1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoroacetylpyrazole | 617699-98-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoroacetylpyrazole
• 英文别名: 1-[1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-1H-pyrazole-4-yl]-2,2,2-trifluoroethanone；1-[1-[2,6-dichloro-4-(trifluoromethyl)phenyl]pyrazol-4-yl]-2,2,2-trifluoroethanone
• CAS: 617699-98-6
• 化学式: C₁₂H₄Cl₂F₆N₂O
• 分子量: 377.073
• InChiKey: MYHZJMQLBUWGAT-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：
  0.17
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoroacetylpyrazole 在 sodium tetrahydroborate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 6.0h， 生成 1-(2,6-dichloro-3-iodo-4-trifluoromethylphenyl)-4-[1-hydroxy-(2,2,2-trifluoroethyl)]iodopyrazole
  参考文献：
  名称：

  Synthesis of a Tritium-Labeled, Fipronil-Based, Highly Potent, Photoaffinity Probe for the GABA Receptor

  摘要：

  3-{4-[1-(2,6-Dichloro-4-trifluoromethylphenyl)pyrazolo]}-3-(trifluoromethyl)diazirine is a fipronil-based (i.e. fiprole), high-affinity probe for the GABA receptor. For synthesis of the tritium-labeled version of this trifluoromethyldiazirinylfiprole ([H-3]TDF) the required intermediate, 3-{4-[1-(2,6-dichloro-3-iodo-4-trifluoromethylphenyl)-5-iodopyrazolo]}-3-(trifluoromethyl)diazirine, was prepared in 10 steps from pyrazole and 3,5-dichloro-4-fluorobenzotrifluoride. One of the key transformations was lithiation and subsequent iodination of the 4-(2,2,2-trifluoro-1-hydroxyethyl)pyrazole intermediate. The last step involved reduction of the diiodofiprole with tritium, Pd/C, and triethylamine in ethyl acetate and afforded [H-3]TDF with a specific activity of 15 Ci/mmol and 99% radiopurity.

  DOI：

  10.1021/jo034520z
• 作为产物：
  描述：

  1-(2,6-二氯-4-三氟甲基-苯基)吡唑 在 正丁基锂 、 溴 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 1.25h， 生成 1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoroacetylpyrazole
  参考文献：
  名称：

  Fipronil-based photoaffinity probe for Drosophila and human β3 GABA receptors

  摘要：

  Modification of the major insecticide fipronil (1) by replacing three pyrazole substituents (hydrogen for both cyano and amino and trifluoromethyldiazirinyl for trifluoromethylsulfinyl) gives a candidate photoaffinity probe (3) of high potency (IC50 2-28 nM) in blocking the chloride channel of Drosophila and human beta3 GABA receptors. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00604-7

文献信息

• Synthesis of a Tritium-Labeled, Fipronil-Based, Highly Potent, Photoaffinity Probe for the GABA Receptor
  作者：Robert E. Sammelson、John E. Casida

  DOI：10.1021/jo034520z

  日期：2003.10.1

  3-4-[1-(2,6-Dichloro-4-trifluoromethylphenyl)pyrazolo]}-3-(trifluoromethyl)diazirine is a fipronil-based (i.e. fiprole), high-affinity probe for the GABA receptor. For synthesis of the tritium-labeled version of this trifluoromethyldiazirinylfiprole ([H-3]TDF) the required intermediate, 3-4-[1-(2,6-dichloro-3-iodo-4-trifluoromethylphenyl)-5-iodopyrazolo]}-3-(trifluoromethyl)diazirine, was prepared in 10 steps from pyrazole and 3,5-dichloro-4-fluorobenzotrifluoride. One of the key transformations was lithiation and subsequent iodination of the 4-(2,2,2-trifluoro-1-hydroxyethyl)pyrazole intermediate. The last step involved reduction of the diiodofiprole with tritium, Pd/C, and triethylamine in ethyl acetate and afforded [H-3]TDF with a specific activity of 15 Ci/mmol and 99% radiopurity.
• Fipronil-based photoaffinity probe for Drosophila and human β3 GABA receptors
  作者：Nilantha S. Sirisoma、Gurpreet S. Ratra、Motohiro Tomizawa、John E. Casida

  DOI：10.1016/s0960-894x(01)00604-7

  日期：2001.11

  Modification of the major insecticide fipronil (1) by replacing three pyrazole substituents (hydrogen for both cyano and amino and trifluoromethyldiazirinyl for trifluoromethylsulfinyl) gives a candidate photoaffinity probe (3) of high potency (IC50 2-28 nM) in blocking the chloride channel of Drosophila and human beta3 GABA receptors. (C) 2001 Elsevier Science Ltd. All rights reserved.