(2S)-2-propan-2-ylpentanoyl chloride | 1000183-80-1

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 酰卤
• 英文名称: (2S)-2-propan-2-ylpentanoyl chloride
• CAS: 1000183-80-1
• 化学式: C₈H₁₅ClO
• 分子量: 162.66
• InChiKey: UMJZUIUYKXEZMW-ZETCQYMHSA-N

物化性质

• 沸点：
  175.0±8.0 °C(Predicted)
• 密度：
  0.957±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2S)-2-propan-2-ylpentanoyl chloride 在 ammonium hydroxide 作用下， 以 乙腈 为溶剂， 反应 0.17h， 生成 (S)-Propylisopropylacetamide
  参考文献：
  名称：

  Potent Anticonvulsant Urea Derivatives of Constitutional Isomers of Valproic Acid

  摘要：

  Valproic acid (VPA) is a major antiepileptic drug (AED); however, its use is limited by two life-threatening side effects: teratogenicity and hepatotoxicity. Several constitutional isomers of VPA and their amide and urea derivatives were synthesized and evaluated in three different anticonvulsant animal models and a mouse model for AED-induced teratogenicity. The urea derivatives of three VPA constitutional isomers propylisopropylacetylurea, diisopropylacetylurea, and 2-ethyl-3-methyl-pentanoylurea displayed a broad spectrum of anticonvulsant activity in rats with a clear superiority over their corresponding amides and acids. Enanatiomers of propylisopropylacetylurea and propylisopropylacetamide revealed enantioselective anticonvulsant activity, whereas only enantiomers of propylisopropylacetylurea displayed enantioselective teratogenicity. These potent urea derivatives caused neural tube defects, but only at doses markedly exceeding their effective dose, whereas VPA showed no separation between its anticonvulsant activity and teratogenicity. The broad spectrum of anticonvulsant activity of the urea derivatives coupled with their wide safety margin make them potential, candidates to become new, potent AEDs.

  DOI：

  10.1021/jm7009233
• 作为产物：
  描述：

  (S)-Propylisopropylacetic Acid 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 (2S)-2-propan-2-ylpentanoyl chloride
  参考文献：
  名称：

  Potent Anticonvulsant Urea Derivatives of Constitutional Isomers of Valproic Acid

  摘要：

  Valproic acid (VPA) is a major antiepileptic drug (AED); however, its use is limited by two life-threatening side effects: teratogenicity and hepatotoxicity. Several constitutional isomers of VPA and their amide and urea derivatives were synthesized and evaluated in three different anticonvulsant animal models and a mouse model for AED-induced teratogenicity. The urea derivatives of three VPA constitutional isomers propylisopropylacetylurea, diisopropylacetylurea, and 2-ethyl-3-methyl-pentanoylurea displayed a broad spectrum of anticonvulsant activity in rats with a clear superiority over their corresponding amides and acids. Enanatiomers of propylisopropylacetylurea and propylisopropylacetamide revealed enantioselective anticonvulsant activity, whereas only enantiomers of propylisopropylacetylurea displayed enantioselective teratogenicity. These potent urea derivatives caused neural tube defects, but only at doses markedly exceeding their effective dose, whereas VPA showed no separation between its anticonvulsant activity and teratogenicity. The broad spectrum of anticonvulsant activity of the urea derivatives coupled with their wide safety margin make them potential, candidates to become new, potent AEDs.

  DOI：

  10.1021/jm7009233

文献信息

• Potent Anticonvulsant Urea Derivatives of Constitutional Isomers of Valproic Acid
  作者：Jakob Avi Shimshoni、Meir Bialer、Bogdan Wlodarczyk、Richard H. Finnell、Boris Yagen

  DOI：10.1021/jm7009233

  日期：2007.12.13

  Valproic acid (VPA) is a major antiepileptic drug (AED); however, its use is limited by two life-threatening side effects: teratogenicity and hepatotoxicity. Several constitutional isomers of VPA and their amide and urea derivatives were synthesized and evaluated in three different anticonvulsant animal models and a mouse model for AED-induced teratogenicity. The urea derivatives of three VPA constitutional isomers propylisopropylacetylurea, diisopropylacetylurea, and 2-ethyl-3-methyl-pentanoylurea displayed a broad spectrum of anticonvulsant activity in rats with a clear superiority over their corresponding amides and acids. Enanatiomers of propylisopropylacetylurea and propylisopropylacetamide revealed enantioselective anticonvulsant activity, whereas only enantiomers of propylisopropylacetylurea displayed enantioselective teratogenicity. These potent urea derivatives caused neural tube defects, but only at doses markedly exceeding their effective dose, whereas VPA showed no separation between its anticonvulsant activity and teratogenicity. The broad spectrum of anticonvulsant activity of the urea derivatives coupled with their wide safety margin make them potential, candidates to become new, potent AEDs.