7-bromo-1H-pyrrolo[3,2-b]quinolin-9(4H)-one | 1188269-86-4

• 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: 7-bromo-1H-pyrrolo[3,2-b]quinolin-9(4H)-one
• 英文别名: 7-Bromo-1,4-dihydropyrrolo[3,2-b]quinolin-9-one；7-bromo-1,4-dihydropyrrolo[3,2-b]quinolin-9-one
• CAS: 1188269-86-4
• 化学式: C₁₁H₇BrN₂O
• 分子量: 263.093
• InChiKey: NFYHEWNRIQWWET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  44.9
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-bromo-1H-pyrrolo[3,2-b]quinolin-9(4H)-one 在 N-溴代丁二酰亚胺(NBS) 、 溶剂黄146 作用下， 反应 1.0h， 以87%的产率得到3,7-dibromo-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-溴苯肼盐酸盐 在 臭氧 、 溶剂黄146 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.83h， 生成 7-bromo-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

文献信息

• Polystyrene Sulfonyl Chloride: A Highly Orthogonal Linker Resin for the Synthesis of Nitrogen-Containing Heterocycles
  作者：Matthias Mentel、Axel M. Schmidt、Michael Gorray、Peter Eilbracht、Rolf Breinbauer

  DOI：10.1002/anie.200901643

  日期：2009.7.27

  One linker, broad application: A simple sulfonamide linker for primary and secondary amines was used for the construction of small libraries of privileged indole and quinolone structures on a solid phase. After the synthesis, the products can be liberated ion a traceless manner under electron transfer conditions or according to a “safety catch” principle.

  一个接头，广泛应用：用于伯胺和仲胺的简单磺酰胺接头用于在固相上构建具有特权吲哚和喹诺酮结构的小型文库。合成后，可以在电子转移条件下或根据“安全捕获”原理以无痕迹的方式释放产物。
• The Witkop–Winterfeldt oxidation converts tetrahydropyridoindoles into pyrroloquinolones and cinnolines by an unprecedented scaffold rearrangement
  作者：Matthias Mentel、Martin Peters、Jörg Albering、Rolf Breinbauer

  DOI：10.1016/j.tet.2010.11.110

  日期：2011.2

  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.