2-phenyl-1,2-dihydro-3H-pyrazolo[3,4-b]pyridin-3-one | 71290-75-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-phenyl-1,2-dihydro-3H-pyrazolo[3,4-b]pyridin-3-one
• 英文别名: 2-Phenyl-2,3-dihydro-1H-pyrazol-<3,4-b>-pyridin-3-on；2-phenyl-1,2-dihydro-pyrazolo[3,4-b]pyridin-3-one；2-Phenyl-2H-pyrazolo[3,4-B]pyridin-3-OL；2-phenyl-1H-pyrazolo[3,4-b]pyridin-3-one
• CAS: 71290-75-0
• 化学式: C₁₂H₉N₃O
• 分子量: 211.223
• InChiKey: JEKOHFKDAUSNTL-UHFFFAOYSA-N

物化性质

• 熔点：
  235-238 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  368.9±25.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-nitro-N-phenylnicotinamide 在 四羟基二硼 、 sodium hydroxide 作用下， 以 甲醇 为溶剂， 以21%的产率得到2-phenyl-1,2-dihydro-3H-pyrazolo[3,4-b]pyridin-3-one
  参考文献：
  名称：

  A B₂(OH)₄-Mediated Synthesis of 2-Substituted Indazolone and Its Application in a DNA-Encoded Library

  摘要：

  Indazolone cores are among the most common structural components in medicinal chemistry and can be found in many biologically active molecules. In this report, a mild and efficient approach to 2-substituted indazolones via B-2(OH)(4)-mediated reductive N-N bond formation is developed. This strategy features mild conditions, no request for a metal catalyst, and a wide scope for both aliphatic and aromatic amines. Meanwhile, this method was further successfully applied on DNA to construct indazolone cores for a DNA-encoded library. This will enable the production of a very attractive indazolone-cored library from simple amines and scaffolds, which will provide considerable diversity.

  DOI：

  10.1021/acs.orglett.0c02032

文献信息

• HAVERBEKE Y. VAN; MAQUESTIAU A.; EYNDE J. J. VANDEN, J. HETEROCYCL. CHEM. 1979, 16, NO 14, 773-777
  作者：HAVERBEKE Y. VAN、 MAQUESTIAU A.、 EYNDE J. J. VANDEN

  DOI：——

  日期：——
• A B₂(OH)₄-Mediated Synthesis of 2-Substituted Indazolone and Its Application in a DNA-Encoded Library
  作者：Yapeng Bao、Zongfa Deng、Jing Feng、Weiwei Zhu、Jin Li、Jinqiao Wan、Guansai Liu

  DOI：10.1021/acs.orglett.0c02032

  日期：2020.8.21

  Indazolone cores are among the most common structural components in medicinal chemistry and can be found in many biologically active molecules. In this report, a mild and efficient approach to 2-substituted indazolones via B-2(OH)(4)-mediated reductive N-N bond formation is developed. This strategy features mild conditions, no request for a metal catalyst, and a wide scope for both aliphatic and aromatic amines. Meanwhile, this method was further successfully applied on DNA to construct indazolone cores for a DNA-encoded library. This will enable the production of a very attractive indazolone-cored library from simple amines and scaffolds, which will provide considerable diversity.