3-(4-chlorophenyl)-1-(4-nitrophenyl)-1H-pyrazolo[3,4-b]pyrazine | 1018831-51-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4-chlorophenyl)-1-(4-nitrophenyl)-1H-pyrazolo[3,4-b]pyrazine
• 英文别名: 3-(4-Chlorophenyl)-1-(4-nitrophenyl)pyrazolo[3,4-b]pyrazine
• CAS: 1018831-51-0
• 化学式: C₁₇H₁₀ClN₅O₂
• 分子量: 351.752
• InChiKey: DNHOBHSQYATTQH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  25
• 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：
  89.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-硝基苯肼盐酸盐 、 (4-chlorophenyl)(pyrazin-2-yl)methanone 在 盐酸 作用下， 以 乙醇 为溶剂， 以55%的产率得到3-(4-chlorophenyl)-1-(4-nitrophenyl)-1H-pyrazolo[3,4-b]pyrazine
  参考文献：
  名称：

  A New Cyclization to Fused Pyrazoles Tunable for Pericyclic or Pseudopericyclic Route: An Experimental and Theoretical Study

  摘要：

  2-Pyrazinyl (2) and 3-pyridazinylketone arylhydrazones (6) and their benzologues undergo a ring closure reaction to yield pyrazolo[3,4-b]pyrazines (4) and pyrazolo[4,3-c]pyridazines (7), respectively, in acceptable to good yields. The reaction was found to be accelerated by using acidic or basic conditions. Quantum chemical calculations suggest the key step of the mechanism to be a direct cyclization; analysis of aromaticity based on computed magnetic properties revealed its medium-dependent pericyclic or pseudopericyclic character. The cyclization reaction has also been extended for the synthesis of related ring systems (9, 12, 14).

  DOI：

  10.1021/jo800483a

文献信息

• A New Cyclization to Fused Pyrazoles Tunable for Pericyclic or Pseudopericyclic Route: An Experimental and Theoretical Study
  作者：László Filák、Tibor András Rokob、Gyöngyvér Ágnes Vaskó、Orsolya Egyed、Ágnes Gömöry、Zsuzsanna Riedl、György Hajós

  DOI：10.1021/jo800483a

  日期：2008.5.1

  2-Pyrazinyl (2) and 3-pyridazinylketone arylhydrazones (6) and their benzologues undergo a ring closure reaction to yield pyrazolo[3,4-b]pyrazines (4) and pyrazolo[4,3-c]pyridazines (7), respectively, in acceptable to good yields. The reaction was found to be accelerated by using acidic or basic conditions. Quantum chemical calculations suggest the key step of the mechanism to be a direct cyclization; analysis of aromaticity based on computed magnetic properties revealed its medium-dependent pericyclic or pseudopericyclic character. The cyclization reaction has also been extended for the synthesis of related ring systems (9, 12, 14).