3-(1-acetyl-5-(4-(dimethylamino)phenyl)-4,5-dihydro-1H-pyrazol-3-yl)-7-(dimethylamino)-4-hydroxy-2H-chromen-2-one | 1357486-66-8

• 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
• 英文名称: 3-(1-acetyl-5-(4-(dimethylamino)phenyl)-4,5-dihydro-1H-pyrazol-3-yl)-7-(dimethylamino)-4-hydroxy-2H-chromen-2-one
• 英文别名: 3-[2-Acetyl-3-[4-(dimethylamino)phenyl]-3,4-dihydropyrazol-5-yl]-7-(dimethylamino)-4-hydroxychromen-2-one
• CAS: 1357486-66-8
• 化学式: C₂₄H₂₆N₄O₄
• 分子量: 434.495
• InChiKey: NGIQKDZZKFJDFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  85.7
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 3-(1-acetyl-5-(4-(dimethylamino)phenyl)-4,5-dihydro-1H-pyrazol-3-yl)-7-(dimethylamino)-4-hydroxy-2H-chromen-2-one 以 二氯甲烷 为溶剂， 反应 6.0h， 以60%的产率得到3-[2-Acetyl-3-[4-(dimethylamino)phenyl]-3,4-dihydropyrazol-5-yl]-7-(dimethylamino)-4-methoxychromen-2-one
  参考文献：
  名称：

  Synthesis of 4-hydroxy-7-dimethylamino-3-pyrazolinylcoumarins and their polarity-sensitive properties

  摘要：

  Four 4-hydroxy-3-pyrazolinylcoumarin derivatives were synthesized and their UV-vis spectra in various compositions of MeOH and CH2Cl2 were measured. Among the prepared compounds, only one was found to exist mainly in the enol form in nonpolar solvents and the keto form in protic solvents, whereas the others are exclusively present in the enol forms regardless of solvent polarity. This polarity-sensitive property of 3-pyrazolinylcoumarins can be controlled by the electronic nature of the substituent at the 7-position of coumarin, the 1-position (nitrogen atom) of pyrazoline as well as the para-position of the benzene moiety. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.142
• 作为产物：
  描述：

  3-acetyl-7-(dimethylamino)-4-hydroxy-2H-chromen-2-one 在 哌啶 、 肼 作用下， 以 甲苯 为溶剂， 反应 17.0h， 生成 3-(1-acetyl-5-(4-(dimethylamino)phenyl)-4,5-dihydro-1H-pyrazol-3-yl)-7-(dimethylamino)-4-hydroxy-2H-chromen-2-one
  参考文献：
  名称：

  Synthesis of 4-hydroxy-7-dimethylamino-3-pyrazolinylcoumarins and their polarity-sensitive properties

  摘要：

  Four 4-hydroxy-3-pyrazolinylcoumarin derivatives were synthesized and their UV-vis spectra in various compositions of MeOH and CH2Cl2 were measured. Among the prepared compounds, only one was found to exist mainly in the enol form in nonpolar solvents and the keto form in protic solvents, whereas the others are exclusively present in the enol forms regardless of solvent polarity. This polarity-sensitive property of 3-pyrazolinylcoumarins can be controlled by the electronic nature of the substituent at the 7-position of coumarin, the 1-position (nitrogen atom) of pyrazoline as well as the para-position of the benzene moiety. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.11.142