2-(6,7-dimethoxy-3-nitroquinolin-2-yl)phenol | 1363156-76-6

• 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: 2-(6,7-dimethoxy-3-nitroquinolin-2-yl)phenol
• CAS: 1363156-76-6
• 化学式: C₁₇H₁₄N₂O₅
• 分子量: 326.309
• InChiKey: VKKCJWCVOGTPPB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  94.72
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-(6,7-dimethoxy-3-nitroquinolin-2-yl)phenol 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 48.0h， 以93%的产率得到2-(3-amino-6,7-dimethoxyquinolin-2-yl)phenol
  参考文献：
  名称：

  Synthesis of heteroannulated 3-nitro- and 3-aminopyridines by cyclocondensation of electron-rich aminoheterocycles with 3-nitrochromone

  摘要：

  3-Nitrochromone reacts with electron-rich aminoheterocycles (in glacial acetic acid at reflux) and anilines (in a mixture of DMF and TMSCI at 100-140 degrees C) to give a variety of hetero(carbo)annulated 3-nitropyridines. The reaction, involving a formal [3+3] cyclocondensation, proceeds in high yields and appears not to be influences greatly by the nature of the 1,3-C,N-dinucleophile as seen from the thorough scope study. The synthetic utility of the products was demonstrated by their conversion into the corresponding 3-aminopyridine derivatives. An NMR study and X-ray crystallographic analysis are reported. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.101
• 作为产物：
  描述：

  2'-Hydroxy-ω-nitroacetophenone 在 三甲基氯硅烷 、 硫酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 生成 2-(6,7-dimethoxy-3-nitroquinolin-2-yl)phenol
  参考文献：
  名称：

  Synthesis of heteroannulated 3-nitro- and 3-aminopyridines by cyclocondensation of electron-rich aminoheterocycles with 3-nitrochromone

  摘要：

  3-Nitrochromone reacts with electron-rich aminoheterocycles (in glacial acetic acid at reflux) and anilines (in a mixture of DMF and TMSCI at 100-140 degrees C) to give a variety of hetero(carbo)annulated 3-nitropyridines. The reaction, involving a formal [3+3] cyclocondensation, proceeds in high yields and appears not to be influences greatly by the nature of the 1,3-C,N-dinucleophile as seen from the thorough scope study. The synthetic utility of the products was demonstrated by their conversion into the corresponding 3-aminopyridine derivatives. An NMR study and X-ray crystallographic analysis are reported. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.101

文献信息

• Synthesis of heteroannulated 3-nitro- and 3-aminopyridines by cyclocondensation of electron-rich aminoheterocycles with 3-nitrochromone
  作者：Viktor O. Iaroshenko、Satenik Mkrtchyan、Ashot Gevorgyan、Marcelo Vilches-Herrera、Dmitri V. Sevenard、Alexander Villinger、Tariel V. Ghochikyan、Ashot Saghiyan、Vyacheslav Ya. Sosnovskikh、Peter Langer

  DOI：10.1016/j.tet.2011.06.101

  日期：2012.3

  3-Nitrochromone reacts with electron-rich aminoheterocycles (in glacial acetic acid at reflux) and anilines (in a mixture of DMF and TMSCI at 100-140 degrees C) to give a variety of hetero(carbo)annulated 3-nitropyridines. The reaction, involving a formal [3+3] cyclocondensation, proceeds in high yields and appears not to be influences greatly by the nature of the 1,3-C,N-dinucleophile as seen from the thorough scope study. The synthetic utility of the products was demonstrated by their conversion into the corresponding 3-aminopyridine derivatives. An NMR study and X-ray crystallographic analysis are reported. (C) 2011 Elsevier Ltd. All rights reserved.