4-(4-methoxyphenyl)-1H-pyrazole-3,5-diamine | 1393345-96-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(4-methoxyphenyl)-1H-pyrazole-3,5-diamine
• CAS: 1393345-96-4
• 化学式: C₁₀H₁₂N₄O
• 分子量: 204.231
• InChiKey: WFSSBPAIEOVYNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  90
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(4-methoxyphenyl)malononitrile 在 一水合肼 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 0.17h， 以92%的产率得到4-(4-methoxyphenyl)-1H-pyrazole-3,5-diamine
  参考文献：
  名称：

  A scalable approach to diaminopyrazoles using flow chemistry

  摘要：

  This Letter reports on how the combination of microwave and continuous flow chemistry facilitated the convenient preparation of aminopyrazoles from commercial aryl halides. The method was applied to a variety of substrates with good to excellent yields and further extended toward the complete flow synthesis of 5,7-dimethyl-3-phenylpyrazolo[1,5-a]pyrimidin-2-amine. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.05.152

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。
• A scalable approach to diaminopyrazoles using flow chemistry
  作者：Noel S. Wilson、Augustine T. Osuma、Jennifer A.Van Camp、Xiangdong Xu

  DOI：10.1016/j.tetlet.2012.05.152

  日期：2012.8

  This Letter reports on how the combination of microwave and continuous flow chemistry facilitated the convenient preparation of aminopyrazoles from commercial aryl halides. The method was applied to a variety of substrates with good to excellent yields and further extended toward the complete flow synthesis of 5,7-dimethyl-3-phenylpyrazolo[1,5-a]pyrimidin-2-amine. (c) 2012 Elsevier Ltd. All rights reserved.