5-(2,4-difluorophenyl)-3-(trifluoromethyl)-1H-pyrazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(2,4-difluorophenyl)-3-(trifluoromethyl)-1H-pyrazole
• 英文别名: 3-(2,4-difluorophenyl)-5-(trifluoromethyl)-1H-pyrazole
• 化学式: C₁₀H₅F₅N₂
• 分子量: 248.155
• InChiKey: RDDVKBITZMMEJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 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：
  28.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5-(2,4-difluorophenyl)-3-(trifluoromethyl)-1H-pyrazole 在 硝酸 、 乙酸酐 、 溶剂黄146 作用下， 以100%的产率得到3-(2,4-Difluoro-phenyl)-1-nitro-5-trifluoromethyl-1H-pyrazole
  参考文献：
  名称：

  3-Trifluoromethyl-4-nitro-5-arylpyrazoles are novel KATP channel agonists

  摘要：

  This communication describes the discovery and synthesis of a series of 3-trifluoromethyl-4-nitro-5-arylpyrazoles as potent K-ATP channel agonists. The most potent compound reported is ca. 100-fold more potent than diazoxide and exhibits selectivity for the SUR 1 K-ATP channel subtype. The 4-nitro substitutent on the pyrazole ring was required for activity, and limited SAR suggests that the de-protonated pyrazole maybe the active species. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.10.066
• 作为产物：
  描述：

  2,4-二氟苯甲醛 、 diethyl (3,3,3-trifluoro-2-(2-tosylhydrazono)propyl)phosphonate 在 sodium hexamethyldisilazane 作用下， 反应 3.0h， 以65%的产率得到5-(2,4-difluorophenyl)-3-(trifluoromethyl)-1H-pyrazole
  参考文献：
  名称：

  3-Trifluoromethyl-4-nitro-5-arylpyrazoles are novel KATP channel agonists

  摘要：

  This communication describes the discovery and synthesis of a series of 3-trifluoromethyl-4-nitro-5-arylpyrazoles as potent K-ATP channel agonists. The most potent compound reported is ca. 100-fold more potent than diazoxide and exhibits selectivity for the SUR 1 K-ATP channel subtype. The 4-nitro substitutent on the pyrazole ring was required for activity, and limited SAR suggests that the de-protonated pyrazole maybe the active species. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2003.10.066

文献信息

• Herbicidal substituted aryl-haloalkylpyrazoles
  申请人：Monsanto Company

  公开号：US05489571A1

  公开（公告）日：1996-02-06

  The invention herein relates to certain substituted-arylpyrazole compounds, herbicidal compositions containing same, herbicidal methods of use and processes for preparing said compounds.

  本发明涉及某些取代芳基吡唑化合物、含有该化合物的除草剂组合物、使用该化合物的除草方法以及制备该化合物的过程。
• Process for the preparation of substituted
  申请人：Monsanto Company

  公开号：US05530126A1

  公开（公告）日：1996-06-25

  The disclosure herein relates to a process for the preparation of compounds according to Formula N ##STR1## which comprises using a compound of Formula M ##STR2## as starting material for alkylation to said compounds of Formula N in an inert solvent at temperatures within the range of 0.degree.-200.degree. C. wherein R.sub.1 is C.sub.1-5 alkyl; R.sub.2 is C.sub.1-5 haloalkyl; R.sub.3 is halogen; R.sub.5 is hydrogen or halogen; q is 0-2; R.sub.28 and R.sub.30 are independently an alkyl, alkenyl or alkynyl radical having up to 5 carbon atoms or said radicals substituted with a ##STR3## radical; X is O, S(O).sub.m, NR.sub.19 or CR.sub.20 R.sub.21 ; Y is O, S(O).sub.m or NR.sub.22 ; m is 0-2 and R.sub.13 and R.sub.19 -R.sub.22 are hydrogen or an R.sub.28 member. The above compounds are useful as herbicides.

  本文披露了一种制备公式N的化合物的过程##STR1##，该过程包括在惰性溶剂中使用公式M的化合物##STR2##作为烷基化反应的起始物，制备公式N的化合物，反应温度在0℃至200℃范围内，其中R1为C1-5烷基；R2为C1-5卤代烷基；R3为卤素；R5为氢或卤素；q为0-2；R28和R30分别是具有最多5个碳原子的烷基，烯基或炔基基团，或者是被##STR3##基团取代的该基团；X为O，S（O）m，NR19或CR20R21；Y为O，S（O）m或NR22；m为0-2，R13和R19-R22为氢或R28成员。上述化合物可用作除草剂。
• Herbicidal benzoxazinone- and benzothiazinone-substituted pyrazoles
  申请人：Monsanto Company

  公开号：US05281571A1

  公开（公告）日：1994-01-25

  The invention herein relates to titled compounds having the structure ##STR1## wherein the R.sub.1 -(R.sub.4).sub.n members are as defined in the claims. Characteristic features of these compounds are the haloalkyl R.sub.2 radical and cyclization of two R.sub.4 members at the meta and para positions of the phenyl ring to form a substituted benzoxazinone ring fused to the phenyl or benzthiazinone ring. Such compounds are useful as active ingredients in herbicidal compositions to control undesirable weeds in various crops.

  本发明涉及具有以下结构的称为化合物：##STR1## 其中R.sub.1 - (R.sub.4) .sub.n成员如权利要求中所定义。这些化合物的特征特点是卤代烷基R.sub.2基团和两个R.sub.4成员在苯环的间位和对位上环化，形成与苯环或苯并噻唑酮环融合的取代苯并噁唑酮环。这些化合物可用作除草剂组合物中的活性成分，以控制各种作物中的不良杂草。
• Benzoyl derivatives
  申请人：MONSANTO COMPANY

  公开号：EP0791571A1

  公开（公告）日：1997-08-27

  The invention herein relates to certain substituted-arylpyrazole compounds, herbicidal compositions containing same, herbicidal methods of use and processes for preparing said compounds.

  本发明涉及某些取代芳基吡唑化合物、含有这些化合物的除草组合物、除草使用方法以及制备上述化合物的工艺。
• HERBICIDAL SUBSTITUTED ARYL-HALOALKYLPYRAZOLES
  申请人：MONSANTO COMPANY

  公开号：EP0553307A1

  公开（公告）日：1993-08-04