1-(6-Fluorobenzothiazol-2-yl)-4-phenyl-3-(p-tolyl)-6-trifluoromethyl-1H-pyrazolo[3,4-b]pyridine | 1384952-47-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(6-Fluorobenzothiazol-2-yl)-4-phenyl-3-(p-tolyl)-6-trifluoromethyl-1H-pyrazolo[3,4-b]pyridine
• 英文别名: 1-(6-Fluorobenzothiazol-2-yl)-4-phenyl-3-(p-tolyl)-6-fluoromethyl-1H-pyrazolo[3,4-b]pyridine
• CAS: 1384952-47-9
• 化学式: C₂₇H₁₆F₄N₄S
• 分子量: 504.51
• InChiKey: IFRDQONBNIMVEJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.83
• 重原子数：
  36.0
• 可旋转键数：
  3.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  43.6
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  苯甲酰三氟丙酮 、 6-氟-2(3h)-苯并噻唑酮肼酮 、 对甲苯酰乙腈 在 对甲苯磺酸 作用下， 反应 0.33h， 以84%的产率得到1-(6-Fluorobenzothiazol-2-yl)-4-phenyl-3-(p-tolyl)-6-trifluoromethyl-1H-pyrazolo[3,4-b]pyridine
  参考文献：
  名称：

  Multi-component solvent-free versus stepwise solvent mediated reactions: Regiospecific formation of 6-trifluoromethyl and 4-trifluoromethyl-1H-pyrazolo[3,4-b]pyridines

  摘要：

  A simple and efficient regiospecific synthesis of 6-trifluoromethyl-1H-pyrazolo[3,4-b]pyridines has been achieved in excellent yields via a three-component reaction between 2-hydrazinobenzothiazoles, alpha-cyanoacetophenones and trifiuoromethyl-beta-diketones under solvent-free conditions. This method was found to be more convenient than the classical stepwise solvent mediated process, which furnished not only the opposite regioisomer i.e. 4-trifluoromethyl-1H-pyrazolo[3,4-b]pyridines (50-60%) but also an undesired amide, 5-acetylamino-1-(benzothiazol-2'-yl)-3-phenyl-1H-pyrazole as a side product. The structure of the two regioisomers was established with certainty on the basis of rigorous analysis of H-1, C-13, F-19-NMR spectral data and (H-1-C-13) gs-HMQC, (H-1-C-13) gs-HMBC experiments. (C) 2012 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jfluchem.2012.04.007