4-(5-Chloro-2-pyridinyl)-4,5-dihydro-N-ethoxycarbonyl-3-(4-fluorophenyl)-N-(4-trifluoromethoxyphenyl)-1H-pyrazole-1-carboxamide | 145834-52-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-(5-Chloro-2-pyridinyl)-4,5-dihydro-N-ethoxycarbonyl-3-(4-fluorophenyl)-N-(4-trifluoromethoxyphenyl)-1H-pyrazole-1-carboxamide
• 英文别名: ethyl N-[4-(5-chloropyridin-2-yl)-5-(4-fluorophenyl)-3,4-dihydropyrazole-2-carbonyl]-N-[4-(trifluoromethoxy)phenyl]carbamate
• CAS: 145834-52-2
• 化学式: C₂₅H₁₉ClF₄N₄O₄
• 分子量: 550.897
• InChiKey: LIPSFJZVORILLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  38
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  84.3
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  4-(5-chloro-2-pyridinyl)-4,5-dihydro-3-(4-fluorophenyl)-N-(4-trifluoromethoxyphenyl)-1H-pyrazole-1-carboxamide 、 氯甲酸乙酯 在 sodium;hydride 、 正己烷 、 四氢呋喃 、 ice 、 氯化铵 、 乙醚 、 magnesium sulfate 、 丙酮 作用下， 反应 2.0h， 以to obtain 660 mg of the title compound as white crystals melting at 159.5°-161° C. (60 percent yield)的产率得到4-(5-Chloro-2-pyridinyl)-4,5-dihydro-N-ethoxycarbonyl-3-(4-fluorophenyl)-N-(4-trifluoromethoxyphenyl)-1H-pyrazole-1-carboxamide
  参考文献：
  名称：

  3,4,N-trisubstituted-4,5-dihydro-1H-pyrazole-1-carboxamides and their

  摘要：

  制备了3,4,N-三芳基-4,5-二氢-1H-吡唑烷-1-羧酰胺化合物，其中4位是芳基基团，可以是选择性取代的吡啶基、嘧啶基、吡嗪基、吡咯嗪基或喹啉基团，3位和N位是芳基基团，可以是选择性取代的苯基、吡啶基、嘧啶基、吡嗪基、吡咯嗪基或喹啉基团，例如N-(4-氯苯基)-4,5-二氢-3-(4-氟苯基)-4-(5-三氟甲基-2-吡啶基)-1H-吡唑烷-1-羧酰胺，具有杀虫功效。1,2-二芳基乙酮化合物通过与双(二甲氨基)甲烷反应，转化为1,2-二芳基-2-丙烯-1-酮化合物，然后通过与肼反应，转化为3,4-二芳基-4,5-二氢-1H-吡唑烷化合物，最后通过与芳基异氰酸酯反应，转化为具有杀虫功效的目标化合物。

  公开号：

  US05250532A1

文献信息

• 3,4,N-Trisubstituted-4,5-dihydro-1H-pyrazole-1-carboxamides and their use as insecticides
  申请人：DOWELANCO

  公开号：EP0508469A1

  公开（公告）日：1992-10-14

  3,4,N-Triaryl-4,5-dihydro-1H-pyrazole-1-carboxamide compounds having an aryl moiety in the 4-position that is an optionally substituted pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, or quinolinyl moiety and aryl moieties in the 3-position and the N-position that are optionally substituted phenyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, or quinolinyl moieties, such as N-(4-chlorophenyl)-4,5-dihydro-3-(4-fluorophenyl)-4-(5-trifluoromethyl-2-pyridinyl)-1H-pyrazole-1-carboxamide, were prepared and found to possess insecticidal utility. 1,2-Diarylethanone compounds were converted to 1,2-diaryl-2-propen-1-one compounds by treatment with bis(dimethylamino)methane, the 1,2-diaryl-2-propen-1-one compounds were converted to 3,4-diaryl-4,5-dihydro-1H-pyrazole compounds by treatment with hydrazine, and the 3,4-diaryl-4,5-dihydro-1H-pyrazole compounds were converted to the insecticidal subject compounds by treatment with an aryl isocyanate.

  3,4,N-三芳基-4,5-二氢-1H-吡唑-1-甲酰胺化合物，其 4 位上的芳基是任选取代的吡啶基、嘧啶基、哒嗪基、吡嗪基或喹啉基，3 位和 N 位上的芳基是任选取代的苯基、制备了 N-(4-氯苯基)-4,5-二氢-3-(4-氟苯基)-4-(5-三氟甲基-2-吡啶基)-1H-吡唑-1-甲酰胺等具有杀虫功效的化合物。1,2-Diarylethanone 化合物经双（二甲基氨基）甲烷处理后转化为 1,2-diaryl-2-propen-1-one 化合物，1,2-diaryl-2-propen-1-one 化合物经肼处理后转化为 3,4-diaryl-4,5-dihydro-1H-pyrazole 化合物，3,4-diaryl-4,5-dihydro-1H-pyrazole 化合物经芳基异氰酸酯处理后转化为杀虫主题化合物。
• US5250532A
  申请人：——

  公开号：US5250532A

  公开（公告）日：1993-10-05
• 3,4,N-trisubstituted-4,5-dihydro-1H-pyrazole-1-carboxamides and their
  申请人：DowElanco

  公开号：US05250532A1

  公开（公告）日：1993-10-05

  3,4,N-triaryl-4,5-dihydro-1H-pyrazole-1-carboxamide compounds having an aryl moiety in the 4-position that is an optionally substituted pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, or quinolinyl moiety and aryl moieties in the 3-position and the N-position that are optionally substituted phenyl, pyridinyl, pyrimidinyl, pyridazinyl, pyrazinyl, or quinolinyl moieties, such as N-(4-chlorophenyl)-4,5- -dihydro-3-(4-fluorophenyl)-4-(5-trifluoromethyl-2- -pyridinyl)-1H-pyrazole-1-carboxamide, were prepared and found to possess insecticidal utility. 1,2-Diarylethanone compounds were converted to 1,2-diaryl-2-propen-1-one compounds by treatment with bis(dimethylamino)methane, the 1,2-diaryl-2-propen-1-one compounds were converted to 3,4-diaryl-4,5-dihydro-1H-pyrazole compounds by treatment with hydrazine, and the 3,4-diaryl-4,5-dihydro-1H-pyrazole compounds were converted to the insecticidal subject compounds by treatment with an aryl isocyanate.

  制备了一种在4位上具有取代的吡啶基、嘧啶基、吡嗪基、吡咯嗪基或喹啉基芳基部分，以及在3位和N位上具有取代的苯基、吡啶基、嘧啶基、吡嗪基、吡咯嗪基或喹啉基芳基部分的3,4,N-三芳基-4,5-二氢-1H-吡唑-1-羧酰胺化合物，例如N-(4-氯苯基)-4,5-二氢-3-(4-氟苯基)-4-(5-三氟甲基-2-吡啶基)-1H-吡唑-1-羧酰胺，并发现具有杀虫效用。将1,2-二芳基乙酮化合物通过与双(二甲氨基)甲烷反应转化为1,2-二芳基-2-丙烯-1-酮化合物，再通过与肼反应转化为3,4-二芳基-4,5-二氢-1H-吡唑化合物，最后通过与芳基异氰酸酯反应转化为所述杀虫活性化合物。