4-dimethylamino-3-quinoline-N,N-dimethylsulfonamide | 157494-23-0

• 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: 4-dimethylamino-3-quinoline-N,N-dimethylsulfonamide
• 英文别名: 4-(dimethylamino)-N,N-dimethylquinoline-3-sulfonamide
• CAS: 157494-23-0
• 化学式: C₁₃H₁₇N₃O₂S
• 分子量: 279.363
• InChiKey: XPKOGDVDZHNPNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  61.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-dimethylamino-3-quinoline-N,N-dimethylsulfonamide 在 盐酸 作用下， 反应 3.0h， 以80%的产率得到4-Oxo-1,4-dihydro-quinoline-3-sulfonic acid dimethylamide
  参考文献：
  名称：

  Hydrolysis of 4-Amino-3-qunolinesulfonamides

  摘要：

  Acid hydrolysis of 4-amino-3-quinolinesulfonamides (3) gives 1,4-dihydro-4-oxo-3-quinolinesulfonamides (4), 4-aminoquinolines (5) or a mixture of these compounds.

  DOI：

  10.3987/com-98-8164
• 作为产物：
  描述：

  thioquinanthrene sulfoxide 在 盐酸 、 氯 、 溶剂黄146 作用下， 以 氯仿 、 水 、 苯 为溶剂， 反应 2.25h， 生成 4-dimethylamino-3-quinoline-N,N-dimethylsulfonamide
  参考文献：
  名称：

  Preparation and Oxidative-Chlorination Splitting of Nitro Derivatives OF 1,4-Dithiino[2,3-C:5,6-C′]Diquinoline as a Source of 4-Substituted 5- and 8-Nitro-3-Quinolinesulfonic Acid Derivatives

  摘要：

  Treatment of 1,4-dithiino[2,3-c:5,6-c']diquinoline (a thioquinanthrene) (1a) with an excess of nitrating mixture (0 degrees C, 14 days) led to a mixture of mono-and dinitrothioquinanthrene 7-oxides 2b-e and 2f-h. This mixture was: (i) reduced to a mixture of mono- and dinitrothioquinanthrenes 1b-e, or (ii) oxidatively chlorinated with a gaseous chlorine/80% acetic acid/hydrochloric acid system to a mixture of 4-chloro-3-chlorosulfonylquinoline 3a and its 5- and 8-nitroderivatives 3b and 3d. Sulfochlorides 3a-d were independently synthesized from 3,4'-diquinolinyl sulfides 4 and converted to the respective 4-dimethylamino-3-quinoline-N,N-dimethylsulfonamides 9a-d.

  DOI：

  10.1080/10426507.2012.680085

文献信息

• Synthesis and Amination of 4-Chloro-3-quinolinesulfonyl Chloride
  作者：Andrzej Maslankiewicz、Leszek Skrzypek

  DOI：10.3987/com-94-6683

  日期：——

  Chlorinolysis of 4-chloro-3-benzylthioquinoline (2) or thioquinanthrene (1) using chlorine gas in the presence of water gave 4-chloro-3-quinolinesulfonyl chloride (3). Amination of (3) performed in ether led to 4-chloro-3-quinolinesulfonamides (4). Reactions of compound (3) with an excess of primary or secondary amine in two phase (water/toluene or benzene) system gave 4-(substituted amino)-3-quinolinesulfonamides (5) with two identical amine rests. While 4-chloro-3-quinolinesulfonamides (4) were aminated with an excess of amine into aminosulfonamides (5) with two identical or two various amine rests.
• The Preparation of 1-Methyl- (and Ethyl)-1,4-dihydro-4-oxo- and 4-thioxo-3-quinolinesulfonamides from 4-Amino-3-quinolinesulfonamides
  作者：Leszek Skrzypek

  DOI：10.3987/com-99-8607

  日期：——
• Hydrolysis of 4-Amino-3-qunolinesulfonamides
  作者：Leszek Skrzypek

  DOI：10.3987/com-98-8164

  日期：——

  Acid hydrolysis of 4-amino-3-quinolinesulfonamides (3) gives 1,4-dihydro-4-oxo-3-quinolinesulfonamides (4), 4-aminoquinolines (5) or a mixture of these compounds.
• Preparation and Oxidative-Chlorination Splitting of Nitro Derivatives OF 1,4-Dithiino[2,3-C:5,6-C′]Diquinoline as a Source of 4-Substituted 5- and 8-Nitro-3-Quinolinesulfonic Acid Derivatives
  作者：Elwira Chrobak、Andrzej Maślankiewicz、Magdalena Chyćko、Leszek Skrzypek、Małgorzata Szmielew、Maria J. Maślankiewicz、Joachim Kusz、Maciej Zubko

  DOI：10.1080/10426507.2012.680085

  日期：2012.10.1

  Treatment of 1,4-dithiino[2,3-c:5,6-c']diquinoline (a thioquinanthrene) (1a) with an excess of nitrating mixture (0 degrees C, 14 days) led to a mixture of mono-and dinitrothioquinanthrene 7-oxides 2b-e and 2f-h. This mixture was: (i) reduced to a mixture of mono- and dinitrothioquinanthrenes 1b-e, or (ii) oxidatively chlorinated with a gaseous chlorine/80% acetic acid/hydrochloric acid system to a mixture of 4-chloro-3-chlorosulfonylquinoline 3a and its 5- and 8-nitroderivatives 3b and 3d. Sulfochlorides 3a-d were independently synthesized from 3,4'-diquinolinyl sulfides 4 and converted to the respective 4-dimethylamino-3-quinoline-N,N-dimethylsulfonamides 9a-d.