6,6-Dimethyl-4-morpholin-4-yl-2-oxo-cyclohex-3-enecarboxylic acid methyl ester | 126750-27-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6,6-Dimethyl-4-morpholin-4-yl-2-oxo-cyclohex-3-enecarboxylic acid methyl ester
• 英文别名: 3-Cyclohexenecarboxylic acid, 6,6-dimethyl-4-(4-morpholyl)-2-oxo-, methyl ester；methyl 6,6-dimethyl-4-morpholin-4-yl-2-oxocyclohex-3-ene-1-carboxylate
• CAS: 126750-27-4
• 化学式: C₁₄H₂₁NO₄
• 分子量: 267.325
• InChiKey: DYHIUQXBZCECCJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6,6-Dimethyl-4-morpholin-4-yl-2-oxo-cyclohex-3-enecarboxylic acid methyl ester 、 丁酰氯 以65%的产率得到
  参考文献：
  名称：

  LAXVICH, F. A.;RUBINOV, D. B.;LIS, L. G.;RUBINOVA, I. L., ZH. ORGAN. XIMII, 25,(1989) N0, S. 2089-2094

  摘要：

  DOI：
• 作为产物：
  描述：

  吗啉 、 methyl 6,6-dimethyl-2-hydroxy-4-oxocyclohex-2-enecarboxylate 以 甲苯 为溶剂， 反应 3.0h， 以45%的产率得到6,6-Dimethyl-4-morpholin-4-yl-2-oxo-cyclohex-3-enecarboxylic acid methyl ester
  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

文献信息

• Lakhvich, F. A.; Rubinov, D. B.; Lis, L. G., Journal of Organic Chemistry USSR (English Translation), 1989, vol. 25, # 101, p. 1887 - 1891
  作者：Lakhvich, F. A.、Rubinov, D. B.、Lis, L. G.、Rubinova, I. L.

  DOI：——

  日期：——
• LAXVICH, F. A.;RUBINOV, D. B.;LIS, L. G.;RUBINOVA, I. L., ZH. ORGAN. XIMII, 25,(1989) N0, S. 2089-2094
  作者：LAXVICH, F. A.、RUBINOV, D. B.、LIS, L. G.、RUBINOVA, I. L.

  DOI：——

  日期：——
• Synthesis and anticonvulsant activity of enaminones
  作者：Ivan O. Edafiogho、Christine N. Hinko、Hyejung Chang、Jacqueline A. Moore、Dianna Mulzac、Jesse M. Nicholson、K. R. Scott

  DOI：10.1021/jm00093a012

  日期：1992.7

  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.