1-(3,5-dinitro-1H-pyrazole-4-yl)azepane | 1256258-12-4

• 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: 1-(3,5-dinitro-1H-pyrazole-4-yl)azepane
• 英文别名: 1-(3,5-dinitro-1H-pyrazol-4-yl)azepane
• CAS: 1256258-12-4
• 化学式: C₉H₁₃N₅O₄
• 分子量: 255.233
• InChiKey: ZOYQIOIISLQAQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  124
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  环己亚胺 、 4-chloro-3,5-dinitropyrazole 在 硫酸 作用下， 以 水 为溶剂， 反应 18.0h， 以83%的产率得到1-(3,5-dinitro-1H-pyrazole-4-yl)azepane
  参考文献：
  名称：

  Efficient Procedure for High-Yield Synthesis of 4-Substituted 3,5-Dinitropyrazoles Using 4-Chloro-3,5-dinitropyrazole

  摘要：

  The transformations of readily available 4-chloro-3,5-dinitropyrazole and its N-methylated derivative under the action of anionic S-/O-nucleophiles and neutral N-nucleophiles were studied. Independent of the substrate's charge (anionic, R = H, or neutral, R = Me), the nucleophilic substitution proceeds exclusively at position 4 replacing the chlorine nucleofuge. As a result of this study, the effective synthetic method for the preparation of 4-substituted 3,5-dinitropyrazoles via the nucleophilic substitution in 4-chloro3,5-dinitropyrazole was elaborated.

  DOI：

  10.1055/s-0031-1291134

文献信息

• Synthesis and Comparison of the Reactivity of 3,4,5-1<i>H</i>-Trinitropyrazole and Its<i>N</i>-Methyl Derivative
  作者：Igor L. Dalinger、Irina A. Vatsadze、Tatyana K. Shkineva、Galina P. Popova、Svyatoslav A. Shevelev、Yuliya V. Nelyubina

  DOI：10.1002/jhet.1026

  日期：2013.7

  (1) has been obtained via nitration of 3,5‐dinitropyrazole with mixture of sulfuric and nitric acids. Compound 1 reacts with excess ammonia and aliphatic amines, in the presence of bases with NH‐azoles, phenols, thiols, and triflouroethanol at mild conditions in water. All these reactions occur as the nucleophilic substitution of the nitro‐group at position 4 in 1 affording 4‐R‐3,5‐dinitropyrazoles.

  3,4,5-三硝基-1 H-吡唑（1）是通过将3,5-二硝基吡唑与硫酸和硝酸的混合物硝化而获得的。在碱的存在下，化合物1在水中在温和条件下与过量的氨和脂肪胺反应，并与NH-唑，酚，硫醇和三氟乙醇反应。所有这些反应均发生在位置1的4位上的硝基被亲核取代后，得到4-R-3,5-二硝基吡唑。甲基化的产物1，Ñ甲基-3,4,5- trinitropyrazole（4）也与硫醇，酚，肟，氨，胺和NH-唑类反应。反应以高收率进行，但在这些情况下，亲核取代发生在区域4中的5位区域选择性，产生5-R-3,4-二硝基吡唑。
• The specific reactivity of 3,4,5-trinitro-1H-pyrazole
  作者：Igor L. Dalinger、Irina A. Vatsadze、Tatyana K. Shkineva、Galina P. Popova、Svyatoslav A. Shevelev

  DOI：10.1016/j.mencom.2010.09.003

  日期：2010.9

  Nitration of 3,5-dinitropyrazole with HNO3-H2SO4 mixture gives 3,4,5-trinitro-1H-pyrazole, which in reaction with ammonia, amines or thiols under mild conditions undergoes regioselective nucleophilic substitution of the 4-positioned nitro group