1H,4H-3-methoxycarbonyl-6-nitropyrazolo<4,3-c>pyrazole | 161155-33-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并吡唑类
• 英文名称: 1H,4H-3-methoxycarbonyl-6-nitropyrazolo<4,3-c>pyrazole
• 英文别名: 1H,4H-3-methoxycarbonyl-6-nitropyrazolo[4,3-c]pyrazole；Methyl 6-nitro-1,4-dihydropyrazolo[4,3-c]pyrazole-3-carboxylate；methyl 3-nitro-2,4-dihydropyrazolo[4,3-c]pyrazole-6-carboxylate
• CAS: 161155-33-5
• 化学式: C₆H₅N₅O₄
• 分子量: 211.137
• InChiKey: UCVJGULVAOCFTF-UHFFFAOYSA-N

物化性质

• 沸点：
  523.0±45.0 °C(Predicted)
• 密度：
  1.814±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1H,4H-3-methoxycarbonyl-6-nitropyrazolo<4,3-c>pyrazole 在 ammonium hydroxide 作用下， 以80.6 %的产率得到1H,4H-3-carbamoyl-6-nitropyrazolo<4,3-c>pyrazole
  参考文献：
  名称：

  基于新型霍夫曼型重排的高能 7-Nitro-3,5-dihydro-4H-pyrazolo[4,3-d][1,2,3]triazin-4-one 的合成

  摘要：

  重排反应是有机合成中的有效策略，对含能材料的发展做出了巨大贡献。在这里，我们报告了基于 7-nitro-3,5-dihydro-4H-pyrazolo[4,3-d][1,2,3]triazin-4-one (NPTO) 的稠合能量结构的制备一种新颖的霍夫曼型重排。1,2,3-三嗪单元首次从吡唑单元引入稠合双环骨架。使用多核 NMR 和 IR 光谱、元素分析以及 X 射线衍射研究对 NPTO 的新化合物进行了全面表征。通过差示扫描量热法 (DSC-TG) 方法和EXPLO5研究了 NPTO 的热行为和爆轰特性分别基于程序的计算。计算结果表明，NPTO与含能材料DNPP和ANPP的爆轰性能相似，表明NPTO在钝感炸药和推进剂中具有良好的应用前景。

  DOI：

  10.3390/molecules26237319
• 作为产物：
  描述：

  1H,4H-3-methyl-6-nitropyrazolo<4,3-c>pyrazole 在 氯化亚砜 、 sodium dichromate 、 硫酸 作用下， 反应 5.5h， 生成 1H,4H-3-methoxycarbonyl-6-nitropyrazolo<4,3-c>pyrazole
  参考文献：
  名称：

  Nitropyrazoles

  摘要：

  A method of synthesizing nitro derivatives of 1H,4H-pyrazolo[4,3-c]pyrazole is developed, and some of its transformations are studied. 3-Methyl-6-nitro-, 3-carboxy(methoxy-carbonyl, carbamoyl)-6-nitro-, 3-amino-6-nitro-, 3-nitro-, 3,6-dinitro-, 1,4-diacetonyl-3,6-dinitro-, and 1H,4H-3-aminopyrazolo[4,3-c]pyrazoles were obtained from 1H,4H-3-methylpyrazolo[4,3-c]pyrazole. Unsubstituted 1H,4H-pyrazolo[4,3-c]pyrazole, the first member of this series, was obtained for the first time. The compounds prepared were characterized by H-1, C-13, N-14, and N-15 NMR spectroscopy. NH-Acidity and basicity of the series of pyrazolo[4,3-c]pyrazoles synthesized is studied and the effect of the fused pyrazole ring on these properties is examined.

  DOI：

  10.1007/bf00704200

文献信息

• Nitropyrazoles
  作者：S. A. Shevelev、I. L. Dalinger、T. K. Shkineva、B. I. Ugrak、V. I. Gulevskaya、M. I. Kanishchev

  DOI：10.1007/bf00704200

  日期：1993.6

  A method of synthesizing nitro derivatives of 1H,4H-pyrazolo[4,3-c]pyrazole is developed, and some of its transformations are studied. 3-Methyl-6-nitro-, 3-carboxy(methoxy-carbonyl, carbamoyl)-6-nitro-, 3-amino-6-nitro-, 3-nitro-, 3,6-dinitro-, 1,4-diacetonyl-3,6-dinitro-, and 1H,4H-3-aminopyrazolo[4,3-c]pyrazoles were obtained from 1H,4H-3-methylpyrazolo[4,3-c]pyrazole. Unsubstituted 1H,4H-pyrazolo[4,3-c]pyrazole, the first member of this series, was obtained for the first time. The compounds prepared were characterized by H-1, C-13, N-14, and N-15 NMR spectroscopy. NH-Acidity and basicity of the series of pyrazolo[4,3-c]pyrazoles synthesized is studied and the effect of the fused pyrazole ring on these properties is examined.
• Synthesis of Energetic 7-Nitro-3,5-dihydro-4H-pyrazolo[4,3-d][1,2,3]triazin-4-one Based on a Novel Hofmann-Type Rearrangement
  作者：Fu-Qiang Bi、Yi-Fen Luo、Jun-Lin Zhang、Huan Huo、Bo-Zhou Wang

  DOI：10.3390/molecules26237319

  日期：——

  studies. The thermal behaviors and detonation properties of NPTO were investigated through a differential scanning calorimetry (DSC-TG) approach and EXPLO5 program-based calculations, respectively. The calculation results showed similar detonation performances between NPTO and the energetic materials of DNPP and ANPP, indicating that NPTO has a good application perspective in insensitive explosives and

  重排反应是有机合成中的有效策略，对含能材料的发展做出了巨大贡献。在这里，我们报告了基于 7-nitro-3,5-dihydro-4H-pyrazolo[4,3-d][1,2,3]triazin-4-one (NPTO) 的稠合能量结构的制备一种新颖的霍夫曼型重排。1,2,3-三嗪单元首次从吡唑单元引入稠合双环骨架。使用多核 NMR 和 IR 光谱、元素分析以及 X 射线衍射研究对 NPTO 的新化合物进行了全面表征。通过差示扫描量热法 (DSC-TG) 方法和EXPLO5研究了 NPTO 的热行为和爆轰特性分别基于程序的计算。计算结果表明，NPTO与含能材料DNPP和ANPP的爆轰性能相似，表明NPTO在钝感炸药和推进剂中具有良好的应用前景。