1-(2,6-dichloro-4-trifluoromethylphenyl)-4-iodopyrazole | 617699-97-5

• 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-iodopyrazole
• 英文别名: 1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-4-iodo-1H-pyrazole；1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-iodopyrazole
• CAS: 617699-97-5
• 化学式: C₁₀H₄Cl₂F₃IN₂
• 分子量: 406.961
• InChiKey: QZYQAIOYFUXUSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 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：
  17.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2,6-dichloro-4-trifluoromethylphenyl)-4-iodopyrazole 在 sodium tetrahydroborate 、 盐酸羟胺 、 异丙基氯化镁 、 戴斯-马丁氧化剂 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 吡啶 、 乙醇 、 二氯甲烷 为溶剂， 反应 23.0h， 生成 1-(2,6-dichloro-3-iodo-4-trifluoromethylphenyl)-5-iodo-4-(trifluoroacetyl)pyrazole oxime
  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：

  4-碘吡唑 、 1,3-二氯-2-碘-5-(三氟甲基)苯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以99%的产率得到1-(2,6-dichloro-4-trifluoromethylphenyl)-4-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

文献信息

• NOVEL COMPOUNDS FOR CONTROLLING ARTHROPODS
  申请人：BAYER CROPSCIENCE AKTIENGESELLSCHAFT

  公开号：US20160278379A1

  公开（公告）日：2016-09-29

  The invention relates inter alia to compounds of the general formula (I) in which the A 1 -A 4 , T, n, W, Q, R 1 and B 1 -B 4 radicals are each as defined in the description. Also described are processes for preparing the compounds of the formula (I). The inventive compounds are especially suitable for controlling insects, arachnids and nematodes in agriculture, and ectoparasites in veterinary medicine.

  该发明涉及一般式（I）化合物，其中A1-A4，T，n，W，Q，R1和B1-B4基团如描述中所定义。还描述了制备公式（I）化合物的过程。这些创新的化合物特别适用于农业中控制昆虫，蜘蛛和线虫，以及兽医学中的外寄生虫。
• [EN] ANTIPARASITIC COMBINATIONS<br/>[FR] COMBINAISONS ANTIPARASITAIRES
  申请人：BAYER ANIMAL HEALTH GMBH

  公开号：WO2016174052A1

  公开（公告）日：2016-11-03

  The invention relates to antiparasitic combinations comprising inter alia to compounds of the general formula (I) in which the A1-A4, T, n, W, Q, R1 and B1 -B4 radicals are each as defined in the description. Also described are processes for preparing the compounds of the formula (I). The combinations further comprise ectoparasiciticides, anthelmintics or anti-protozoal agents. The combinations are especially suitable for controlling ectoparasites, helminths and/or protozoa on or in animals.

  本发明涉及抗寄生虫组合物，包括一般式（I）中的化合物，其中A1-A4，T，n，W，Q，R1和B1-B4基团在描述中各自定义。还描述了制备式（I）化合物的方法。该组合物还包括杀虫剂、驱虫药或抗原虫剂。该组合物特别适用于控制动物体内或体外的外寄生虫、蠕虫和/或原虫。
• Compounds for controlling arthropods
  申请人：BAYER CROPSCIENCE AKTIENGESELLSCHAFT

  公开号：US10150737B2

  公开（公告）日：2018-12-11

  The invention relates inter alia to compounds of the general formula (I) in which the A1-A4, T, n, W, Q, R1 and B1-B4 radicals are each as defined in the description. Also described are processes for preparing the compounds of the formula (I). The inventive compounds are especially suitable for controlling insects, arachnids and nematodes in agriculture, and ectoparasites in veterinary medicine.

  本发明主要涉及通式 (I) 的化合物 其中 A1-A4、T、n、W、Q、R1 和 B1-B4 各自由基如描述中所定义。还描述了制备式（I）化合物的工艺。本发明化合物尤其适用于控制农业中的昆虫、蛛形纲动物和线虫，以及兽医中的体外寄生虫。
• [EN] NITROGEN-CONTAINING HETEROCYCLIC DERIVATIVE, AND COMPOSITION AND PHARMACEUTICAL USE THEREOF<br/>[FR] DÉRIVÉ HÉTÉROCYCLIQUE CONTENANT DE L'AZOTE, COMPOSITION ET UTILISATION PHARMACEUTIQUE DE CELUI-CI<br/>[ZH] 一种含氮杂环衍生物及其组合物和药学上的应用
  申请人：[en]TIBET HAISCO PHARMACEUTICAL CO., LTD.;[zh]西藏海思科制药有限公司

  公开号：WO2024012570A1

  公开（公告）日：2024-01-18

  一种通式(I)所述的化合物或者其立体异构体、氘代物、溶剂化物、前药、代谢产物、药学上可接受的盐或共晶，及其中间体，以及在AR相关疾病如癌症中的用途。 B-L-K (I)
• SUBSTITUIERTE BENZAMIDE ZUR BEHANDLUNG VON ARTHROPODEN
  申请人：Bayer CropScience Aktiengesellschaft

  公开号：EP3066079A1

  公开（公告）日：2016-09-14