4-chloro-8-nitro-3-chlorosulfonylquinoline | 1394122-02-1

• 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-chloro-8-nitro-3-chlorosulfonylquinoline
• CAS: 1394122-02-1
• 化学式: C₉H₄Cl₂N₂O₄S
• 分子量: 307.114
• InChiKey: NTNJOTCAOVDRSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  90.17
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-chloro-8-nitro-3-chlorosulfonylquinoline 、 二甲胺 以 水 、 苯 为溶剂， 反应 2.0h， 以90%的产率得到4-dimethylamino-8-nitro-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
• 作为产物：
  描述：

  1,11-dinitrothioquinanthrene 在 盐酸 、 氯 、 溶剂黄146 作用下， 以 氯仿 、 水 为溶剂， 反应 0.25h， 生成 4-chloro-8-nitro-3-chlorosulfonylquinoline 、 4-chloro-5-nitro-3-quinolinesulfonyl chloride
  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