1-methyl-3,5-bis(difluoromethyl)-1H-pyrazole | 1571942-52-3

• 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-methyl-3,5-bis(difluoromethyl)-1H-pyrazole
• 英文别名: 3,5-bis(difluoromethyl)-1-methyl-1H-pyrazole；N-methyl-3,5-bis(difluoromethyl)pyrazole；3,5-bis(difluoromethyl)-1-methylpyrazole
• CAS: 1571942-52-3
• 化学式: C₆H₆F₄N₂
• 分子量: 182.121
• InChiKey: BHUCBSRSWDMNIM-UHFFFAOYSA-N

物化性质

• 沸点：
  189.2±35.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-methyl-3,5-bis(difluoromethyl)-4-pyrazolecarboxylic acid ethyl ester 在 copper(I) oxide 、 1,10-菲罗啉 、 水 、 sodium hydroxide 作用下， 以 N-甲基吡咯烷酮 、 喹啉 、 乙醇 、 水 为溶剂， 反应 17.0h， 生成 1-methyl-3,5-bis(difluoromethyl)-1H-pyrazole
  参考文献：
  名称：

  A New Synthesis and Process Development of Bis(fluoroalkyl)pyrazoles As Novel Agrophores

  摘要：

  The synthesis of 3,5-bis(fluoroalkyl)-pyrazoles as novel agrophores is described. Commercially available fluoroacetoacetates are treated with BF3-activated TFEDMA affording in a straightforward one-pot sequence pyrazole carboxylates in good yields and with excellent regioselectivity. The carboxylate intermediates have been converted into the corresponding pyrazolic acids and submitted to decarboxylation, affording valuable building blocks for the design of novel bioactive ingredients. The found process is suitable for scale up and preparation of compounds in kilogram quantity.

  DOI：

  10.1021/op500102h

文献信息

• A Major Advance in the Synthesis of Fluoroalkyl Pyrazoles: Tuneable Regioselectivity and Broad Substitution Patterns
  作者：Etienne Schmitt、Armen Panossian、Jean-Pierre Vors、Christian Funke、Norbert Lui、Sergiy Pazenok、Frédéric R. Leroux

  DOI：10.1002/chem.201601621

  日期：2016.8.1

  A novel approach towards highly functionalized fluoroalkyl pyrazoles was developed by using fluoroalkyl amino reagents in combination with a variety of fluorinated ketimines. Tuneable introduction of fluoroalkyl groups in the 3‐ and 5‐positions was possible by using vinamidinium intermediates or the corresponding enamino ketones after hydrolysis. These high‐value building blocks can give rise to a

  通过结合使用氟代烷基氨基试剂和各种氟化酮亚胺，开发了一种高度官能化的氟代烷基吡唑的新方法。在水解后使用乙烯基ami中间体或相应的烯胺酮，可以在3位和5位上引入氟烷基基团。这些高价值的组成部分可以为生物活性筛选和在各种生命科学领域中发现新的杂环生物活性成分提供大量类似物。
• [EN] PROCESS FOR PREPARING 3,5-BIS(HALOALKYL)PYRAZOLE DERIVATIVES FROM α,α-DIHALOAMINES AND KETIMINES<br/>[FR] PROCÉDÉ DE PRÉPARATION DE DÉRIVÉS DE 3,5-BIS(HALOALKYL)PYRAZOLE À PARTIR D'Α,Α-DIHALOAMINES ET DE CÉTIMINES
  申请人：BAYER CROPSCIENCE AG

  公开号：WO2015144578A1

  公开（公告）日：2015-10-01

  Process for preparine3,5-bis(haloalkyl)pyrazolederivatives from a,a-dihaloamines and ketimines The present invention relates to a novel process for preparing 3,5-bis(haloalkyl)pyrazole derivatives from a,a-dihaloamines and ketimines. Intermedaites used in the process are also claimed.

  从α,α-二卤胺和酮亚胺制备3,5-双(卤代烷基)吡唑衍生物的过程。本发明涉及一种从α,α-二卤胺和酮亚胺制备3,5-双(卤代烷基)吡唑衍生物的新方法。该过程中使用的中间体也被要求。
• Insecticidal 4-phenyl-1H-pyrazoles
  申请人：Werner Stefan

  公开号：US20110190365A1

  公开（公告）日：2011-08-04

  The present invention relates to novel 4-phenyl-1H-pyrazoles and their use as insecticides and/or parasiticides and also to processes for their preparation and to compositions comprising such phenylpyrazoles.

  本发明涉及新型的4-苯基-1H-吡唑并将其用作杀虫剂和/或驱虫剂，还涉及其制备方法以及包含这些苯基吡唑的组合物。
• [EN] PYRIDINE DERIVATIVES AND THEIR USE FOR TREATING HIV INFECTION<br/>[FR] DÉRIVÉS DE PYRIDINE ET LEUR UTILISATION POUR LE TRAITEMENT D'UNE INFECTION PAR LE VIH
  申请人：GILEAD SCIENCES INC

  公开号：WO2019161017A1

  公开（公告）日：2019-08-22

  The invention provides compounds having Formula (I): (I) or a pharmaceutically acceptable salt thereof, as well as pharmaceutical compositions comprising the same, processes for their preparation, and methods of treating and preventing HIV infection by their administration.

  该发明提供具有式（I）的化合物：（I）或其药学上可接受的盐，以及包含它们的药物组合物，其制备方法，以及通过它们的给药治疗和预防HIV感染的方法。
• [EN] PROCEDURE FOR THE DECARBOXYLATION OF 3,5-BIS(HALOALKYL)-PYRAZOLE-4-CARBOXYLIC ACID DERIVATIVES<br/>[FR] PROCÉDURE DE DÉCARBOXYLATION DE DÉRIVÉS D'ACIDE 3,5-BIS(HALOALKYL)-PYRAZOLE-4-CARBOXYLIQUE
  申请人：BAYER CROPSCIENCE AG

  公开号：WO2014033164A1

  公开（公告）日：2014-03-06

  A new process for the preparation of 3,5-bis(haloalkyl)-pyrazole derivatives of the general formula (I), is described, resulting from the reaction of 3,5-bis(haloalkyl)-pyrazole-4-carboxylic acid derivatives of the general formula (IIa) with a copper compound and a base at elevated temperature wherein R1 is selected from H, C1-12-alkyl, C3-8-cycloalkyl, C6-18-aryl, C7-19-arylalkyl or C7-19-alkylaryl, CH2CN, CH2CX3, CH2COOH, CH2COO(C1-12)-alkyl, and X is independently of each other F, Cl, Br, I; R2 and R3 are selected independently of each other from C1-C6-haloalkyl.

  介绍了一种新的制备通式为（I）的3,5-双（卤代烷基）-吡唑衍生物的方法，其结果是将通式为（IIa）的3,5-双（卤代烷基）-吡唑-4-羧酸衍生物与铜化合物和碱在高温下反应，其中R1从H，C1-12-烷基，C3-8-环烷基，C6-18-芳基，C7-19-芳基烷基或C7-19-烷基芳基，CH2CN，CH2CX3，CH2COOH，CH2COO（C1-12）-烷基中选择，而X独立地为F、Cl、Br、I；R2和R3独立地从C1-C6卤代烷基中选择。