4-diazo-1-(p-tolyl)-3-trifluoromethylpyrazolin-5-one | 1384431-58-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-diazo-1-(p-tolyl)-3-trifluoromethylpyrazolin-5-one
• 英文别名: 4-Diazonio-2-(4-methylphenyl)-5-(trifluoromethyl)pyrazol-3-olate；4-diazonio-2-(4-methylphenyl)-5-(trifluoromethyl)pyrazol-3-olate
• CAS: 1384431-58-6
• 化学式: C₁₁H₇F₃N₄O
• 分子量: 268.198
• InChiKey: HBQNNCKVUZAXIJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  69
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  对二甲苯 、 4-diazo-1-(p-tolyl)-3-trifluoromethylpyrazolin-5-one 在 dirhodium tetraacetate 作用下， 反应 4.0h， 以68%的产率得到4-(2,5-dimethylphenyl)-1-(p-tolyl)-3-(trifluoromethyl)-1H-pyrazol-5-ol
  参考文献：
  名称：

  The Rh2(OAc)4-catalyzed reactions of 3-trifluoromethyl-4-diazopyrazolinones with aromatic compounds

  摘要：

  The C H insertion reactions of 3-trifluoromethy1-4-diazopyrazolinones 1 with benzene and its derivatives catalyzed by Rh-2(OAc)(4) were studied. It was found that the Csp(2)-H insertion products were obtained in good yields when anisole or xylene etc. was used, while the aromatic compounds with electronic-withdrawing groups, such as fluorobenzene, chlorobenzene, and benzonitrile, did not react with the diazo compounds 1. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.12.077
• 作为产物：
  描述：

  2-p-Tolyl-5-trifluoromethyl-2,4-dihydro-pyrazol-3-one 在 1,1,2,2-tetrafluoro-2-(1,1,2,2-tetrafluoro-2-iodoethoxy)-ethanesulfonyl azide 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以89%的产率得到4-diazo-1-(p-tolyl)-3-trifluoromethylpyrazolin-5-one
  参考文献：
  名称：

  1,3-Dipolar cycloaddition reaction of 3-trifluoromethyl-4-diazopyrazolinones with acetylenedicarboxylates

  摘要：

  Refluxing of 3-trifluoromethyl-4-diazopyrazolinones 1 with dimethyl acetylenedicarboxylates 2 in toluene for 48 h afforded trifluoromethyl-substituted pyrazolo [1,5-d][1,2,4]triazin-7-ones, which resulted from the [3+2] dipolar cycloaddition followed by a rearrangement of the initially produced spiro 3H-pyrazole adducts. However, when 1 was heated to 160 degrees C in dichlorobenzene (o-DCB) for 8 h, it lost nitrogen and reacted with 2 to give 3-trifluoromethyl furo[2,3-c]pyrazoles. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.05.062

文献信息

• The Rh2(OAc)4-catalyzed reactions of 3-trifluoromethyl-4-diazopyrazolinones with aromatic compounds
  作者：Huafang Fan、Zhenhua Zhang、Xinjin Li、Jingwei Zhao、Jinming Gao、Shizheng Zhu

  DOI：10.1016/j.tet.2012.12.077

  日期：2013.2

  The C H insertion reactions of 3-trifluoromethy1-4-diazopyrazolinones 1 with benzene and its derivatives catalyzed by Rh-2(OAc)(4) were studied. It was found that the Csp(2)-H insertion products were obtained in good yields when anisole or xylene etc. was used, while the aromatic compounds with electronic-withdrawing groups, such as fluorobenzene, chlorobenzene, and benzonitrile, did not react with the diazo compounds 1. (C) 2013 Elsevier Ltd. All rights reserved.
• 1,3-Dipolar cycloaddition reaction of 3-trifluoromethyl-4-diazopyrazolinones with acetylenedicarboxylates
  作者：Zhenhua Zhang、Xiaowei Wang、Song Tao、Shizheng Zhu

  DOI：10.1016/j.tet.2012.05.062

  日期：2012.7

  Refluxing of 3-trifluoromethyl-4-diazopyrazolinones 1 with dimethyl acetylenedicarboxylates 2 in toluene for 48 h afforded trifluoromethyl-substituted pyrazolo [1,5-d][1,2,4]triazin-7-ones, which resulted from the [3+2] dipolar cycloaddition followed by a rearrangement of the initially produced spiro 3H-pyrazole adducts. However, when 1 was heated to 160 degrees C in dichlorobenzene (o-DCB) for 8 h, it lost nitrogen and reacted with 2 to give 3-trifluoromethyl furo[2,3-c]pyrazoles. (C) 2012 Elsevier Ltd. All rights reserved.