9-bromo-5-tosyl-3,4,5,6-tetrahydro-1H-1,5-benzodiazonine-2,7-dione | 1268694-35-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 9-bromo-5-tosyl-3,4,5,6-tetrahydro-1H-1,5-benzodiazonine-2,7-dione
• 英文别名: 9-Bromo-5-(4-methylphenyl)sulfonyl-1,3,4,6-tetrahydro-1,5-benzodiazonine-2,7-dione；9-bromo-5-(4-methylphenyl)sulfonyl-1,3,4,6-tetrahydro-1,5-benzodiazonine-2,7-dione
• CAS: 1268694-35-4
• 化学式: C₁₈H₁₇BrN₂O₄S
• 分子量: 437.314
• InChiKey: KRXDGHMSFDPPJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  91.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 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 4.67h， 生成 9-bromo-5-tosyl-3,4,5,6-tetrahydro-1H-1,5-benzodiazonine-2,7-dione
  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

• 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.