methyl 4-(2-bromophenyl)benzo[c][2,7]naphthyridine-5-carboxylate | 1469803-49-3

• 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: methyl 4-(2-bromophenyl)benzo[c][2,7]naphthyridine-5-carboxylate
• 英文别名: Methyl 4-(2-bromophenyl)benzo[c][2,7]naphthyridine-5-carboxylate
• CAS: 1469803-49-3
• 化学式: C₂₀H₁₃BrN₂O₂
• 分子量: 393.239
• InChiKey: MBCYFLLBPKYXKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  52.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-(2-bromophenyl)benzo[c][2,7]naphthyridine-5-carboxylate 在 三氟甲磺酸 作用下， 反应 1.0h， 以46%的产率得到4-(2-bromophenyl)benzo[c][2,7]naphthyridine
  参考文献：
  名称：

  A novel approach to ring A analogues of the marine pyridoacridine alkaloid ascididemin

  摘要：

  A novel approach to ring A analogues of the marine pyridoacridine alkaloid ascididemin starting from readily available 4-bromobenzo[c][2,7]naphthyridine (10) comprises a high-yield Minisci-type homolytic methoxycarbonylation at C-5, followed by introduction of the ring A scaffold via Suzuki cross-coupling reaction, and a trifluoromethanesulfonic acid-aided Friedel-Crafts-type intramolecular acylation. This protocol allows for the introduction of various electron-rich carbocyclic and heterocyclic ring A substitutes. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.08.085
• 作为产物：
  描述：

  4-bromobenzo[c][2,7]naphthyridine 在 manganese(IV) oxide 、 四(三苯基膦)钯 、 硫酸 、 双氧水 、 potassium carbonate 作用下， 反应 12.0h， 生成 methyl 4-(2-bromophenyl)benzo[c][2,7]naphthyridine-5-carboxylate
  参考文献：
  名称：

  A novel approach to ring A analogues of the marine pyridoacridine alkaloid ascididemin

  摘要：

  A novel approach to ring A analogues of the marine pyridoacridine alkaloid ascididemin starting from readily available 4-bromobenzo[c][2,7]naphthyridine (10) comprises a high-yield Minisci-type homolytic methoxycarbonylation at C-5, followed by introduction of the ring A scaffold via Suzuki cross-coupling reaction, and a trifluoromethanesulfonic acid-aided Friedel-Crafts-type intramolecular acylation. This protocol allows for the introduction of various electron-rich carbocyclic and heterocyclic ring A substitutes. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.08.085

文献信息

• A novel approach to ring A analogues of the marine pyridoacridine alkaloid ascididemin
  作者：Alois Plodek、Stephan Raeder、Franz Bracher

  DOI：10.1016/j.tet.2013.08.085

  日期：2013.11

  A novel approach to ring A analogues of the marine pyridoacridine alkaloid ascididemin starting from readily available 4-bromobenzo[c][2,7]naphthyridine (10) comprises a high-yield Minisci-type homolytic methoxycarbonylation at C-5, followed by introduction of the ring A scaffold via Suzuki cross-coupling reaction, and a trifluoromethanesulfonic acid-aided Friedel-Crafts-type intramolecular acylation. This protocol allows for the introduction of various electron-rich carbocyclic and heterocyclic ring A substitutes. (C) 2013 Elsevier Ltd. All rights reserved.