1-(2,6-dichloro-3-iodo-4-trifluoromethylphenyl)-4-[1-hydroxy-(2,2,2-trifluoroethyl)]-5-iodopyrazole | 617700-03-5

• 分子结构分类: 有机化合物
• 英文名称: 1-(2,6-dichloro-3-iodo-4-trifluoromethylphenyl)-4-[1-hydroxy-(2,2,2-trifluoroethyl)]-5-iodopyrazole
• 英文别名: 1-[1-[2,6-Dichloro-3-iodo-4-(trifluoromethyl)phenyl]-5-iodopyrazol-4-yl]-2,2,2-trifluoroethanol
• CAS: 617700-03-5
• 化学式: C₁₂H₄Cl₂F₆I₂N₂O
• 分子量: 630.882
• InChiKey: SONSWGSHAXZDLJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  25
• 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：
  38
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1-(2,6-dichloro-3-iodo-4-trifluoromethylphenyl)-4-[1-hydroxy-(2,2,2-trifluoroethyl)]-5-iodopyrazole 在 palladium on activated charcoal 4-二甲氨基吡啶 、 盐酸羟胺 、 氨 、 氢气 、 碘 、 戴斯-马丁氧化剂 、 三乙胺 作用下， 以 吡啶 、 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， -78.0~50.0 ℃ 、104.36 kPa 条件下， 反应 22.0h， 生成 3-{4-[1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazolo]}-3-(trifluoromethyl)diazirine
  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-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)]-5-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