguley Bruce Charles

  公开号：US20090156630A1

  公开（公告）日：2009-06-18

  This invention relates to polycyclic carboxamide compounds of the formula I: with cytotoxicity, processes for their preparation, pharmaceutical compositions containing them and their use in therapy, particularly in the treatment and/or prophylaxis of cellular proliferative disorders such as cancer.

  本发明涉及公式I的多环羧酰胺化合物，具有细胞毒性，其制备过程，包含它们的制药组合物及其在治疗中的使用，特别是在治疗和/或预防细胞增殖性疾病，如癌症中的应用。
• Nucleophilic Chlorination of 3-Formyl-4-hydroxy-quinolin-2(1H)-ones
  作者：Werner Fiala、Wolfgang Stadlbauer

  DOI：10.1002/prac.19933350203

  日期：——

  Chlorination of 1-substituted 3-formyl-4-hydroxy-2-quinolones (1a, b) with phosphorylchloride leads to 4-chloro-3-dichloromethylquinolones (2), which can be hydrolyzed to 4-chloro-3-formylquinolones (4). From the anilinomethylene quinolinediones (3), at low temperatures the formylquinolones 4 can be obtained directly, whereas at high temperatures cleavage of the tautomeric azomethine moiety followed by subsequent ring closure to the naphthyridines (7) takes place. With 1-unsubstituted 3-formyl-4-hydroxy-2-quinolones (1d) either the 3-dichloromethylquinolone (2d) or the 2,4-dichloro-3-dichloromethylquinoline (10) is obtained depending on the reaction conditions. Similar results are obtained with the 1-unsubstituted anilinomethylene compounds (3). Attempts to obtain the 3-formyl-2,4-dichloroquinoline (11) were unsuccessful because in all experiments the 2-chloro-group was converted to an oxygen function.
• Synthese von chinolin-kondensierten 2-Chinolonen und Cumarinen via Azidoverbindungen
  作者：Wolfgang Stadlbauer

  DOI：10.1007/bf00816872

  日期：1987.11