ethyl 2-hydroxy-4-oxo-6-phenylcyclohex-2-enecarboxylate | 146497-72-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-hydroxy-4-oxo-6-phenylcyclohex-2-enecarboxylate
• 英文别名: Ethyl 4-hydroxy-2-oxo-6-phenylcyclohex-3-ene-1-carboxylate；ethyl 2-hydroxy-4-oxo-6-phenylcyclohex-2-ene-1-carboxylate
• CAS: 146497-72-5
• 化学式: C₁₅H₁₆O₄
• 分子量: 260.29
• InChiKey: NUCIKJKECPWVFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  ethyl 2-hydroxy-4-oxo-6-phenylcyclohex-2-enecarboxylate 在 肼 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以55%的产率得到4-Hydrazino-2-oxo-6-phenyl-cyclohex-3-enecarboxylic acid ethyl 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

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.
• 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。