N-methyl-3-difluoromethyl-5-trifluoromethyl-4-pyrazolecarboxylic acid ethyl ester | 1448776-14-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-methyl-3-difluoromethyl-5-trifluoromethyl-4-pyrazolecarboxylic acid ethyl ester
• 英文别名: ethyl 1-methyl-3-difluoromethyl-5-trifluoromethyl-1H-pyrazole-4-carboxylate；1-Methyl-3-(difluoromethyl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid ethyl ester；ethyl 3-(difluoromethyl)-1-methyl-5-(trifluoromethyl)pyrazole-4-carboxylate
• CAS: 1448776-14-4
• 化学式: C₉H₉F₅N₂O₂
• 分子量: 272.175
• InChiKey: GRZMUVRFHFLPFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-methyl-3-difluoromethyl-5-trifluoromethyl-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 3-(difluoromethyl)-1-methyl-5-(trifluoromethyl)-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
• 作为产物：
  描述：

  ethyl 2-(2,2,2-trifluoroacetyl)-3-(dimethylamino)-4,4-difluorobut-2-enoate 、 甲基肼 以 乙腈 为溶剂， 反应 24.0h， 生成 N-methyl-3-difluoromethyl-5-trifluoromethyl-4-pyrazolecarboxylic acid ethyl ester
  参考文献：
  名称：

  旧试剂的新生命：氟烷基氨基试剂是合成多种氟化吡唑的有效工具

  摘要：

  在此，我们描述了区域选择性制备 3,5-双（氟烷基）吡唑的第一种实用方法。从市售的氟乙酰乙酸酯开始，并使用（四氟乙基）二甲胺作为方便的 CF2H 转移试剂，这种简单的一锅法以良好的收率和出色的区域选择性提供了高度取代的吡唑。此外，这些羧酸酯中间体被转化为相应的吡唑酸，这是设计新型生物活性成分的宝贵基础。

  DOI：

  10.1002/ejoc.201300561

文献信息

• METHOD FOR PRODUCING 3,5-BIS(FLUOROALKYL)-PYRAZOL-4-CARBOXYLIC ACID DERIVATIVES AND 3,5-BIS(FLUOROALKYL)-PYRAZOLES
  申请人：BAYER CROPSCIENCE AG

  公开号：US20150011779A1

  公开（公告）日：2015-01-08

  The present invention relates to novel 3,5-bis(fluoroalkyl)pyrazole-4-carboxylic acid derivatives and to a process for preparing 3,5-bis(fluoroalkyl)pyrazole-4-carboxylic acid derivatives and 3,5-bis(fluoroalkyl)pyrazoles.

  本发明涉及新型3,5-双(氟烷基)吡唑-4-羧酸衍生物以及制备3,5-双(氟烷基)吡唑-4-羧酸衍生物和3,5-双(氟烷基)吡唑的方法。
• [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。
• Procedure for the decarboxylation of 3,5-bis(haloalkyl)-pyrazole-4-carboxylic acid derivatives
  申请人：BAYER CROPSCIENCE AG

  公开号：US09145370B2

  公开（公告）日：2015-09-29

  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.

  介绍了一种制备通式（I）的3,5-双（卤代烷基）-吡唑衍生物的新工艺，该工艺是通过将通式（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而得到的。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独立地选择为F、Cl、Br、I；R2和R3独立地选择为C1-C6-卤代烷基。
• PROCEDURE FOR THE DECARBOXYLATION OF 3,5-BIS(HALOALKYL)-PYRAZOLE-4-CARBOXYLIC ACID DERIVATIVES
  申请人：BAYER CROPSCIENCE AG

  公开号：US20150225350A1

  公开（公告）日：2015-08-13

  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 (Ha) with a copper compound and a base at elevated temperature wherein R 1 is selected from H, C 1-12 -alkyl, C 3-8 -cycloalkyl, C 6-18 -aryl, C 7-19 -arylalkyl or C 7-19 -alkylaryl, CH 2 CN, CH 2 CX 3 , CH 2 COOH, CH 2 COO(C 1-12 )-alkyl, and X is independently of each other F, Cl, Br, I; R 2 and R 3 are selected independently of each other from C 1 -C 6 -haloalkyl.

  本文描述了一种制备通式（I）的3,5-双（卤代烷基）-吡唑衍生物的新工艺，该工艺是通过在升高温度下将通式（Ha）的3,5-双（卤代烷基）-吡唑-4-羧酸衍生物与铜化合物和碱反应而得到的。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，X独立选择为F、Cl、Br、I；R2和R3独立选择为C1-C6-卤代烷基。
• Method for producing 3,5-bis(fluoroalkyl)-pyrazol-4-carboxylic acid derivatives and 3,5-bis(fluoroalkyl)-pyrazoles
  申请人：BAYER CROPSCIENCE AG

  公开号：US09309202B2

  公开（公告）日：2016-04-12

  The present invention relates to novel 3,5-bis(fluoroalkyl)pyrazole-4-carboxylic acid derivatives and to a process for preparing 3,5-bis(fluoroalkyl)pyrazole-4-carboxylic acid derivatives and 3,5-bis(fluoroalkyl)pyrazoles.

  本发明涉及新型的3,5-双(氟烷基)吡唑-4-羧酸衍生物，以及制备3,5-双(氟烷基)吡唑-4-羧酸衍生物和3,5-双(氟烷基)吡唑的方法。