7,7-dimethyl-2,5-dioxo-1,2,5,6,7,8-hexahydro-quinoline-3-carbonitrile | 51369-19-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 7,7-dimethyl-2,5-dioxo-1,2,5,6,7,8-hexahydro-quinoline-3-carbonitrile
• 英文别名: 7,7-dimethyl-2,5-dioxo-1,2,5,6,7,8-hexahydro-3-quinolinecarbonitrile；7,7-dimethyl-2,5-dioxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile；7,7-dimethyl-2,5-dioxo-6,8-dihydro-1H-quinoline-3-carbonitrile
• CAS: 51369-19-8
• 化学式: C₁₂H₁₂N₂O₂
• 分子量: 216.239
• InChiKey: XRYRWQJSUJBOAB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  70
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7,7-dimethyl-2,5-dioxo-1,2,5,6,7,8-hexahydro-quinoline-3-carbonitrile 在 三氯氧磷 作用下， 反应 5.0h， 以46%的产率得到2-chloro-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-quinoline-3-carbonitrile
  参考文献：
  名称：

  Positive and Negative Modulation of Group I Metabotropic Glutamate Receptors

  摘要：

  A discriminating pharmacophore model for noncompetitive metabotropic glutamate receptor antagonists of subtype 1 (mGluR1) was developed that facilitated the discovery of moderately active mGluR1 antagonists. One scaffold was selected for the design of several focused libraries where different substitution patterns were introduced. This approach facilitated the discovery of potent mGluR1 antagonists, as well as positive and negative mGluR5 modulators, because both receptor subtypes share similar binding pockets. For mGluR1 antagonists, a homology model of the mGlu1 receptor was established and a putative binding mode within the receptor's transmembrane domain was visualized.

  DOI：

  10.1021/jm0611298
• 作为产物：
  描述：

  2-dimethylaminomethylene-5,5-dimethylcyclohexane-1,3-dione 在 溶剂黄146 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 72.0h， 生成 7,7-dimethyl-2,5-dioxo-1,2,5,6,7,8-hexahydro-quinoline-3-carbonitrile
  参考文献：
  名称：

  Fossa; Boggia; Lo Presti, Il Farmaco, 1997, vol. 52, # 8-9, p. 523 - 530

  摘要：

  DOI：

文献信息

• Enaminones as building blocks in heterocyclic syntheses: A new approach to polyfunctionally substituted cyclohexenoazines
  作者：Saleh Al-Mousawi、Elizabeth John、Mervat Mohammed Abdelkhalik、Mohammed Hilmy Elnagdi

  DOI：10.1002/jhet.5570400421

  日期：2003.7

  A variety of polyfunctionally substituted condensed pyridines and pyrazolotetrahydroquinazolines have been synthesized utilizing cyclic enaminones as starting materials.

  利用环状烯胺酮作为起始原料合成了多种多官能取代的稠合吡啶和吡唑并四氢喹唑啉。
• Synthesis of functionally substituted derivatives of thiazolo[4,5-f]quinoline, pyridazino[3,4-f] quinoline and 5-hydroxyquinoline based on 3-cyano-6-bromo-1,2,5,6,7,8-hexahydroquinoline-2,5-dione
  作者：V. A. Azimov、N. P. Solov'eva、V. G. Granik

  DOI：10.1007/bf02219036

  日期：1994.8

  interphase catalyst, triethylbenzylammonium chloride (TEBAC). Under these conditions, however, the reaction proceeded mainly in the direction of dehydrobromination and formation of 3-cyano-5-hydroxy-2-quinoline (VII) in 68% yield. The desired product, 3-cyano-6(diethoxycarbonyl)methyl-l,2,5,6,7~8-hexahydroquinoline-2,5-dione, was isolated in a yield of only 10%. Reaction of this compound with hydrazine hydrate

  最近，文献中出现了关于噻唑并 [4,5-f] 喹啉衍生物显着强心活性的数据 [1]。在合成具有强心活性的 3-cyano-2-pyridone 系列衍生物的研究过程中 [2]，在目前的工作中，我们进行了基于反应的噻唑并 [4,5-f] 喹啉系列成员的合成在 [1] 和 3-cyano-6-bromo1,2,5,6,7,8-hexahydroquinoline-215-dione (I) 与不同硫代酰胺的反应中开发。对于后者，我们选择了硫氰乙酰胺 (II) 和内酰胺衍生物：1-硫代氨基甲酰基甲基 I-2-吡咯烷酮 (IIIa)、-硫代-2 吡咯烷酮 (IIIb) 和 -己内酰胺 (IIIc)，通过用 NH4HS 处理相应的 N-氰基甲基内酰胺获得[3]，或（在 IIIb 的情况下）通过使吡拉西坦 1-氨基甲酰基-2-吡咯烷酮与五硫化二磷反应 [4]。在尝试重现获得溴代衍生物 I [1] 的已知方法时，我们遇到了重大困难：通过
• Rapid microwave-assisted solution phase synthesis of substituted 2-pyridone libraries
  作者：Nikolay Yu. Gorobets、Behrooz H. Yousefi、Ferdinand Belaj、C.Oliver Kappe

  DOI：10.1016/j.tet.2004.05.100

  日期：2004.9

  2-Pyridone and 2-quinolone analogues are well-known biologically active heterocyclic scaffolds. Libraries of 3,5,6-substituted 2-pyridone derivatives are generated by rapid microwave assisted solution phase methods using a one-pot, two-step protocol. The three-component condensation of CH-acidic carbonyl compounds, NN-dimethylformamide dimethylacetal and methylene active nitriles, leads to 2-pyridones and fused analogues in moderate to good overall yields and high purities. The proposed mechanism of this novel multicomponent reaction, structure elucidation of products and intermediates are discussed. (C) 2004 Elsevier Ltd. All rights reserved.
• Mosti, Luisa; Schenone, Pietro; Menozzi, Giulia, Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 1503 - 1509
  作者：Mosti, Luisa、Schenone, Pietro、Menozzi, Giulia

  DOI：——

  日期：——
• GUDRINIETSE, EH. YU.;PAXUROVA, T. F.;LIEPINSH, EH. EH., ZH. ORGAN. XIMII, 1982, 18, N 11, 2361-2363
  作者：GUDRINIETSE, EH. YU.、PAXUROVA, T. F.、LIEPINSH, EH. EH.

  DOI：——

  日期：——