6-(2-hydroxyphenyl)-5-nitro-2-phenyl-1,2-dihydropyrazolo[3,4-b]pyridin-3-one | 1363156-68-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 6-(2-hydroxyphenyl)-5-nitro-2-phenyl-1,2-dihydropyrazolo[3,4-b]pyridin-3-one
• 英文别名: 6-(2-hydroxyphenyl)-5-nitro-2-phenyl-1H-pyrazolo[3,4-b]pyridin-3-one
• CAS: 1363156-68-6
• 化学式: C₁₈H₁₂N₄O₄
• 分子量: 348.318
• InChiKey: AZHJBEGVDBNSDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-(2-hydroxyphenyl)-5-nitro-2-phenyl-1,2-dihydropyrazolo[3,4-b]pyridin-3-one 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78%的产率得到5-amino-6-(2-hydroxyphenyl)-2-phenyl-1,2-dihydropyrazolo[3,4-b]pyridin-3-one
  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：

  4-羟基香豆素 在 硫酸 、 水 、 硝酸 、 溶剂黄146 、 sodium hydroxide 、 sodium nitrite 作用下， 反应 14.25h， 生成 6-(2-hydroxyphenyl)-5-nitro-2-phenyl-1,2-dihydropyrazolo[3,4-b]pyridin-3-one
  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