14-methyl-1,2-dihydroquinolino[2',3':3,4]-pyrrolo[2,1-b]quinazoline-5,8(13H)-dione | 1316852-09-1

• 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: 14-methyl-1,2-dihydroquinolino[2',3':3,4]-pyrrolo[2,1-b]quinazoline-5,8(13H)-dione
• 英文别名: 3-Methyl-3,11,21-triazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(13),4,6,8,15,17,19-heptaene-10,14-dione
• CAS: 1316852-09-1
• 化学式: C₁₉H₁₅N₃O₂
• 分子量: 317.347
• InChiKey: ATFVFDCSDINFBG-UHFFFAOYSA-N

物化性质

• 熔点：
  240 °C (decomp)
• 沸点：
  573.3±50.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  52.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  14-methyl-1,2-dihydroquinolino[2',3':3,4]-pyrrolo[2,1-b]quinazoline-5,8(13H)-dione 在 氯化亚砜 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以72%的产率得到8-chloro-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
• 作为产物：
  描述：

  吴茱萸碱 在 potassium tert-butylate 、 氧气 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 以48%的产率得到14-methyl-1,2-dihydroquinolino[2',3':3,4]-pyrrolo[2,1-b]quinazoline-5,8(13H)-dione
  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

文献信息

• Intramolecular N-aza-amidoalkylation in association with Witkop–Winterfeldt oxidation as the key step to synthesize Luotonin-A analogues
  作者：Frédéric Pin、Sébastien Comesse、Adam Daïch

  DOI：10.1016/j.tet.2011.05.120

  日期：2011.8

  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.