3-Nitropyridin-4D1 | 22526-99-4

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 3-Nitropyridin-4D1
• CAS: 22526-99-4
• 化学式: C₅H₄N₂O₂
• 分子量: 125.091
• InChiKey: QLILRKBRWXALIE-VMNATFBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.99
• 重原子数：
  9.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  56.03
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  3-硝基吡啶 在 重水 、 caesium carbonate 、 silver carbonate 作用下， 以 touene 为溶剂， 反应 22.0h， 以8%的产率得到2-D-3-nitropyridine
  参考文献：
  名称：

  C–H Arylation of Pyridines: High Regioselectivity as a Consequence of the Electronic Character of C–H Bonds and Heteroarene Ring

  摘要：

  We report a new catalytic protocol for highly selective C-H arylation of pyridines containing common and synthetically versatile electron-withdrawing substituents (NO(2), CN, F and Cl). The new protocol expands the scope of catalytic azine functionalization as the excellent regioselectivity at the 3- and 4-positions well complements the existing methods for C-H arylation and Ir-catalyzed borylation, as well as classical functionalization of pyridines. Another important feature of the new method is its flexibility to adapt to challenging substrates by a simple modification of the carboxylic acid ligand or the use of silver salts. The regioselectivity can be rationalized on the basis of the key electronic effects (repulsion between the nitrogen lone pair and polarized C-Pd bond at C2-/C6-positions and acidity of the C-H bond) in combination with steric effects (sensitivity to bulky substituents).

  DOI：

  10.1021/ja206022p