1-苯基-3-五氟乙基-4-三氟甲基-5-氟吡唑 | 121807-33-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-苯基-3-五氟乙基-4-三氟甲基-5-氟吡唑
• 英文名称: 1-phenyl-3-pentafluoroethyl-4-trifluoromethyl-5-fluoropyrazole
• 英文别名: 5-Fluoro-3-pentafluoroethyl-4-trifluoromethyl-1-phenylpyrazole；5-Fluoro-3-pentafluoroethyl-1-phenyl-4-trifluoromethyl-1H-pyrazole；5-fluoro-3-(1,1,2,2,2-pentafluoroethyl)-1-phenyl-4-(trifluoromethyl)pyrazole
• CAS: 121807-33-8
• 化学式: C₁₂H₅F₉N₂
• 分子量: 348.171
• InChiKey: WOEYQBUTVGYDLU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-苯基-3-五氟乙基-4-三氟甲基-5-氟吡唑 在 氨 、 三乙胺 作用下， 以 乙二醇二甲醚 为溶剂， 反应 10.0h， 以71%的产率得到5-(1,1,2,2,2-pentafluoroethyl)-2-phenyl-4-(trifluoromethyl)pyrazol-3-amine
  参考文献：
  名称：

  5-Fluoro-substituted pyrazoles

  摘要：

  A preparative method was developed for the synthesis of 5-fluoro-substituted pyrazoles by the reaction of fluoroolefins with substituted hydrazines in the presence of triethylamine. The fluorine atom at the C5 position of the pyrazoles obtained is readily substituted by O-, N-, and S-nucleophiles with the formation of 5-alkoxy-, amino-, mercapto-substituted fluoroalkylpyrazoles.

  DOI：

  10.1007/bf00958848
• 作为产物：
  描述：

  2-(Trifluoromethyl)-1,1,1,4,4,5,5,5-octafluoropentan-3-one 在 三乙胺 作用下， 反应 0.5h， 生成 1-苯基-3-五氟乙基-4-三氟甲基-5-氟吡唑
  参考文献：
  名称：

  5-Fluoro-substituted pyrazoles

  摘要：

  A preparative method was developed for the synthesis of 5-fluoro-substituted pyrazoles by the reaction of fluoroolefins with substituted hydrazines in the presence of triethylamine. The fluorine atom at the C5 position of the pyrazoles obtained is readily substituted by O-, N-, and S-nucleophiles with the formation of 5-alkoxy-, amino-, mercapto-substituted fluoroalkylpyrazoles.

  DOI：

  10.1007/bf00958848

文献信息

• [EN] PROCESS FOR THE PREPARATION OF 5-FLUORO-1H-PYRAZOLES STARTING FROM HEXAFLUOROPROPENE<br/>[FR] PROCÉDÉ DE PRÉPARATION DE 5-FLUORO-1H-PYRAZOLES À PARTIR D'HEXAFLUOROPROPÈNE
  申请人：BAYER CROPSCIENCE AG

  公开号：WO2015181139A1

  公开（公告）日：2015-12-03

  A new process for the preparation of 5-fluoro-1H-pyrazoles of the general formula (I)as described herein and further reactions with this compound.

  这里描述了一种制备通式（I）中5-氟-1H-吡唑的新工艺，以及与该化合物的进一步反应。
• [EN] PROCESS FOR THE PREPARATION OF 5-FLUORO-1H-PYRAZOLES<br/>[FR] PROCÉDÉ POUR LA PRÉPARATION DE 5-FLUORO-1H-PYRAZOLES
  申请人：BAYER CROPSCIENCE AG

  公开号：WO2015078846A1

  公开（公告）日：2015-06-04

  A new process for the preparation of 5-fluoro-1H-pyrazoles of the general formula (I) as described herein, resulting from the reaction of an olefin with hydrazine in the presence of water and a base.

  这里描述了一种制备通式（I）中5-氟-1H-吡唑的新工艺，该工艺是通过烯烃与肼在水和碱的存在下发生反应而得到的。
• [EN] PROCESS FOR THE PREPARATION OF 5-FLUORO-1H-PYRAZOLES<br/>[FR] PROCÉDÉ DE PRÉPARATION DE 5-FLUORO-1H-PYRAZOLES
  申请人：BAYER CROPSCIENCE AG

  公开号：WO2015078847A1

  公开（公告）日：2015-06-04

  A new process for the preparation of 5-fluoro-1H-pyrazoles of the general formula (I) as described herein comprising reacting an olefin with an hydrazine.

  本文描述了一种制备通式（I）中的5-氟-1H-吡唑的新工艺，包括将烯烃与肼反应。
• PROCESS FOR THE PREPARATION OF 5-FLUORO-1H-PYRAZOLES
  申请人：BAYER CROPSCIENE AG

  公开号：US20150152062A1

  公开（公告）日：2015-06-04

  A new process for the preparation of 5-fluoro-1H-pyrazoles of the general formula (I) is described, resulting from the reaction of an olefin of the general formula (II) with hydrazines of the formula (III) R 1 —NH—NH 2 (III), wherein R 1 is selected from C 1 -C 6 alkyl, C 5 -C 10 aryl; R 2 is a trihalomethyl moiety with at least one fluorine atom; and R 3 is selected from C 1 -C 5 haloalkyl, CF 3 , C 2 F 5 , C 3 F 7 , CF 2 CF 2 Cl, CFClCF 3 , in the presence of water and a base.

  描述了一种制备通式（I）的5-氟-1H-吡唑的新工艺，其来源于通式（II）的烯烃与通式（III）R1—NH—NH2（III）的肼的反应，其中R1选自C1-C6烷基，C5-C10芳基；R2是至少含有一个氟原子的三卤甲基基团；R3选自C1-C5卤代烷基，CF3，C2F5，C3F7，CF2CF2Cl，CFClCF3，在水和碱的存在下。
• Synthesis of fluorinated N-arylpyrazoles with perfluoro-2-methyl-2-pentene and arylhydrazines
  作者：Ki-Whan Chi、Sung-Jun Kim、Tae-Ho Park、Yurii V. Gatilov、Irina Yu. Bagryanskaya、Georgii G. Furin

  DOI：10.1016/s0022-1139(99)00079-2

  日期：1999.8

  Reactions of arylhydrazines (phenyl, 2-nitrophenyl, 4-nitrophenyl, 2,4-dinitrophenyl, pentafluorophenyl, 4-trifluoromethyl-2,3,5,6-tetrafluorophenylhydrazine or 4,4'-dihydrazinooctafluorobiphenyl) with perfluoro-2-methyl-2-pentene in the presence of triethylamine have effectively produced 1-aryl-perfluoro-3-ethyl-4-methylpyrazole and 1-aryl-perfluoro-5-ethyl-4-methylpyrazole in various ratios depending on the reaction conditions and arylhydrazine used. Syn- and anti-aminoimines which might be the intermediates for pyrazoles have been isolated under appropriate conditions. The routes of formation for these products and the role of triethylamine have been discussed. The reaction of perfluoro-2-methyl-2-pentene with phenylhydrazine has been investigated in detail. The structure of 3-fluoro-5-pentafluoroethyl-1-phenyl-4-trifluoromethylpyrazole has been elucidated by X-ray crystallography. (C) 1999 Elsevier Science S.A. All rights reserved.