4-diazo-1-phenyl-3-(trifluoromethyl)-1H-pyrazol-5(4H)-one | 1338583-24-6

• 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-phenyl-3-(trifluoromethyl)-1H-pyrazol-5(4H)-one
• 英文别名: 4-diazo-1-phenyl-3-trifluoromethylpyrazolin-5-one；1-Phenyl-3-(trifluoromethyl)-4-diazo-2-pyrazoline-5-one；4-diazonio-2-phenyl-5-(trifluoromethyl)pyrazol-3-olate
• CAS: 1338583-24-6
• 化学式: C₁₀H₅F₃N₄O
• 分子量: 254.171
• InChiKey: OGCRTLLVSKGTAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  4-diazo-1-phenyl-3-(trifluoromethyl)-1H-pyrazol-5(4H)-one 在 劳森试剂 作用下， 以 对二甲苯 为溶剂， 反应 5.0h， 以86%的产率得到4-diazo-1-phenyl-3-(trifluoromethyl)-1H-pyrazole-5(4H)-thione
  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：

  1-苯基-3-三氟甲基-1(H)-吡唑-5-酮 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-phenyl-3-(trifluoromethyl)-1H-pyrazol-5(4H)-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

• Construction of fluorinated pyrazole derivatives via a one-pot tandem C–H insertion/electrophilic fluorination reaction
  作者：Kai Zhang、Gang Zhao、Weiguo Cao

  DOI：10.1016/j.tet.2014.06.065

  日期：2014.9

  A series of 4-fluoro-pyrazole derivatives were synthesized in moderate to good yields via a one-pot tandem procedure involving an Rh2(OAc)4-catalyzed C–H insertion and an electrophilic fluorination with N-fluorobenzenesulfonimide (NFSI).

  通过一锅串联程序，包括Rh 2（OAc）4催化的C–H插入和N-氟苯磺酰亚胺（NFSI）的亲电氟化，以中等至良好的产率合成了一系列4-氟-吡唑衍生物。
• Facile synthesis of novel CF3-substituted ring-fused furo[2,3-c]pyrazoles through Rh2(OAc)4 catalyzed [3+2] cycloaddition of 4-diazo-1-phenyl-3-(trifluoromethyl)-1H-pyrazol-5(4H)-one with aromatic alkynes
  作者：Zhenhua Zhang、Jianwei Han、Shizheng Zhu

  DOI：10.1016/j.tet.2011.09.007

  日期：2011.11

  The Rh-2(OAc)(4) catalyzed [3+2] cycloaddition of 4-diazo-1-phenyl-3-(trifluoromethyl)-1H-pyrazol-5(4H)-one with aromatic alkynes was studied, and this protocol can be efficiently applied to the synthesis of the novel CF3-substituted ring-fused furo[2,3-c]pyrazoles. (C) 2011 Elsevier Ltd. All rights reserved.