methyl 2-hydroxy-4-oxo-6-phenylcyclohex-2-enecarboxylate | 146497-71-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-hydroxy-4-oxo-6-phenylcyclohex-2-enecarboxylate
• 英文别名: methyl 2-hydroxy-4-oxo-6-phenylcyclohex-2-en-1-oate；Methyl 4-hydroxy-2-oxo-6-phenylcyclohex-3-ene-1-carboxylate；methyl 2-hydroxy-4-oxo-6-phenylcyclohex-2-ene-1-carboxylate
• CAS: 146497-71-4
• 化学式: C₁₄H₁₄O₄
• 分子量: 246.263
• InChiKey: XVVYPBPJKJPYSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 2-hydroxy-4-oxo-6-phenylcyclohex-2-enecarboxylate 在 肼 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以76%的产率得到4-Hydrazino-2-oxo-6-phenyl-cyclohex-3-enecarboxylic acid methyl ester
  参考文献：
  名称：

  功能化的烯胺酮及其在杂环合成中的应用

  摘要：

  已经制备了一系列衍生自2，4-二氧代环己烷羧酸酯的烯胺酮。说明了在一些喹唑酮和咪唑并喹唑啉的合成中某些新衍生物的使用。

  DOI：

  10.1002/jhet.5570290602
• 作为产物：
  描述：

  methyl 2-methoxycarbonyl-3-phenyl-5-oxohexanoate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以82%的产率得到methyl 2-hydroxy-4-oxo-6-phenylcyclohex-2-enecarboxylate
  参考文献：
  名称：

  导致β-羟基酮酯的环化反应

  摘要：

  □研究的目的是合成β-二酮酯并评估其抗惊厥活性。在碳酸钾的存在下，甲基乙烯基酮与丙二酸二甲酯的反应得到未环化的产物，将其进行Clalsen缩合，得到2-羟基-4-氧代环己基-2-烯-1-酸甲酯（5a）。类似地，制备了其他环化的β-羟基酮酯，并且其光谱数据证实烯醇互变异构体比β-二酮互变异构体更优选。合成工作阐明了丙二酸酯向烯酮的迈克尔加成反应的反应途径。在测试的抗惊厥活性的中间体和产品中，发现2,2-双-（3-氧代丁基）丙二酸二甲酯（9a）具有抗惊厥性能。然而，

  DOI：

  10.1002/jps.2600830118

文献信息

• 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.
• Cyclization Reactions Leading to β-Hydroxyketo Esters
  作者：Jesse M. Nicholson、Ivan O. Edafiogho、Jacqueline A. Moore、Vida A. Farrar、K.R. Scott

  DOI：10.1002/jps.2600830118

  日期：1994.1

  the research was to synthesize β-diketo esters and to evaluate them for anticonvulsant activity. The reaction of methyl vinyl ketone with dimethyl malonate in the presence of potassium carbonate gave an uncyclized product that underwent a Clalsen condensation to yield methyl 2-hydroxy-4-oxocyclohex-2-en- 1-oate (5a). Similarly, other cyclized β-hydroxyketo esters were prepared, and their spectrometric

  □研究的目的是合成β-二酮酯并评估其抗惊厥活性。在碳酸钾的存在下，甲基乙烯基酮与丙二酸二甲酯的反应得到未环化的产物，将其进行Clalsen缩合，得到2-羟基-4-氧代环己基-2-烯-1-酸甲酯（5a）。类似地，制备了其他环化的β-羟基酮酯，并且其光谱数据证实烯醇互变异构体比β-二酮互变异构体更优选。合成工作阐明了丙二酸酯向烯酮的迈克尔加成反应的反应途径。在测试的抗惊厥活性的中间体和产品中，发现2,2-双-（3-氧代丁基）丙二酸二甲酯（9a）具有抗惊厥性能。然而，
• Functionalised enaminones and their use in heterocyclic synthesis
  作者：John V. Greenhill、Ibrahim Chaaban、Peter J. Steel

  DOI：10.1002/jhet.5570290602

  日期：1992.10

  A series of enaminones derived from 2,4-dioxocyclohexane carboxylic acid esters has been prepared. The use of some of the new derivatives in the synthesis of some quinazolones and imidazoloquinazolines is illustrated.

  已经制备了一系列衍生自2，4-二氧代环己烷羧酸酯的烯胺酮。说明了在一些喹唑酮和咪唑并喹唑啉的合成中某些新衍生物的使用。