4-Chloro-quinoline-3-sulfonic acid methyl-phenyl-amide | 157494-18-3

• 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-quinoline-3-sulfonic acid methyl-phenyl-amide
• 英文别名: 4-chloro-N-methyl-N-phenylquinoline-3-sulfonamide
• CAS: 157494-18-3
• 化学式: C₁₆H₁₃ClN₂O₂S
• 分子量: 332.81
• InChiKey: BUCYPBSGSYYISQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  58.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-Chloro-quinoline-3-sulfonic acid methyl-phenyl-amide 在 sodium hydroxide 、 sodium hydrogensulfide 、 双氧水 作用下， 以 乙醇 为溶剂， 反应 24.5h， 生成 1,4-dihydro-4-oxo-N-methyl-3-quinolinesulfonanilide
  参考文献：
  名称：

  A Synthesis and Reactivity of 1,4-Dihydro-4-thioxo-3-quinolinesulfonamides

  摘要：

  4-Chloro-3-quinolinesulfonamides (1) were transformed to 1,4-dihydro-4-thioxo-3-quinolinesulfonamides (2) which methylation gave 4-methylthio-3-quinolinesulfonamides (3). Oxidation of sulfonamides (2) with hydrogen peroxide provided 1,4-dihydro-4-oxo-3-quinolinesulfonamides (4).

  DOI：

  10.3987/com-04-10270
• 作为产物：
  描述：

  1,4-dithiino[2,3-c:5,6-c']diquinoline 在 氯 、 溶剂黄146 作用下， 以 乙醚 、 氯仿 、 水 为溶剂， 反应 2.0h， 生成 4-Chloro-quinoline-3-sulfonic acid methyl-phenyl-amide
  参考文献：
  名称：

  Synthesis and Amination of 4-Chloro-3-quinolinesulfonyl Chloride

  摘要：

  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.

  DOI：

  10.3987/com-94-6683

文献信息

• The Preparation of 1-Nonsubstituted and 1-Methyl- (and Ethyl)-1,4-dihydro-4-oxo- 3-quinolinesulfonamides from 4-Chloro-3-quinolinesulfonamides
  作者：Andrzej Maslankiewicz、Leszek Skrzypek

  DOI：10.3987/com-97-7887

  日期：——
• Malankiewicz Andrzej, Skrzypek Leszek, Heterocycles, 38 (1994) N 6, S 1317-1331
  作者：Malankiewicz Andrzej, Skrzypek Leszek

  DOI：——

  日期：——
• 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.
• A Synthesis and Reactivity of 1,4-Dihydro-4-thioxo-3-quinolinesulfonamides
  作者：Leszek Skrzypek

  DOI：10.3987/com-04-10270

  日期：——

  4-Chloro-3-quinolinesulfonamides (1) were transformed to 1,4-dihydro-4-thioxo-3-quinolinesulfonamides (2) which methylation gave 4-methylthio-3-quinolinesulfonamides (3). Oxidation of sulfonamides (2) with hydrogen peroxide provided 1,4-dihydro-4-oxo-3-quinolinesulfonamides (4).