7,7-dimethyl-5-oxo-2-thioxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile | 303013-99-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 7,7-dimethyl-5-oxo-2-thioxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile
• 英文别名: 7,7-dimethyl-5-oxo-2-sulfanylidene-6,8-dihydro-1H-quinoline-3-carbonitrile
• CAS: 303013-99-2
• 化学式: C₁₂H₁₂N₂OS
• mdl: MFCD01541461
• 分子量: 232.306
• InChiKey: ZVBVJGPOTJDKCP-UHFFFAOYSA-N

物化性质

• 熔点：
  >300 °C(Solv: acetic acid (64-19-7); N,N-dimethylformamide (68-12-2))
• 沸点：
  346.8±52.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.416
• 拓扑面积：
  85
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  7,7-dimethyl-5-oxo-2-thioxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile 在 氢氧化钾 、 溴 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 12.5h， 生成 6-bromo-7,7-dimethyl-2-(methylsulfanyl)-5-oxo-5,6,7,8-tetrahydroquinoline-3-carbonitrile
  参考文献：
  名称：

  摘要：

  Simple methods for the synthesis of previously unknown sulfur-containing pyridia-2-ones and 5,6,7,8-tetrahydroquinolines from cyanothioacetamide and anilinomethylidene derivatives of cyclic 1,3-dicarbonyl compounds were developed. Structures and chemical transformations of compounds obtained were studied.

  DOI：

  10.1023/a:1020939712830
• 作为产物：
  描述：

  2-氰基硫代乙酰胺 、 2-dimethylaminomethylene-5,5-dimethylcyclohexane-1,3-dione 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 0.33h， 以83%的产率得到7,7-dimethyl-5-oxo-2-thioxo-1,2,5,6,7,8-hexahydroquinoline-3-carbonitrile
  参考文献：
  名称：

  烯胺酮在杂环合成中的构建基块：一种多官能取代的环己烯嗪的新方法

  摘要：

  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。

  DOI：

  10.1002/jhet.5570400421

文献信息

• Tetrahydroquinolinones and their use as antagonists of metabotropic glutamate receptors
  申请人：Jirgensons Aigars

  公开号：US20050197361A1

  公开（公告）日：2005-09-08

  The invention relates to tetrahydroquinolinone derivatives as well as their pharmaceutially acceptable salts. The invention further relates to a process for the preparation of such compounds. The compounds of the invention are group I mGluR antagonists and are therefore useful for the control and prevention of acute and/or chronic neurological disorders.

  该发明涉及四氢喹诺酮衍生物及其药用可接受的盐。该发明还涉及一种制备这种化合物的方法。该发明的化合物是I组mGluR拮抗剂，因此对于控制和预防急性和/或慢性神经系统疾病非常有用。
• Positive and Negative Modulation of Group I Metabotropic Glutamate Receptors
  作者：Maksims Vanejevs、Claudia Jatzke、Steffen Renner、Sibylle Müller、Mirko Hechenberger、Tanja Bauer、Anna Klochkova、Ilya Pyatkin、Denis Kazyulkin、Elena Aksenova、Sergey Shulepin、Olga Timonina、Ariane Haasis、Aleksandrs Gutcaits、Christopher G. Parsons、Valerjans Kauss、Tanja Weil

  DOI：10.1021/jm0611298

  日期：2008.2.1

  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.
• TETRAHYDROQUINOLINONES AND THEIR USE AS ANTAGONISTS OF METABOTROPIC GLUTAMATE RECEPTORS
  申请人：Merz Pharma GmbH & Co. KGaA

  公开号：EP1723116A2

  公开（公告）日：2006-11-22
• US7598384B2
  申请人：——

  公开号：US7598384B2

  公开（公告）日：2009-10-06
• [EN] TETRAHYDROQUINOLINONES AND THEIR USE AS ANTAGONISTS OF METABOTROPIC GLUTAMATE RECEPTORS<br/>[FR] TETRAHYDROQUINOLINONES ET LEUR UTILISATION COMME ANTAGONISTES DES RECEPTEURS DE GLUTAMATE METABOTROPIQUE
  申请人：MERZ PHARMA GMBH & CO KGAA

  公开号：WO2005082856A2

  公开（公告）日：2005-09-09

  The invention relates to tetrahydroquinolinone derivatives as well as their pharmaceutically acceptable salts. The invention further relates to a process for the preparation of such compounds. The compounds of the invention are group I mGluR antagonists and are therefore useful for the control and prevention of acute and/or chronic neurological disorders.