8-(1-acetyl-4,5-dihydro-5-(2,4-dimethoxyphenyl)-1H-pyrazol-3-yl)-7-hydroxy-4-methyl-2H-1-benzopyran-2-one | 1382626-91-6

• 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
• 英文名称: 8-(1-acetyl-4,5-dihydro-5-(2,4-dimethoxyphenyl)-1H-pyrazol-3-yl)-7-hydroxy-4-methyl-2H-1-benzopyran-2-one
• 英文别名: 8-[2-Acetyl-3-(2,4-dimethoxyphenyl)-3,4-dihydropyrazol-5-yl]-7-hydroxy-4-methylchromen-2-one
• CAS: 1382626-91-6
• 化学式: C₂₃H₂₂N₂O₆
• 分子量: 422.437
• InChiKey: DUCWYIDQKMMPQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  97.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  8-(1-acetyl-4,5-dihydro-5-(2,4-dimethoxyphenyl)-1H-pyrazol-3-yl)-7-hydroxy-4-methyl-2H-1-benzopyran-2-one 在 三溴化硼 、 水 作用下， 以 二氯甲烷 为溶剂， 以81%的产率得到8-(1-acetyl-4,5-dihydro-5-(2,4-dihydroxyphenyl)-1H-pyrazol-3-yl)-7-hydroxy-4-methyl-2H-1-benzopyran-2-one
  参考文献：
  名称：

  Synthesis of 4-methylcoumarin derivatives containing 4,5-dihydropyrazole moiety to scavenge radicals and to protect DNA

  摘要：

  A series of 4-methylcoumarin derivatives containing 4,5-dihydropyrazole moiety were synthesized and their antioxidant activities were evaluated in AAPH (2,2'-azobis(2-amidinopropane hydrochloride))-induced oxidation of DNA, and in trapping DPPH (2,2'-diphenyl-1-picrylhydrazyl) and ABTS(+center dot) (2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical), respectively. Among coumarin derivatives, 3a-d and 4a-c exhibited the termination of radical propagation-chains in AAPH-induced oxidation of DNA. The ortho dihydroxyphenyl substitution at 5 position and 1-unsubstitution of the 4,5-dihydroxylpyrazole was found enhancing the antioxidant activities of these coumarin derivatives. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.052
• 作为产物：
  描述：

  8-乙酰基-7-羟基-4-甲基-2H-1-苯并吡喃-2-酮 在 哌啶 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 14.0h， 生成 8-(1-acetyl-4,5-dihydro-5-(2,4-dimethoxyphenyl)-1H-pyrazol-3-yl)-7-hydroxy-4-methyl-2H-1-benzopyran-2-one
  参考文献：
  名称：

  Synthesis of 4-methylcoumarin derivatives containing 4,5-dihydropyrazole moiety to scavenge radicals and to protect DNA

  摘要：

  A series of 4-methylcoumarin derivatives containing 4,5-dihydropyrazole moiety were synthesized and their antioxidant activities were evaluated in AAPH (2,2'-azobis(2-amidinopropane hydrochloride))-induced oxidation of DNA, and in trapping DPPH (2,2'-diphenyl-1-picrylhydrazyl) and ABTS(+center dot) (2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical), respectively. Among coumarin derivatives, 3a-d and 4a-c exhibited the termination of radical propagation-chains in AAPH-induced oxidation of DNA. The ortho dihydroxyphenyl substitution at 5 position and 1-unsubstitution of the 4,5-dihydroxylpyrazole was found enhancing the antioxidant activities of these coumarin derivatives. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.03.052