methyl 2-hydroxy-4-oxo-6-phenylcyclohex-2-en-1-oate | 151777-66-1

• 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-en-1-oate
• 英文别名: methyl 4-hydroxy-2-oxo-6-phenylcyclohex-3-ene-1-carboxylate
• CAS: 151777-66-1
• 化学式: C₁₄H₁₄O₄
• mdl: MFCD00451047
• 分子量: 246.263
• InChiKey: LKFZUQQAAOFZFT-UHFFFAOYSA-N

物化性质

• 沸点：
  384.5±42.0 °C(Predicted)
• 密度：
  1.275±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.97
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 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：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  methyl 2-hydroxy-4-oxo-6-phenylcyclohex-2-en-1-oate 在 盐酸胍 、 sodium 作用下， 以 甲苯 为溶剂， 反应 8.0h， 生成 ethyl 2-oxo-6-phenyl-4-pyrrolidinocyclohex-3-en-1-oate
  参考文献：
  名称：

  烯胺酯的合成，反应和初步评价

  摘要：

  这项工作的目的是设计具有潜在医学特性的烯胺酯。β-羟基酮酯与伯或仲胺之间的反应分别产生仲或叔烯胺酯。在酸性，碱性和中性介质中测定烯胺酯的紫外光谱。与中性介质相比，该光谱在酸性介质中具有七色移。烯胺酯为各种反应提供了亲核和亲电子位点。因此，烯胺酮酯仅转化为烯胺酰胺和O-烷基化产物。尽管烯胺酮酯通常耐金属氢化物还原，但一种无阻碍的烯胺酮酯可与硼氢化钠还原为醇。另一种烯胺酯与胍反应，得到相应的喹唑啉酮。由于烯胺酮系统中亲核和亲电子位点的多样性，烯胺酮酯具有作为反应中间体和药用化合物的巨大潜力。烯胺酮酯的初步评估显示了组胺能作用，子宫松弛特性和抗惊厥活性。

  DOI：

  10.1002/jps.2600830119
• 作为产物：
  描述：

  苄叉丙酮 、 丙二酸二甲酯 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 methyl 2-hydroxy-4-oxo-6-phenylcyclohex-2-en-1-oate
  参考文献：
  名称：

  烯胺酯的合成，反应和初步评价

  摘要：

  这项工作的目的是设计具有潜在医学特性的烯胺酯。β-羟基酮酯与伯或仲胺之间的反应分别产生仲或叔烯胺酯。在酸性，碱性和中性介质中测定烯胺酯的紫外光谱。与中性介质相比，该光谱在酸性介质中具有七色移。烯胺酯为各种反应提供了亲核和亲电子位点。因此，烯胺酮酯仅转化为烯胺酰胺和O-烷基化产物。尽管烯胺酮酯通常耐金属氢化物还原，但一种无阻碍的烯胺酮酯可与硼氢化钠还原为醇。另一种烯胺酯与胍反应，得到相应的喹唑啉酮。由于烯胺酮系统中亲核和亲电子位点的多样性，烯胺酮酯具有作为反应中间体和药用化合物的巨大潜力。烯胺酮酯的初步评估显示了组胺能作用，子宫松弛特性和抗惊厥活性。

  DOI：

  10.1002/jps.2600830119

文献信息

• Synthesis, neuronal activity and mechanisms of action of halogenated enaminones
  作者：Ivan O. Edafiogho、Mohamed G. Qaddoumi、Kethireddy V.V. Ananthalakshmi、Oludotun A. Phillips、Samuel B. Kombian

  DOI：10.1016/j.ejmech.2014.02.002

  日期：2014.4

  Due to the excellent anticonvulsant activity of previously synthesized halogenated enaminones, more disubstituted analogs were synthesized and evaluated in vitro. The new enaminones either had no effect, depressed, or enhanced population spike (PS) amplitude in the rat hippocampus in a concentration-dependent manner. Structure–activity relationship (SAR) analysis indicated that compounds 21 and 25

  由于先前合成的卤代烯胺酮具有出色的抗惊厥活性，因此合成了更多的双取代类似物并进行了体外评估。在大鼠海马中，新的烯胺酮要么没有作用，要么没有抑制，或者没有增强，但浓度依赖性。结构-活性关系（SAR）分析表明，化合物21和25（具有二溴取代基）是等价的，并且比化合物2（具有二氯取代基）更有效，其中化合物25是所有测试化合物中最有效的。二碘代衍生物30和31测试对PS没有产生显着影响。对于PS抑郁症，环己烯酮环上的苯基取代产生最有效的化合物25。压抑PS的类似物还压抑了诱发的兴奋性突触后电流（EPSC）和动作电位触发频率。从烯胺酯的环己烯酮环上的6位上除去苯基或甲基，制得显示出前惊厥作用的化合物28。C log P值与卤代烯胺酮的抗惊厥活性之间没有直接关系。抗惊厥活性的机制是通过增强细胞外GABA间接抑制兴奋性突触传递，以及直接抑制神经元动作电位的激发。
• Ultraviolet spectroscopy of anticonvulsant enaminones
  作者：I.O Edafiogho、O.A Phillips、M Abdel-Hamid、A.A.M Ali、W.C Matowe、A El-Hashim、S.B Kombian

  DOI：10.1016/s0968-0896(01)00314-5

  日期：2002.3

  The ultraviolet (UV) spectra of selected enaminones were determined in acidic, alkaline and neutral media and compared to their anticonvulsant activities. The wavelength of maximum absorption and molar absorptivity were compared with the anticonvulsant activity of the selected secondary and tertiary enaminones. and general inferences were made. The UV spectra of the enaminones had hypsochromic shifts in acidic media in comparison with neutral media. Generally, a small hypsochromic shift occurred in alkaline media when compared to the neutral solutions of the enaminones. The tertiary enaminones absorbed UV light at longer wavelength than the secondary enaminones in acidic, neutral and alkaline media. In particular, the tertiary enaminones displayed absorption at the higher end and secondary enaminones towards the lower end of the UV wavelength range 292-315 nm in aqueous media. Tertiary enaminones (30-33) which were devoid of the NH proton were found to be uniformly inactive in a mouse model of electroshock seizures, while some secondary enaminones (1, 5-8, 12. 16, 18, 20, 23-25, 28 and 29) had anticonvulsant activity. Thus the NH group of secondary enaminones is very important for anticonvulsant activity, and this agrees with an already established trend in proton NMR spectroscopy. In addition, the pares-substitution on the phenyl group in some enaminones result in higher molar absorptivity (a) values that enhance anticonvulsant activity. These results indicate that the anticonvulsant activity of enaminones is not due to electronic effect alone, but is probably due to a combination of factors including electronic and steric effects. lipophilicity, and hydrogen bonding. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis, antibacterial and anticonvulsant evaluations of some cyclic enaminones
  作者：Ivan O. Edafiogho、Oludotun A. Phillips、Edet E. Udo、Santosh Samuel、Beigy Rethish

  DOI：10.1016/j.ejmech.2008.07.005

  日期：2009.3

  Several cyclic enaminone esters were synthesized, characterized, and evaluated for anticonvulsant and antibacterial activities using standardized tests, A series of enaminones were mainly phenyl analogs of anticonvulsant enaminones, while a second series comprised of compounds bearing the oxazolidinone pharmacophoric moiety found in the synthetic antibacterial linezolid. The enaminone ester bearing an unsubstituted anilino analog showed class 2 anticonvulsant activity. This represents a first report of an unsubstituted anilino enaminone with anticonvulsant activity. The enaminone esters gave interesting UV data, and four analogs displayed potent anticonvulsant activities, while another four compounds showed moderate anticonvulsant activities. Surprisingly, none of the enaminone esters had any significant antibacterial activity. (C) 2008 Elsevier Masson SAS. All rights reserved.