8-acetyloxy-14-methyl-1,2-dihydroquinolino-[2',3':3,4]pyrrolo[2,1-b]quinazolin-5-one | 1316852-12-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 8-acetyloxy-14-methyl-1,2-dihydroquinolino-[2',3':3,4]pyrrolo[2,1-b]quinazolin-5-one
• 英文别名: (3-Methyl-10-oxo-3,11,21-triazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),4,6,8,13,15,17,19-octaen-14-yl) acetate
• CAS: 1316852-12-6
• 化学式: C₂₁H₁₇N₃O₃
• 分子量: 359.384
• InChiKey: WKQDYDHXYBUJJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  62.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  吗啉 、 8-acetyloxy-14-methyl-1,2-dihydroquinolino-[2',3':3,4]pyrrolo[2,1-b]quinazolin-5-one 以 甲苯 为溶剂， 反应 48.0h， 以44%的产率得到8-morpholino-14-methyl-1,2-dihydroquinol-ino[2',3':3,4]pyrrolo[2,1-b]quinazolin-5-one
  参考文献：
  名称：

  Intramolecular N-aza-amidoalkylation in association with Witkop–Winterfeldt oxidation as the key step to synthesize Luotonin-A analogues

  摘要：

  An expedient four-step approach for the synthesis of a short library of original analogues of the Topo-I Luotonin-A inhibitor, substituted at their C-8- and N-15-positions, was investigated. This consists of Rutaecarpines formation, their Witkop-Winterfeldt oxidation followed ultimately with functional adjustment of the pyrroloquinolone intermediates. In the first step of these investigations. Rutaecarpines including the Topo-I poison Evodiamine were obtained via the new tandem N-acylation/aza-amidoalkylation using a nitrogen atom as an internal nucleophile with or without association with a decarboxylation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.120
• 作为产物：
  描述：

  吴茱萸碱 在 4-二甲氨基吡啶 、 potassium tert-butylate 、 氧气 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 8-acetyloxy-14-methyl-1,2-dihydroquinolino-[2',3':3,4]pyrrolo[2,1-b]quinazolin-5-one
  参考文献：
  名称：

  Intramolecular N-aza-amidoalkylation in association with Witkop–Winterfeldt oxidation as the key step to synthesize Luotonin-A analogues

  摘要：

  An expedient four-step approach for the synthesis of a short library of original analogues of the Topo-I Luotonin-A inhibitor, substituted at their C-8- and N-15-positions, was investigated. This consists of Rutaecarpines formation, their Witkop-Winterfeldt oxidation followed ultimately with functional adjustment of the pyrroloquinolone intermediates. In the first step of these investigations. Rutaecarpines including the Topo-I poison Evodiamine were obtained via the new tandem N-acylation/aza-amidoalkylation using a nitrogen atom as an internal nucleophile with or without association with a decarboxylation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.120