1-[6-(3,5-Dimethyl-1H-pyrazole-1-yl)-2-pyridyl]-3,5-bis(trifluoromethyl)-4,5-dihydro-1H-pyrazole-5-ol | 1560666-96-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 1-[6-(3,5-Dimethyl-1H-pyrazole-1-yl)-2-pyridyl]-3,5-bis(trifluoromethyl)-4,5-dihydro-1H-pyrazole-5-ol
• 英文别名: 2-[6-(3,5-dimethylpyrazol-1-yl)pyridin-2-yl]-3,5-bis(trifluoromethyl)-4H-pyrazol-3-ol
• CAS: 1560666-96-7
• 化学式: C₁₅H₁₃F₆N₅O
• 分子量: 393.292
• InChiKey: OXOIZWAHQAHOOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  66.5
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1-[6-(3,5-Dimethyl-1H-pyrazole-1-yl)-2-pyridyl]-3,5-bis(trifluoromethyl)-4,5-dihydro-1H-pyrazole-5-ol 在 硫酸 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 10.0h， 生成 C₁₅H₁₁Cl₃F₆N₅Ru
  参考文献：
  名称：

  Ruthenium Complex Catalysts Supported by a Bis(trifluoromethyl)pyrazolyl–Pyridyl-Based NNN Ligand for Transfer Hydrogenation of Ketones

  摘要：

  Ru(III) and Ru(II) complexes bearing a tridentate 2-(3',5'-dimethylpyrazol-1'-yl)-6-(3",5"-bis(trifluoromethyl)pyrazol-1"-yl)pyridine or 2-(benzimidazol-2'-yl)-6-(3",5"-bis(trifluoromethyl)pyrazol-1"-yl)-pyridine ligand were synthesized and applied to the transfer hydrogenation of ketones. The Ru(II) complex was structurally confirmed by the X-ray crystallographic analysis and achieved up to 2150 turnover numbers and final TOFs up to 29700 h(-1) in the transfer hydrogenation of ketones. The benzimidazolyl moiety with an unprotected NH functionality in the ligand exhibited an enhancement effect on the catalytic activity of its RuCl3 complex in the ketone reduction reactions, reaching a final TOF value up to 35640 h(-1). The controlled experiments have revealed that the compatibility of the trifluoromethylated pyrazolyl and unprotected benzimidazolyl is crucial for the establishment of the highly active catalytic system.

  DOI：

  10.1021/om401144u
• 作为产物：
  描述：

  2-bromo-6-(3,5-dimethyl-1H-pyrazol-1-yl)pyridine 在 hydrazine hydrate 、 三氟乙酸 作用下， 以 四氢呋喃 、 正丁醇 为溶剂， 反应 32.0h， 生成 1-[6-(3,5-Dimethyl-1H-pyrazole-1-yl)-2-pyridyl]-3,5-bis(trifluoromethyl)-4,5-dihydro-1H-pyrazole-5-ol
  参考文献：
  名称：

  Ruthenium Complex Catalysts Supported by a Bis(trifluoromethyl)pyrazolyl–Pyridyl-Based NNN Ligand for Transfer Hydrogenation of Ketones

  摘要：

  Ru(III) and Ru(II) complexes bearing a tridentate 2-(3',5'-dimethylpyrazol-1'-yl)-6-(3",5"-bis(trifluoromethyl)pyrazol-1"-yl)pyridine or 2-(benzimidazol-2'-yl)-6-(3",5"-bis(trifluoromethyl)pyrazol-1"-yl)-pyridine ligand were synthesized and applied to the transfer hydrogenation of ketones. The Ru(II) complex was structurally confirmed by the X-ray crystallographic analysis and achieved up to 2150 turnover numbers and final TOFs up to 29700 h(-1) in the transfer hydrogenation of ketones. The benzimidazolyl moiety with an unprotected NH functionality in the ligand exhibited an enhancement effect on the catalytic activity of its RuCl3 complex in the ketone reduction reactions, reaching a final TOF value up to 35640 h(-1). The controlled experiments have revealed that the compatibility of the trifluoromethylated pyrazolyl and unprotected benzimidazolyl is crucial for the establishment of the highly active catalytic system.

  DOI：

  10.1021/om401144u

文献信息

• Ruthenium Complex Catalysts Supported by a Bis(trifluoromethyl)pyrazolyl–Pyridyl-Based NNN Ligand for Transfer Hydrogenation of Ketones
  作者：Wangming Du、Qingfu Wang、Liandi Wang、Zhengkun Yu

  DOI：10.1021/om401144u

  日期：2014.2.24

  Ru(III) and Ru(II) complexes bearing a tridentate 2-(3',5'-dimethylpyrazol-1'-yl)-6-(3",5"-bis(trifluoromethyl)pyrazol-1"-yl)pyridine or 2-(benzimidazol-2'-yl)-6-(3",5"-bis(trifluoromethyl)pyrazol-1"-yl)-pyridine ligand were synthesized and applied to the transfer hydrogenation of ketones. The Ru(II) complex was structurally confirmed by the X-ray crystallographic analysis and achieved up to 2150 turnover numbers and final TOFs up to 29700 h(-1) in the transfer hydrogenation of ketones. The benzimidazolyl moiety with an unprotected NH functionality in the ligand exhibited an enhancement effect on the catalytic activity of its RuCl3 complex in the ketone reduction reactions, reaching a final TOF value up to 35640 h(-1). The controlled experiments have revealed that the compatibility of the trifluoromethylated pyrazolyl and unprotected benzimidazolyl is crucial for the establishment of the highly active catalytic system.