3-hydroxy-4-trifluoromethyl-1H-pyrazolo[3,4-b]pyridin-5-carboxylic acid | 1270967-03-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并吡啶类
• 英文名称: 3-hydroxy-4-trifluoromethyl-1H-pyrazolo[3,4-b]pyridin-5-carboxylic acid
• 英文别名: 3-Oxo-4-(trifluoromethyl)-1,2-dihydropyrazolo[3,4-b]pyridine-5-carboxylic acid
• CAS: 1270967-03-7
• 化学式: C₈H₄F₃N₃O₃
• 分子量: 247.133
• InChiKey: VYPRAYAGBYVYHP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  91.3
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  乙氧基-2-亚甲基三氟乙酰乙酸乙酯 在 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 生成 3-hydroxy-4-trifluoromethyl-1H-pyrazolo[3,4-b]pyridin-5-carboxylic acid
  参考文献：
  名称：

  Peculiarities of cyclization of ethyl 2-ethoxymethylene-3-oxo-3-(polyfluoroalkyl)propionates with 3-amino-5-hydroxypyrazole

  摘要：

  The reactions of ethyl 2-ethoxymethylene-3-oxo-3-(polyfluoroalkyl)propionates with 3-amino-5-hydroxypyrazole result in ethyl 2,7-dihydroxy-7-(polyfluoroalkyl)-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-carboxylates under mild conditions. These products undergo recyclization in refluxing ethanol to form ethyl 3-hydroxy-4-(polyfluoroalkyl)-1H-pyrazolo[3,4-b]pyridin-5-carboxylates, whereas in refluxing glacial acetic acid they are dehydrated to ethyl 2-hydroxy-7-(polyfluoroalkyl)pyrazolo[1,5-a]pyrimidin-6-carboxylates. The non-fluorinated ethyl 2-ethoxymethylene-3-oxo esters in the reactions with 3-amino-5-hydroxypyrazole in ethanol (or glacial acetic acid) under reflux form only ethyl 2-hydroxy-7-phenyl(hydroxy)pyrazolo[1,5-c]pyrimidin-6-carboxylates. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2013.01.005

文献信息

• Peculiarities of cyclization of ethyl 2-ethoxymethylene-3-oxo-3-(polyfluoroalkyl)propionates with 3-amino-5-hydroxypyrazole
  作者：Marina V. Goryaeva、Yanina V. Burgart、Viktor I. Saloutin

  DOI：10.1016/j.jfluchem.2013.01.005

  日期：2013.3

  The reactions of ethyl 2-ethoxymethylene-3-oxo-3-(polyfluoroalkyl)propionates with 3-amino-5-hydroxypyrazole result in ethyl 2,7-dihydroxy-7-(polyfluoroalkyl)-4,7-dihydropyrazolo[1,5-a]pyrimidin-6-carboxylates under mild conditions. These products undergo recyclization in refluxing ethanol to form ethyl 3-hydroxy-4-(polyfluoroalkyl)-1H-pyrazolo[3,4-b]pyridin-5-carboxylates, whereas in refluxing glacial acetic acid they are dehydrated to ethyl 2-hydroxy-7-(polyfluoroalkyl)pyrazolo[1,5-a]pyrimidin-6-carboxylates. The non-fluorinated ethyl 2-ethoxymethylene-3-oxo esters in the reactions with 3-amino-5-hydroxypyrazole in ethanol (or glacial acetic acid) under reflux form only ethyl 2-hydroxy-7-phenyl(hydroxy)pyrazolo[1,5-c]pyrimidin-6-carboxylates. (C) 2013 Elsevier B.V. All rights reserved.