3,5-dinitro-4-phenoxy-1H-pyrazole | 1399565-39-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,5-dinitro-4-phenoxy-1H-pyrazole
• CAS: 1399565-39-9
• 化学式: C₉H₆N₄O₅
• 分子量: 250.17
• InChiKey: IAYGUBMEEDIWNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  130
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-chloro-3,5-dinitropyrazole 、 苯酚 在 sodium hydroxide 、 硫酸 作用下， 以 水 为溶剂， 反应 12.17h， 以90%的产率得到3,5-dinitro-4-phenoxy-1H-pyrazole
  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 of 4-substituted pyrazole-3,5-diamines <i>via</i> Suzuki–Miyaura coupling and iron-catalyzed reduction
  作者：Monika Tomanová、Lukáš Jedinák、Jan Košař、Lubomír Kvapil、Pavel Hradil、Petr Cankař

  DOI：10.1039/c7ob02373a

  日期：——

  A general and efficient synthesis of 4-substituted-1H-pyrazole-3,5-diamines was developed to access derivatives with an aryl, heteroaryl, or styryl group, which are otherwise relatively difficult to prepare. The first step is based on the Suzuki–Miyaura cross-coupling reaction utilizing the XPhos Pd G2 precatalyst. The coupling reactions of 4-bromo-3,5-dinitro-1H-pyrazole with the electron-rich/deficient

  为了获得具有芳基，杂芳基或苯乙烯基的衍生物，开发了一般且有效的4-取代的-1 H-吡唑-3，5-二胺的合成，否则这些衍生物很难制备。第一步是基于XPhos Pd G2预催化剂的Suzuki-Miyaura交叉偶联反应。4-溴-3,5-二硝基-1 H-吡唑与富电子/缺乏电子或对空间要求高的硼酸的偶合反应使得能够生产相应的二硝基吡唑。随后用水合肼的铁催化的两个硝基还原都完成了合成。4-甲氧基苯乙烯基衍生物的另外的脱甲基作用允许产生作为选择性CDK9抑制剂报道的CAN508的碳模拟物。
• 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。