5-acetylamino-1-(6-fluorobenzothiazol-2-yl)-3-(p-tolyl)-1H-pyrazole | 1384952-56-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-acetylamino-1-(6-fluorobenzothiazol-2-yl)-3-(p-tolyl)-1H-pyrazole
• CAS: 1384952-56-0
• 化学式: C₁₉H₁₅FN₄OS
• 分子量: 366.419
• InChiKey: CUCMACLDDVYYDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.55
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  59.81
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  三氟乙酰丙酮 、 5-amino-1-(6-fluorobenzothiazol-2-yl)-3-(p-tolyl)-1-H-pyrazole 、 溶剂黄146 反应 10.0h， 生成 5-acetylamino-1-(6-fluorobenzothiazol-2-yl)-3-(p-tolyl)-1H-pyrazole 、 1-(6-fluorobenzothiazol-2-yl)-6-methyl-3-(p-tolyl)-4-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