methyl (E)-2-butyl-2-pentenoate | 165460-55-9

• 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: methyl (E)-2-butyl-2-pentenoate
• 英文别名: methyl (2E)-2-propylidenehexanoate
• CAS: 165460-55-9
• 化学式: C₁₀H₁₈O₂
• 分子量: 170.252
• InChiKey: MTYVDZMBFNKGRG-VQHVLOKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  12
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  methyl (E)-2-butyl-2-pentenoate 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以76%的产率得到(E)-2-butyl-2-pentenoic acid
  参考文献：
  名称：

  Structure-Activity Relationships of Unsaturated Analogs of Valproic Acid

  摘要：

  The principal metabolite of valproic acid (VPA), 2-ene VPA, appears to share most of VPA's pharmacological and therapeutic properties while lacking its hepatotoxicity and teratogenicity, thus making it a useful lead compound for the development of safer antiepileptic drugs. Analogues of 2-ene VPA were evaluated for anticonvulsant activity in mice using the subcutaneous pentylenetetrazole test. Cyclooctylideneacetic acid exhibited a potency markedly exceeding that of VPA itself with only modest levels of sedation. Potency, as either ED(50) or brain concentration, was highly correlated (r > 0.85) with volume and lipophilicity rather than with one of the shape parameters calculated by molecular modeling techniques, arguing against the existence of a specific receptor site. Instead, a role for the plasma membrane in mediating the anticonvulsant effect is suggested.

  DOI：

  10.1021/jm00017a024
• 作为产物：
  描述：

  2-(1-Methanesulfonyloxy-propyl)-hexanoic acid methyl ester 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成 methyl (E)-2-butyl-2-pentenoate
  参考文献：
  名称：

  Structure-Activity Relationships of Unsaturated Analogs of Valproic Acid

  摘要：

  The principal metabolite of valproic acid (VPA), 2-ene VPA, appears to share most of VPA's pharmacological and therapeutic properties while lacking its hepatotoxicity and teratogenicity, thus making it a useful lead compound for the development of safer antiepileptic drugs. Analogues of 2-ene VPA were evaluated for anticonvulsant activity in mice using the subcutaneous pentylenetetrazole test. Cyclooctylideneacetic acid exhibited a potency markedly exceeding that of VPA itself with only modest levels of sedation. Potency, as either ED(50) or brain concentration, was highly correlated (r > 0.85) with volume and lipophilicity rather than with one of the shape parameters calculated by molecular modeling techniques, arguing against the existence of a specific receptor site. Instead, a role for the plasma membrane in mediating the anticonvulsant effect is suggested.

  DOI：

  10.1021/jm00017a024