3-((乙胺基)甲基)-4-羟基-6-甲基-2H-色烯-2-酮 | 100372-51-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 中文名称: 3-((乙胺基)甲基)-4-羟基-6-甲基-2H-色烯-2-酮
• 英文名称: 3-((ethylamino)methyl)-4-hydroxy-6-methyl-2H-chromen-2-one
• CAS: 100372-51-8
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: HVFBNMFWCZYBPJ-UHFFFAOYSA-N

物化性质

• 熔点：
  164 °C
• 沸点：
  401.9±45.0 °C(predicted)
• 密度：
  1.232±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.92
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  62.47
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-((乙胺基)甲基)-4-羟基-6-甲基-2H-色烯-2-酮 、 3-coumarinoylmethylpyridinium bromide 在 ammonium acetate 、 溶剂黄146 作用下， 反应 9.0h， 以40%的产率得到9-methyl-2-(2-oxo-2H-chromen-3-yl)-5H-chromeno[4,3-b]pyridin-5-one
  参考文献：
  名称：

  Synthesis of a new series of 2-(2-oxo-2H-chromen-3-yl)-5H-chromeno[4,3-b]pyridin-5-ones by two facile methods and evaluation of their antimicrobial activity

  摘要：

  A series of novel 2-(2-oxo-2H-chromen-3-yl)-5H-chromeno[4,3-b]pyridin-5-ones 4a-4l have been synthesized using two methodologies (using Mannich base of 4-hydroxy coumarin and 4-chloro-3-formyl coumarin) (Patel et al., 2012) and assayed for their antibacterial activity against gram-positive bacteria viz. Bacillus subtilis (MTCC 441), Staphylococcus aureus (MTCC 96) and gram-negative bacteria viz. Escherichia coli (MTCC 443), Salmonella typhimurium (MTCC 98). The compounds 4a-4l were also assayed for their antifungal activity against Aspergillus niger (MTCC 282) and Candida albicans (MTCC 227). All the compounds 4a-4l exhibited potent inhibitory activity against gram-positive bacteria compared to standard drugs at the tested concentrations. The compounds also showed appreciable activity against gram-negative bacteria as well as fungi. The compounds 4e, 4f, 4i, 4k, and 4l are found to be the most proficient members of the series and emerged as potential molecules for further development.

  DOI：

  10.1007/s00044-013-0489-4
• 作为产物：
  描述：

  聚合甲醛 、 4-羟基-6-甲基香豆素 、 乙胺 以 乙醇 为溶剂， 反应 0.5h， 以69%的产率得到3-((乙胺基)甲基)-4-羟基-6-甲基-2H-色烯-2-酮
  参考文献：
  名称：

  Synthesis of a new series of 2-(2-oxo-2H-chromen-3-yl)-5H-chromeno[4,3-b]pyridin-5-ones by two facile methods and evaluation of their antimicrobial activity

  摘要：

  A series of novel 2-(2-oxo-2H-chromen-3-yl)-5H-chromeno[4,3-b]pyridin-5-ones 4a-4l have been synthesized using two methodologies (using Mannich base of 4-hydroxy coumarin and 4-chloro-3-formyl coumarin) (Patel et al., 2012) and assayed for their antibacterial activity against gram-positive bacteria viz. Bacillus subtilis (MTCC 441), Staphylococcus aureus (MTCC 96) and gram-negative bacteria viz. Escherichia coli (MTCC 443), Salmonella typhimurium (MTCC 98). The compounds 4a-4l were also assayed for their antifungal activity against Aspergillus niger (MTCC 282) and Candida albicans (MTCC 227). All the compounds 4a-4l exhibited potent inhibitory activity against gram-positive bacteria compared to standard drugs at the tested concentrations. The compounds also showed appreciable activity against gram-negative bacteria as well as fungi. The compounds 4e, 4f, 4i, 4k, and 4l are found to be the most proficient members of the series and emerged as potential molecules for further development.

  DOI：

  10.1007/s00044-013-0489-4