1-{2,4-dihydroxy-5-[(E)-2-phenyldiazen-1-yl]phenyl}ethan-1-one | 120196-22-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 偶氮苯
• 英文名称: 1-{2,4-dihydroxy-5-[(E)-2-phenyldiazen-1-yl]phenyl}ethan-1-one
• 英文别名: 1-(2,4-dihydroxy-5-phenylazo-phenyl)-ethanone；1-(2,4-Dihydroxy-5-phenylazo-phenyl)-aethanon；4.6-Dihydroxy-3-acetyl-azobenzol
• CAS: 120196-22-7
• 化学式: C₁₄H₁₂N₂O₃
• 分子量: 256.261
• InChiKey: HBKMLXLZGJJFAP-FOCLMDBBSA-N

物化性质

• 沸点：
  477.1±24.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  82.25
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-{2,4-dihydroxy-5-[(E)-2-phenyldiazen-1-yl]phenyl}ethan-1-one 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 水 、 potassium hydroxide 、 sodium hydroxide 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 73.0h， 生成 7-hydroxy-2-(4-methoxyphenyl)-6-[(E)-2-phenyldiazen-1-yl]-4H-chromen-4-one
  参考文献：
  名称：

  Antibacterial and free radical scavenging potential of synthesized 7-hydroxy-2-aryl-6-aryldiazenyl-4H-chromen-4-ones

  摘要：

  A series of 7-hydroxy-2-aryl-6-aryldiazenyl-4H-chromen-4-one derivatives (6a-m) was synthesized in quantitative yields and their structures were corroborated on the basis of FT-IR, H-1, C-13 NMR, ESI-MS, and elemental analysis data. The synthesized compounds were screened for in vitro antibacterial activities against a representative panel of Gram-positive and Gram-negative bacteria, as well as to evaluate their antioxidant potential using DPPH assay method. Bio-evaluation studies revealed that compounds 6c, 6d, 6e, 6j, and 6l exhibited moderate to good antibacterial activity against all the tested bacterial strains. Furthermore, from the antioxidant screening results, it has been observed that compounds 6c, 6e, and 6g manifested profound antioxidant potential (IC50 < 7.68 mu M) in comparison to the standard antioxidant ascorbic acid.

  DOI：

  10.1007/s00044-014-0938-8
• 作为产物：
  描述：

  2,4-二羟基苯乙酮 、 苯胺 在 盐酸 、 sodium nitrite 作用下， 以78%的产率得到1-{2,4-dihydroxy-5-[(E)-2-phenyldiazen-1-yl]phenyl}ethan-1-one
  参考文献：
  名称：

  Antibacterial and free radical scavenging potential of synthesized 7-hydroxy-2-aryl-6-aryldiazenyl-4H-chromen-4-ones

  摘要：

  A series of 7-hydroxy-2-aryl-6-aryldiazenyl-4H-chromen-4-one derivatives (6a-m) was synthesized in quantitative yields and their structures were corroborated on the basis of FT-IR, H-1, C-13 NMR, ESI-MS, and elemental analysis data. The synthesized compounds were screened for in vitro antibacterial activities against a representative panel of Gram-positive and Gram-negative bacteria, as well as to evaluate their antioxidant potential using DPPH assay method. Bio-evaluation studies revealed that compounds 6c, 6d, 6e, 6j, and 6l exhibited moderate to good antibacterial activity against all the tested bacterial strains. Furthermore, from the antioxidant screening results, it has been observed that compounds 6c, 6e, and 6g manifested profound antioxidant potential (IC50 < 7.68 mu M) in comparison to the standard antioxidant ascorbic acid.

  DOI：

  10.1007/s00044-014-0938-8

文献信息

• Neelakantam; Sitaraman, Proceedings - Indian Academy of Sciences, Section A, 1946, vol. 23, p. 16,18
  作者：Neelakantam、Sitaraman

  DOI：——

  日期：——
• Gore; Venkataraman, Proceedings - Indian Academy of Sciences, Section A, 1951, vol. 34, p. 368,378
  作者：Gore、Venkataraman

  DOI：——

  日期：——