4-aminopyrazole-3,5-dicarboxylic acid

• 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-aminopyrazole-3,5-dicarboxylic acid
• 英文别名: 4-amino-1H-pyrazole-3,5-dicarboxylic acid
• 化学式: C₅H₅N₃O₄
• 分子量: 171.112
• InChiKey: IGUCGPRNZVGVNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  129
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3,5-二甲基-4-硝基吡唑 在 potassium permanganate 、 sodium dithionite 作用下， 生成 4-aminopyrazole-3,5-dicarboxylic acid
  参考文献：
  名称：

  Four Syntheses of 4-Amino-3,5-dinitropyrazole

  摘要：

  In this paper, syntheses of 4‐amino‐3,5‐dinitropyrazole from four different starting materials are described. The starting materials were 4‐nitropyrazole, 4‐nitro‐3,5‐dimethylpyrazole, 3,5‐dinitropyrazole, and 4‐chloropyrazole, respectively. They are compared in terms of yield, number of steps and suitability for scale‐up into pilot scale production. The overall yield, calculated from commercially available starting materials, ranged from 21% in the case of synthesis via 3,5‐dinitropyrazole up to 61% for the one starting from 4‐chloropyrazole. With numerous factors taken into account, the latter was chosen for a pilot scale study and the product could be produced in batches of 200 g.

  DOI：

  10.1002/jhet.1725

文献信息

• Identification of the <i>C</i> ‐Glycoside Synthases during Biosynthesis of the Pyrazole‐ <i>C</i> ‐Nucleosides Formycin and Pyrazofurin
  作者：Daan Ren、Shao‐An Wang、Yeonjin Ko、Yujie Geng、Yasushi Ogasawara、Hung‐wen Liu

  DOI：10.1002/anie.201910356

  日期：2019.11.11

  linkage between the heterocyclic base and the ribofuranose ring. While the biosynthesis of pseudouridine-C-nucleosides has been studied, less is known about the pyrazole-C-nucleosides such as the formycins and pyrazofurin. Herein, genome screening of Streptomyces candidus NRRL 3601 led to the discovery of the pyrazofurin biosynthetic gene cluster pyf. In vitro characterization of gene product PyfQ demonstrated

  C-核苷的特征在于杂环碱基与呋喃核糖环之间的CC键而不是CN键。虽然已经研究了伪尿苷-C-核苷的生物合成，但是对于吡唑-C-核苷如甲霉素和吡唑呋林的了解较少。在此，对链霉菌NRRL 3601的基因组筛选导致发现了吡唑并呋喃生物合成基因簇pyf。基因产物PyfQ的体外表征表明，它能够催化由4-羟基-1H-吡唑-3,5-二羧酸和磷酸核糖焦磷酸（PRPP）形成C-糖苷羧基羟基吡唑核糖核苷酸（CHPR）。类似地，ForT，一种在霉菌素途径中的PyfQ同源物，可以催化4-氨基-1H-吡唑-3,5-二羧酸和PRPP的偶联，形成羧氨基吡唑核糖核苷酸。最后，
• Four Syntheses of 4-Amino-3,5-dinitropyrazole
  作者：Stefan Ek、Nikolaj V. Latypov

  DOI：10.1002/jhet.1725

  日期：2014.11

  In this paper, syntheses of 4‐amino‐3,5‐dinitropyrazole from four different starting materials are described. The starting materials were 4‐nitropyrazole, 4‐nitro‐3,5‐dimethylpyrazole, 3,5‐dinitropyrazole, and 4‐chloropyrazole, respectively. They are compared in terms of yield, number of steps and suitability for scale‐up into pilot scale production. The overall yield, calculated from commercially available starting materials, ranged from 21% in the case of synthesis via 3,5‐dinitropyrazole up to 61% for the one starting from 4‐chloropyrazole. With numerous factors taken into account, the latter was chosen for a pilot scale study and the product could be produced in batches of 200 g.