2-(2,4-dichloro-benzoyl)-3-oxo-butyric acid ethyl ester | 111544-92-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2,4-dichloro-benzoyl)-3-oxo-butyric acid ethyl ester
• 英文别名: Ethyl 2-(2,4-dichlorobenzoyl)-3-oxobutanoate
• CAS: 111544-92-4
• 化学式: C₁₃H₁₂Cl₂O₄
• 分子量: 303.142
• InChiKey: ZMAIQBVPUHQLCO-UHFFFAOYSA-N

物化性质

• 沸点：
  375.0±37.0 °C(Predicted)
• 密度：
  1.327±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2,4-dichloro-benzoyl)-3-oxo-butyric acid ethyl ester 在 氢氧化钾 、 ammonium hydroxide 、 氯化铵 作用下， 生成 2',4'-二氯苯甲酰基乙酸乙酯
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of a new series of substituted benzoyl-γ-butyrolactone derivatives

  摘要：

  A series of substituted benzoyl-gamma-butyrolactones (1-3) has been synthesized and tested for their ability to affect central dopaminergic and GABAergic function in comparison to gamma-butyrolactone (GEL). Similarly to GEL, alpha-, beta- and gamma-substituted GBLs 1-3 with one or more chlorine on the phenyl ring were found to induce central depressant effects in rats, though at different degrees. However, the test compounds modified dopamine (DA) metabolism in rat striatum differently from GEL. In fact, whereas GEL increased both DA and dihydroxyphenylacetic acid (DOPAC) content, GEL derivatives 1-3 increased DA levels, but reduced the DOPAC concentration. Moreover, some of them, unlike GEL, effectively antagonized pentylenetetrazole (PTZ)-induced seizures in mice. In particular, alpha-3,5-dichlorobenzoyl-GBL (1g) was effective at a dose as low as 36 mg/kg in decreasing the number of animals having convulsions. However, in vitro addition and in vivo administration of the test compounds failed to modify [S-35]-t-butylbicyclo-phosphorothionate ([S-35]-TBPS) binding, which is a very sensitive tool for revealing changes in the GABAergic function.

  DOI：

  10.1016/0223-5234(96)88290-0
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 2,4-二氯苯甲酰氯 在 magnesium 作用下， 以 四氯化碳 、 乙醚 、 乙醇 为溶剂， 反应 2.0h， 生成 2-(2,4-dichloro-benzoyl)-3-oxo-butyric acid ethyl ester
  参考文献：
  名称：

  Synthesis and pharmacological evaluation of a new series of substituted benzoyl-γ-butyrolactone derivatives

  摘要：

  A series of substituted benzoyl-gamma-butyrolactones (1-3) has been synthesized and tested for their ability to affect central dopaminergic and GABAergic function in comparison to gamma-butyrolactone (GEL). Similarly to GEL, alpha-, beta- and gamma-substituted GBLs 1-3 with one or more chlorine on the phenyl ring were found to induce central depressant effects in rats, though at different degrees. However, the test compounds modified dopamine (DA) metabolism in rat striatum differently from GEL. In fact, whereas GEL increased both DA and dihydroxyphenylacetic acid (DOPAC) content, GEL derivatives 1-3 increased DA levels, but reduced the DOPAC concentration. Moreover, some of them, unlike GEL, effectively antagonized pentylenetetrazole (PTZ)-induced seizures in mice. In particular, alpha-3,5-dichlorobenzoyl-GBL (1g) was effective at a dose as low as 36 mg/kg in decreasing the number of animals having convulsions. However, in vitro addition and in vivo administration of the test compounds failed to modify [S-35]-t-butylbicyclo-phosphorothionate ([S-35]-TBPS) binding, which is a very sensitive tool for revealing changes in the GABAergic function.

  DOI：

  10.1016/0223-5234(96)88290-0

文献信息

• 1120. Derivatives of 6-aminopenicillanic acid. Part VIII. Further analogues of 3-O-chorophenyl-5-methyl-4-isoxazolylpenicillin
  作者：J. C. Hanson、A. A. W. Long、J. H. C. Nayler、E. R. Stove

  DOI：10.1039/jr9650005976

  日期：——
• Synthesis and pharmacological evaluation of a new series of substituted benzoyl-γ-butyrolactone derivatives
  作者：G Cignarella、D Barlocco、D Pocar、F Clerici、MM Curzu、GL Gessa、F Fadda、M Serra、G Biggio

  DOI：10.1016/0223-5234(96)88290-0

  日期：1995.1

  A series of substituted benzoyl-gamma-butyrolactones (1-3) has been synthesized and tested for their ability to affect central dopaminergic and GABAergic function in comparison to gamma-butyrolactone (GEL). Similarly to GEL, alpha-, beta- and gamma-substituted GBLs 1-3 with one or more chlorine on the phenyl ring were found to induce central depressant effects in rats, though at different degrees. However, the test compounds modified dopamine (DA) metabolism in rat striatum differently from GEL. In fact, whereas GEL increased both DA and dihydroxyphenylacetic acid (DOPAC) content, GEL derivatives 1-3 increased DA levels, but reduced the DOPAC concentration. Moreover, some of them, unlike GEL, effectively antagonized pentylenetetrazole (PTZ)-induced seizures in mice. In particular, alpha-3,5-dichlorobenzoyl-GBL (1g) was effective at a dose as low as 36 mg/kg in decreasing the number of animals having convulsions. However, in vitro addition and in vivo administration of the test compounds failed to modify [S-35]-t-butylbicyclo-phosphorothionate ([S-35]-TBPS) binding, which is a very sensitive tool for revealing changes in the GABAergic function.