methyl 2-hydroxy-6,6-dimethyl-4-oxocyclohex-2-en-1-oate | 70328-68-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-hydroxy-6,6-dimethyl-4-oxocyclohex-2-en-1-oate
• 英文别名: Methyl 2,2-dimethyl-4,6-dioxacyclohexane-1-carboxylate；methyl 4-hydroxy-6,6-dimethyl-2-oxocyclohex-3-ene-1-carboxylate
• CAS: 70328-68-6
• 化学式: C₁₀H₁₄O₄
• 分子量: 198.219
• InChiKey: RNWSGTDZTJYKTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.22
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 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-6,6-dimethyl-4-oxocyclohex-2-en-1-oate 在 氨 作用下， 以 甲苯 为溶剂， 反应 40.0h， 生成 6,6-dimethyl-2-oxo-4-pyrrolidinocyclohex-3-enecarboxamide
  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：

  4-甲基-3戊烯-2-酮 、 丙二酸二甲酯 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 methyl 2-hydroxy-6,6-dimethyl-4-oxocyclohex-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 of Tetra- and Pentasubstituted Benzenes from Dimedone and Derivatives
  作者：Peter H. Nelson、Janis T. Nelson

  DOI：10.1055/s-1992-26360

  日期：——

  Treatment of dimedone (5,5-dimethylcyclohexane-1,3-dione) and derivatives with one molar equivalent of sulfuric acid in trifluoroacetic anhydride leads, via sulfonation and a 1,2-methyl group migration, to a variety of dimethylresorcinol derivatives. The reaction has been performed on substrates bearing ester, alkoxy, halo and amino substituents to produce a variety of polysubstituted benzenes. Transient sulfonated intermediates were observed by NMR.

  对二美噻（5,5-二甲基环己烷-1,3-二酮）及其衍生物与一摩尔当量的硫酸在三氟乙酸酐中反应，通过磺化和1,2-甲基基团迁移，可以生成多种二甲基水杨醇衍生物。该反应已在带有酯、醚、卤素和氨基取代基的底物上进行，以生成多种多取代苯。通过核磁共振（NMR）观察到了暂态磺化中间体。
• [DE] CYCLOHEXENONOXIMETHER-METALLSALZE<br/>[EN] CYCLOHEXENONE OXIME ETHER METAL SALTS<br/>[FR] SELS METALLIQUES D'ETHER D'OXIME DE CYCLOHEXENONE
  申请人：BASF AKTIENGESELLSCHAFT

  公开号：WO1997020807A1

  公开（公告）日：1997-06-12

  (DE) Die Erfindung betrifft herbizid wirksame Cyclohexenonoximether-Metallsalze der Formel (I), wobei Rn = C1-Cn-Alkyl und Rb = das Äquivalent eines Alkali-, Erdalkali- oder Übergangsmetalles bedeuten. Die beanspruchten Salze besitzen besonders gute Eigenschaften im Hinblick auf Lager- und Temperaturstabilität, Anfälligkeit gegen Feuchtigkeit oder biologische Wirkung.(EN) The invention relates to herbicidally active cyclohexenone oxime ether metal salts of formula (I), in which Rn is C1-Cn-alkyl and Rb is the equivalent of an alkali metal, an alkaline earth metal or a transition metal. The claimed salts have particularly good properties with respect to storage stability and temperature stability, susceptibility to moisture or biological action.(FR) L'invention concerne des sels métalliques d'éther d'oxime de cyclohéxénone de formule (I), ayant un effet herbicide. Dans la formule, Rn est alkyle C1-Cn et Rb est l'équivalent d'un métal alcalin, d'un métal alcalino-terreux ou d'un métal de transition. Les sels revendiqués possèdent d'excellentes propriétés sur le plan de la stabilité au stockage et de la stabilité thermique, de la sensibilité à l'humidité ou de l'action biologique.

  该发明涉及一种 herbicidally effective cyclohexenonoximether-metal salt of formula (I)，其中 Rn是 C1-Cn-alkyl，而 Rb 是碱金属的相应当量、碱性地壳金属的相应当量或过渡金属的相应当量。这些 claimed salts 具有特别好的特性，以存储稳定性和温度稳定性、对湿度或生物作用的敏感性为焦点。
• Anticonvulsant evaluation and mechanism of action of benzylamino enaminones
  作者：Ivan O. Edafiogho、Kethireddy V.V. Ananthalakshmi、Samuel B. Kombian

  DOI：10.1016/j.bmc.2006.03.049

  日期：2006.8

  The mechanism of anticonvulsant action was evaluated for the benzylamino enaminones. The most potent enaminone in this series was the unsubstituted benzylamine analog (30; methyl 4-benzylamino-6-methyl-2-oxocyclohex-3-en-1-oate) which had an oral effective dose (EDSO) in rats of 27 mg/kg against maximal electroshock seizures, and a concentration 10-fold less than this dose depressed excitatory synaptic transmission, and action potential firing in the rat brain in vitro. (c) 2006 Elsevier Ltd. All rights reserved.
• 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.
• CYCLOHEXENONOXIMETHER-METALLSALZE
  申请人：BASF AKTIENGESELLSCHAFT

  公开号：EP0871609A1

  公开（公告）日：1998-10-21