8-methyl-5H-chromeno[2,3-b]pyridin-5-one | 54629-27-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 8-methyl-5H-chromeno[2,3-b]pyridin-5-one
• 英文别名: 8-methyl-chromeno[2,3-b]pyridin-5-one；8-Methyl-5H-[1]benzopyrano[2,3-b]pyridin-5-one；8-methylchromeno[2,3-b]pyridin-5-one
• CAS: 54629-27-5
• 化学式: C₁₃H₉NO₂
• 分子量: 211.22
• InChiKey: JSEZFJACSOUKOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-methyl-5H-chromeno[2,3-b]pyridin-5-one 以76%的产率得到
  参考文献：
  名称：

  VILLANI F. J.; MANN T. A.; WEFER E. A.; HANNON J.; LARCA L. L.; LANDON M.+, J. MED. CHEM. , 1975, 18, NO 1, 1-8

  摘要：

  DOI：
• 作为产物：
  描述：

  2-m-tolyloxy-nicotinic acid 生成 8-methyl-5H-chromeno[2,3-b]pyridin-5-one
  参考文献：
  名称：

  Benzopyranopyridine derivatives. 1. Aminoalkyl derivatives of the azaxanthenes as bronchodilating agents

  摘要：

  The preparation of the four isomeric azaxanthones 3 and a number of their aromatic ring substituted derivatives is described. These ketones were converted into the title compounds which were examined for their biological properties. The most interesting compound in this series, the 1-methyl-4-piperidylidene derivative of 1-azaxanthene, shows the profile of an orally effective potent bronchodilating agent as well as a moderate antihistamine. Biological properties of this compound were compared to a number of antihistamines as well as known bronchodilating agents. Structure-activity relationships are also discussed.

  DOI：

  10.1021/jm00235a001

文献信息

• Synthesis of 1-Azaxanthones and 1-Azathioxanthones by Yb(OTf)3/TfOH Co-Catalyzed Intramolecular Friedel-Crafts Reaction
  作者：Weike Su、Can Jin、Jie Li

  DOI：10.3987/com-10-12029

  日期：——

  Intramolecular Friedel-Crafts cyclization of phenoxypyridine acids (3a-3j) and phenythiopyridine acids (4a-4i) to form 1-azaxanthones (1a-1j) and 1-azathioxanthones (2a-2i), respectively, was efficiently promoted by Yb(OTf) 3 /TfOH as co-catalysts. And a number of substrates could be cyclized in moderate to good yields.

  Yb(OTf) 有效促进苯氧基吡啶酸 (3a-3j) 和苯硫代吡啶酸 (4a-4i) 的分子内 Friedel-Crafts 环化分别形成 1-氮杂蒽酮 (1a-1j) 和 1-氮杂噻吨酮 (2a-2i) ) 3 /TfOH 作为助催化剂。并且许多底物可以以中等至良好的产率进行环化。