1-[5-(1,3,5-trioxan-2-yl)-5,6-dihydrobenzo[c][2,7]naphthyridin-4-yl]ethanone | 1380406-58-5

• 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: 1-[5-(1,3,5-trioxan-2-yl)-5,6-dihydrobenzo[c][2,7]naphthyridin-4-yl]ethanone
• CAS: 1380406-58-5
• 化学式: C₁₇H₁₆N₂O₄
• 分子量: 312.325
• InChiKey: XKEOFBWMBBYSFS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.72
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  69.68
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-[5-(1,3,5-trioxan-2-yl)-5,6-dihydrobenzo[c][2,7]naphthyridin-4-yl]ethanone 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 0.42h， 以91%的产率得到1-[5-(1,3,5-trioxan-2-yl)-benzo[c][2,7]naphthyridin-4-yl]ethanone
  参考文献：
  名称：

  Regioselective homolytic substitution of benzo[c][2,7]naphthyridines

  摘要：

  Benzo[c][2,7]naphthyridines bearing electron-withdrawing substituents (bromo, acetyl) at C-4 undergo regioselective homolytic substitutions at C-5 with nucleophilic 1,3,5-trioxanyl and ethoxycarbonyl radicals under Minisci conditions. Surprisingly, mainly 5,6-dihydro derivatives are formed in these reactions. Rearomatization with manganese dioxide leads to 4,5-disubstituted benzo[c][2,7]naphthyridines, which should be attractive building blocks for the synthesis of pyridoacridine alkaloids. Homolytic methylation at C-5 takes place with methyl radicals generated from acetic acid and acetaldehyde, respectively. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.023
• 作为产物：
  描述：

  三聚甲醛 、 1-(benzo[c][2,7]naphthyridin-4-yl)ethanone 在 双氧水 、 ferrous(II) sulfate heptahydrate 、 硫酸 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 2.25h， 以27%的产率得到1-[5-(1,3,5-trioxan-2-yl)-5,6-dihydrobenzo[c][2,7]naphthyridin-4-yl]ethanone
  参考文献：
  名称：

  Regioselective homolytic substitution of benzo[c][2,7]naphthyridines

  摘要：

  Benzo[c][2,7]naphthyridines bearing electron-withdrawing substituents (bromo, acetyl) at C-4 undergo regioselective homolytic substitutions at C-5 with nucleophilic 1,3,5-trioxanyl and ethoxycarbonyl radicals under Minisci conditions. Surprisingly, mainly 5,6-dihydro derivatives are formed in these reactions. Rearomatization with manganese dioxide leads to 4,5-disubstituted benzo[c][2,7]naphthyridines, which should be attractive building blocks for the synthesis of pyridoacridine alkaloids. Homolytic methylation at C-5 takes place with methyl radicals generated from acetic acid and acetaldehyde, respectively. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.04.023