Methyl 6-methyl-4-morpholin-4-yl-2-oxocyclohex-3-ene-1-carboxylate | 142457-97-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 6-methyl-4-morpholin-4-yl-2-oxocyclohex-3-ene-1-carboxylate
• CAS: 142457-97-4
• 化学式: C₁₃H₁₉NO₄
• 分子量: 253.298
• InChiKey: XGRFCKYHDGSSJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-戊烯-2-酮 在 sodium methylate 作用下， 以 甲苯 为溶剂， 反应 6.5h， 生成 Methyl 6-methyl-4-morpholin-4-yl-2-oxocyclohex-3-ene-1-carboxylate
  参考文献：
  名称：

  Synthesis and anticonvulsant activity of enaminones

  摘要：

  A new series of novel enaminones has been synthesized from cyclic beta-dicarbonyl precursors which were condensed with morpholine, pyrrolidine, phenethylamine, hydrazines, substituted benzyl amines, and substituted anilines. These compounds were subsequently evaluated for anticonvulsant activity in a variety of anticonvulsant models by the National Institute of Neurological and Communicative Disorders and Stroke and in our laboratory. Several of these compounds exhibited potent anticonvulsant activity with a remarkable lack of neurotoxicity. The most active analog, methyl 4-[(p-chlorophenyl)amino]-6-methyl-2-oxo-cyclohex-3-en-1-oate (27), was protective in the maximal electroshock (MES) seizure test in the rat with an oral ED50 of 5.8 mg/kg with no toxicity noted at doses up to 380 mg/kg, thus providing a protective index (TD50/ED50) of > 65.5. A similar protective index for 27 was noted upon intraperitoneal (ip) administration in mice. The anticonvulsant effect of 27 occurred within 15 min of administration and the compound remained active beyond 4 h. Compound 27 was also active in the rat corneal kindled model. The application of Free-Wilson analysis to structure-activity correlation in this series is discussed.

  DOI：

  10.1021/jm00093a012