ethyl-isobutyl-malonic acid diethyl ester | 123647-93-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl-isobutyl-malonic acid diethyl ester
• 英文别名: Aethyl-isobutyl-malonsaeure-diaethylester；Diethyl 2-ethyl-2-isobutylmalonate；diethyl 2-ethyl-2-(2-methylpropyl)propanedioate
• CAS: 123647-93-8
• 化学式: C₁₃H₂₄O₄
• 分子量: 244.331
• InChiKey: CXSIESQPWSWLSU-UHFFFAOYSA-N

物化性质

• 沸点：
  234-240 °C
• 密度：
  0.975±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl-isobutyl-malonic acid diethyl ester 在 氢氧化钾 作用下， 生成 ethyl-isobutyl-malonic acid
  参考文献：
  名称：

  Tiffeneau, Bulletin de la Societe Chimique de France, 1923, vol. <4> 33, p. 186

  摘要：

  DOI：
• 作为产物：
  描述：

  溴代异丁烷 、 乙基丙二酸二乙酯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 ethyl-isobutyl-malonic acid diethyl ester
  参考文献：
  名称：

  Further Branching of Valproate-Related Carboxylic Acids Reduces the Teratogenic Activity, but Not the Anticonvulsant Effect

  摘要：

  In the present study, compounds derived from the anticonvulsant drug valproic acid (VPA, 2-n-propylpentanoic acid) and analogues known to be teratogenic were synthesized with an additional carbon-branching in one of the side chains. The substances were tested for their ability to induce anticonvulsant-activity and sedation in adult mice, and neural tube defects (exencephaly) in the offspring of pregnant animals (Han:NMRI mice). In all cases, the rates of exencephaly, embryolethality, and fetal weight retardation induced by the methyl-branched derivatives were very low when compared to those of the parent compounds, These novel compounds exhibited anticonvulsant activity which was not significantly different from that of VPA. Neurotoxicity was considerably lower for some compounds as compared to VPA. Anticonvulsant activity and neurotoxicity of branched short chain fatty acids are far less structure-dependent and not related to teratogenic potency. Within this series of compounds, (+/-)-4-methyl-2-n-propyl-4-pentenoic acid and (+/-)-2-isobutyl-4-pentenoic acid exhibited the most favorable profile in regard to high anticonvulsant effect, low sedation, and teratogenicity. Valproic acid analogues with additional methyl branching may be valuable antiepileptic agents with low teratogenic potential.

  DOI：

  10.1021/tx950216s

文献信息

• Some N-Aryl Barbituric Acids. II
  作者：Johannes S. Buck

  DOI：10.1021/ja01301a069

  日期：1936.10
• Hjort; Dox, Journal of Pharmacology and Experimental Therapeutics, 1929, vol. 35, p. 155,156
  作者：Hjort、Dox

  DOI：——

  日期：——
• Shonle; Moment, Journal of the American Chemical Society, 1923, vol. 45, p. 248
  作者：Shonle、Moment

  DOI：——

  日期：——
• Di- and Trialkyl Barbituric Acids
  作者：H. A. Shonle、Wilbur J. Doran

  DOI：10.1021/ja01299a015

  日期：1936.8
• Thiobarbiturates. II
  作者：Ellis Miller、James C. Munch、Frank S. Crossley、Walter H. Hartung

  DOI：10.1021/ja01298a007

  日期：1936.7