3-nitro-5-guanidino-1,2,4-oxadiazole | 1352659-05-2

• 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-nitro-5-guanidino-1,2,4-oxadiazole
• 英文别名: 3-Nitro-5-guanidino-1,2,4-oxadiazole；2-(3-nitro-1,2,4-oxadiazol-5-yl)guanidine
• CAS: 1352659-05-2
• 化学式: C₃H₄N₆O₃
• 分子量: 172.103
• InChiKey: RAYJPXFQDDWCRU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  149
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-nitro-5-guanidino-1,2,4-oxadiazole 在 硫酸 、 硝酸 、 碳酸氢钠 作用下， 以 水 为溶剂， 反应 192.0h， 以7.7%的产率得到3-nitro-5-amino-1,2,4-oxadiazole
  参考文献：
  名称：

  Synthesis and Characterization of Energetic 3-Nitro-1,2,4-oxadiazoles

  摘要：

  All new: 3-Nitro-5-guanidino-1,2,4-oxadiazole (NOG) was synthesized from diaminoglycoluril with in situ generated dimethyldioxirane (DMDO). The impact sensitivity of NOG is more than 40 J with a decomposition temperature of 290 °C. Some other energetic derivatives have been prepared and characterized.

  DOI：

  10.1002/chem.201103159
• 作为产物：
  描述：

  glycoluril 3a,6a-diamine 在 Oxone 、 碳酸氢钠 、 丙酮 作用下， 以 水 、 乙腈 为溶剂， 反应 10.5h， 以40%的产率得到3-nitro-5-guanidino-1,2,4-oxadiazole
  参考文献：
  名称：

  Synthesis and Characterization of Energetic 3-Nitro-1,2,4-oxadiazoles

  摘要：

  All new: 3-Nitro-5-guanidino-1,2,4-oxadiazole (NOG) was synthesized from diaminoglycoluril with in situ generated dimethyldioxirane (DMDO). The impact sensitivity of NOG is more than 40 J with a decomposition temperature of 290 °C. Some other energetic derivatives have been prepared and characterized.

  DOI：

  10.1002/chem.201103159

文献信息

• Polymer-Supported Enantioselective Bifunctional Catalysts for Nitro-Michael Addition of Ketones and Aldehydes
  作者：Lital Tuchman-Shukron、Scott J. Miller、Moshe Portnoy

  DOI：10.1002/chem.201102474

  日期：2012.2.20

  L‐amino acid as a spacer and a urea‐forming moiety in a polymer‐supported bifunctional urea–primary amine catalyst, based on (1R, 2R)‐(+)‐1,2‐diphenylethylenediamine, significantly improves the catalyst’s activity and stereoselectivity in the asymmetric addition of ketones and aldehydes to nitroolefins. Yields and enantioselectivities, unprecedented for immobilized catalysts, were obtained with such challenging

  在基于（1 R，2 R）-（+）-1,2-二苯基乙二胺的聚合物负载型双官能尿素-伯胺催化剂中引入L-氨基酸作为间隔基和形成尿素的部分可显着改善酮和醛不对称加成到硝基烯烃中时催化剂的活性和立体选择性。用丙酮，环戊酮和α，α-二取代醛等具有挑战性的给体获得了固定化催化剂前所未有的收率和对映选择性，这通常在该反应中表现不佳（特别是在使用基于仲胺的催化剂时）。值得注意的是，尽管在所研究的催化剂中，D-氨基酸作为间隔基显着低于L 异构体，对于所选的二胺构型（匹配-不匹配对），氨基酸侧链的大小几乎不会影响催化剂的对映选择性。这些结果，与所述催化剂与带有两个吸电子基团和催化剂类似物的基于叔胺（而不是伯）胺的行为基板的反应性分布曲线相结合，表明烯胺-涉及加成机制和特定的有序Ç  C键形成的过渡态负责高对映选择性的催化反应。
• Synthesis and characteristics of a novel, high-nitrogen, heat-resistant, insensitive material (NOG₂Tz)
  作者：Zhanda Fu、Cheng He、Fu-xue Chen

  DOI：10.1039/c1jm14232a

  日期：——

  The novel, high-nitrogen, energetic compound, 3,6-bis(3-nitro-1,2,4-oxadiazole-5-guanyl)-1,2,4,5-tetrazine (NOG2Tz, 8, N 53.08%), was synthesised and fully characterised. Thermal decomposition kinetics and several thermodynamic parameters were obtained under non-isothermal conditions by DSC. NOG2Tz exhibits a high density and was calculated to have favourable detonation properties. It is thermally stable (Tdec. 328 °C) and remarkably insensitive to impact.

  合成了新型高氮高能化合物 3,6-双（3-硝基-1,2,4-恶二唑-5-鸟嘌呤基）-1,2,4,5-四嗪（NOG2Tz，8，N 53.08%），并对其进行了全面表征。在非等温条件下，通过 DSC 获得了热分解动力学和几个热力学参数。NOG2Tz 密度较高，经计算具有良好的引爆特性。它具有热稳定性（Tdec. 328 °C），对冲击明显不敏感。
• Synthesis and Characterization of Energetic 3-Nitro-1,2,4-oxadiazoles
  作者：Zhanda Fu、Rui Su、Yang Wang、Yao-Feng Wang、Wei Zeng、Nan Xiao、Yukai Wu、Zhiming Zhou、Jun Chen、Fu-Xue Chen

  DOI：10.1002/chem.201103159

  日期：2012.2.13

  All new: 3-Nitro-5-guanidino-1,2,4-oxadiazole (NOG) was synthesized from diaminoglycoluril with in situ generated dimethyldioxirane (DMDO). The impact sensitivity of NOG is more than 40 J with a decomposition temperature of 290 °C. Some other energetic derivatives have been prepared and characterized.