1-tosyl-2,3-dihydro-1H-pyrrolo[3,2-b]quinolin-9(4H)-one | 1268694-36-5

• 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: 1-tosyl-2,3-dihydro-1H-pyrrolo[3,2-b]quinolin-9(4H)-one
• 英文别名: 1-(4-methylphenyl)sulfonyl-3,4-dihydro-2H-pyrrolo[3,2-b]quinolin-9-one
• CAS: 1268694-36-5
• 化学式: C₁₈H₁₆N₂O₃S
• 分子量: 340.403
• InChiKey: IRUNYSPVOKXPPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  74.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-tosyl-2,3-dihydro-1H-pyrrolo[3,2-b]quinolin-9(4H)-one 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以100%的产率得到1H-pyrrolo[3,2-b]quinolin-9(4H)-one
  参考文献：
  名称：

  The Witkop–Winterfeldt oxidation converts tetrahydropyridoindoles into pyrroloquinolones and cinnolines by an unprecedented scaffold rearrangement

  摘要：

  The Fischer indole reaction between phenylhydrazines and tosyl-4-piperidone furnishes tetrahydropyrido[4,3-b]indoles. In a Witkop-Winterfeldt-oxidation using ozone such indole derivatives are converted into medium-sized dicarbonyl ring systems, which cyclize to pyrroloquinolones. A detailed study of the reaction intermediates and the characterization of a cinnoline betaine side product formed by an unprecedented ring closure mechanism are reported. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.11.110
• 作为产物：
  描述：

  4-哌啶酮，1-[（4-甲基苯基）磺酰基]- 在 臭氧 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 24.83h， 生成 1-tosyl-2,3-dihydro-1H-pyrrolo[3,2-b]quinolin-9(4H)-one
  参考文献：
  名称：

  The Witkop–Winterfeldt oxidation converts tetrahydropyridoindoles into pyrroloquinolones and cinnolines by an unprecedented scaffold rearrangement

  摘要：

  The Fischer indole reaction between phenylhydrazines and tosyl-4-piperidone furnishes tetrahydropyrido[4,3-b]indoles. In a Witkop-Winterfeldt-oxidation using ozone such indole derivatives are converted into medium-sized dicarbonyl ring systems, which cyclize to pyrroloquinolones. A detailed study of the reaction intermediates and the characterization of a cinnoline betaine side product formed by an unprecedented ring closure mechanism are reported. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.11.110