2-(dimethylaminomethylidene)-5-methylcyclohexane-1,3-dione | 106551-63-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 乙烯基酰胺
• 英文名称: 2-(dimethylaminomethylidene)-5-methylcyclohexane-1,3-dione
• 英文别名: 2-((dimethylamino)methylene)-5-methylcyclohexane-1,3-dione
• CAS: 106551-63-7
• 化学式: C₁₀H₁₅NO₂
• 分子量: 181.235
• InChiKey: MYBHPGGKRQVRKK-VURMDHGXSA-N

物化性质

• 沸点：
  281.9±40.0 °C(Predicted)
• 密度：
  1.129±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.0
• 重原子数：
  13.0
• 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：
  37.38
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(dimethylaminomethylidene)-5-methylcyclohexane-1,3-dione 在 盐酸 、 铜 作用下， 以 喹啉 、 乙醇 为溶剂， 反应 165.25h， 生成 7-Methyl-7,8-dihydro-2,5-(1H,6H)-quinolinedione
  参考文献：
  名称：

  Mosti, Luisa; Schenone, Pietro; Menozzi, Giulia, Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 1503 - 1509

  摘要：

  DOI：
• 作为产物：
  描述：

  5-甲基环己烷-1,3-二酮 、 N,N-二甲基甲酰胺二甲基缩醛 以 乙酸乙酯 为溶剂， 以84%的产率得到2-(dimethylaminomethylidene)-5-methylcyclohexane-1,3-dione
  参考文献：
  名称：

  [EN] METABOTROPIC GLUTAMATE RECEPTOR MODULATORS
  [FR] MODULATEURS DES RÉCEPTEURS GLUTAMATERGIQUES MÉTABOTROPES

  摘要：

  这项发明涉及杂环衍生物及其药用可接受的盐。该发明还涉及一种制备这类化合物的方法。该发明的化合物是mGluR5调节剂，因此对于控制和预防急性和/或慢性神经系统疾病是有用的。

  公开号：

  WO2012085166A1

文献信息

• Lewis-Acid-Catalyzed Regioselective Construction of Diversely Functionalized Polycyclic Fused Furans
  作者：Sana Jamshaid、Yong Rok Lee

  DOI：10.1021/acs.orglett.2c00019

  日期：2022.2.18

  A novel, facile, and efficient Lewis-acid-catalyzed [4 + 1] annulation protocol for the construction of functionalized polycyclic-fused furans is developed. This methodology is free of transition metals and ligands and provides a rapid synthetic route to divergently orientated polycyclic furans in good yields. In addition, this protocol can also be used to synthesize multisubstituted furans.

  开发了一种用于构建功能化多环稠合呋喃的新型、简便且高效的路易斯酸催化 [4 + 1] 环化方案。该方法不含过渡金属和配体，并提供了一种快速合成途径，以良好的收率获得发散取向的多环呋喃。此外，该协议还可用于合成多取代呋喃。
• Fossa; Boggia; Lo Presti, Il Farmaco, 1997, vol. 52, # 8-9, p. 523 - 530
  作者：Fossa、Boggia、Lo Presti、Mosti、Dorigo、Floreani

  DOI：——

  日期：——
• Discovery, synthesis, and structure–activity relationships of 2-aminoquinazoline derivatives as a novel class of metabotropic glutamate receptor 5 negative allosteric modulators
  作者：Holger Kubas、Udo Meyer、Bjoern Krueger、Mirko Hechenberger、Maksims Vanejevs、Ronalds Zemribo、Valerjans Kauss、Raisa Ambartsumova、Ilya Pyatkin、Alexey I. Polosukhin、Ulrich Abel

  DOI：10.1016/j.bmcl.2013.06.049

  日期：2013.8

  A virtual screening approach using various in silico methodologies led to the discovery of 2-(m-tolylamino)-7,8-dihydroquinazolin-5(6H)-one (1) as a moderately active negative allosteric modulator (NAM) of the metabotropic glutamate receptor subtype 5 (mGluR5) showing high selectivity against the subtype mGluR1. Modifications of the parent compound by rational design yielded a series of highly potent derivatives which will serve as valuable starting points for further hit-to-lead optimization efforts toward a suitable drug candidate for the treatment of L-DOPA induced dyskinesia. (c) 2013 Elsevier Ltd. All rights reserved.
• Mosti; Menozzi; Schenone, Il Farmaco, 1994, vol. 49, # 1, p. 45 - 50
  作者：Mosti、Menozzi、Schenone、D'Amico、Falciani、Rossi

  DOI：——

  日期：——
• 3-Acetyl-5-acylpyridin-2(1H)-ones and 3-acetyl-7,8-dihydro-2,5(1H,6H)-quinolinediones: synthesis, cardiotonic activity and computational studies
  作者：Eleonora Lo Presti、Raffaella Boggia、Antonio Feltrin、Giulia Menozzi、Paola Dorigo、Luisa Mosti

  DOI：10.1016/s0014-827x(99)00053-1

  日期：1999.7

  A series of milrinone analogues, namely 6-substituted 3-acetyl-5-acylpyridin-2(1H)-ones 4a-c, e, f and 7-substituted or unsubstituted 3-acetyl-7,8-dihydro-2,5(1H,6H)-quinolinediones 4g-j, in which the cyano group was replaced by the acetyl function, was prepared. In a preliminary pharmacological investigation on spontaneously beating atria from reserpine-treated guinea-pigs, all new compounds did not induce any inotropic effect equivalent or higher than that of the milrinone chosen as the reference compound. In order to rationalise how the structure modifications influence the activity and the selectivity of the title compounds, a computational study has been performed. The important role of the substituents in position-3 and -6 on the pyridone nucleus has been highlighted. (C) 1999 Elsevier Science S.A. All rights reserved.