ethyl 3-amino-1-(4-methoxyphenyl)-1H-pyrazole-4-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 3-amino-1-(4-methoxyphenyl)-1H-pyrazole-4-carboxylate
• 英文别名: ethyl 3-amino-1-(4-methoxyphenyl)pyrazole-4-carboxylate
• 化学式: C₁₃H₁₅N₃O₃
• 分子量: 261.28
• InChiKey: SZXBVVZRENGLOU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  79.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3-amino-1-(4-methoxyphenyl)-1H-pyrazole-4-carboxylate 在 亚硝酸异戊酯 作用下， 以 四氢呋喃 为溶剂， 生成 ethyl 1-(4-methoxyphenyl)-1H-pyrazole-4-carboxylate
  参考文献：
  名称：

  Synthesis and structure–activity relationships of 1-Phenylpyrazoles as xanthine oxidase inhibitors

  摘要：

  A series of 1-phenylpyrazoles was evaluated for inhibitory activity against xanthine oxidase in vitro. Of the compounds prepared, 1-(3-cyano-4-neopentyloxyphenyl)pyrazole-4-carboxylic acid (Y-700) had the most potent enzyme inhibition and displayed longer-lasting hypouricemic action than did allopurinol in a rat model of hyperuricemia induced by the uricase inhibitor potassium oxonate. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00093-2
• 作为产物：
  描述：

  (4-甲氧基苯基)肼 、 2-氰基-3-乙氧基丙烯酸乙酯 以 乙醇 为溶剂， 生成 ethyl 3-amino-1-(4-methoxyphenyl)-1H-pyrazole-4-carboxylate
  参考文献：
  名称：

  Synthesis and structure–activity relationships of 1-Phenylpyrazoles as xanthine oxidase inhibitors

  摘要：

  A series of 1-phenylpyrazoles was evaluated for inhibitory activity against xanthine oxidase in vitro. Of the compounds prepared, 1-(3-cyano-4-neopentyloxyphenyl)pyrazole-4-carboxylic acid (Y-700) had the most potent enzyme inhibition and displayed longer-lasting hypouricemic action than did allopurinol in a rat model of hyperuricemia induced by the uricase inhibitor potassium oxonate. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00093-2

文献信息

• A Michael Equilibration Model To Control Site Selectivity in the Condensation toward Aminopyrazoles
  作者：Daniel R. Fandrick、Sanjit Sanyal、Joseph Kaloko、Jason A. Mulder、Yuwen Wang、Ling Wu、Heewon Lee、Frank Roschangar、Matthias Hoffmann、Chris H. Senanayake

  DOI：10.1021/acs.orglett.5b01248

  日期：2015.6.19

  A Michael equilibration model is presented to provide for site-selective pyrazole condensations between alkoxyacrylonitriles and hydrazines. Both pyrazole isomers were accessed with high selectivity by employment of kinetically or thermodynamically controlled conditions. Substrate scope and identification of Michael intermediates, as well as competitive pathways, support the presented mechanistic proposal

  提出了迈克尔平衡模型，以提供烷氧基丙烯腈和肼之间的位点选择性吡唑缩合。通过采用动力学或热力学控制条件，可以高选择性地获得两种吡唑异构体。迈克尔中间体的底物范围和鉴定，以及竞争途径，为提出的机械方案提供了支持。桑德迈尔的衍生化作用提供了对完全取代的吡唑的位置选择的途径。