5-benzyl-4,4-dimethyl-2-phenyl-2,4-dihydro-pyrazol-3-one | 24979-44-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑啉类
• 英文名称: 5-benzyl-4,4-dimethyl-2-phenyl-2,4-dihydro-pyrazol-3-one
• CAS: 24979-44-0
• 化学式: C₁₈H₁₈N₂O
• 分子量: 278.354
• InChiKey: UGBOWIZMLXHOMA-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  5-benzyl-4,4-dimethyl-2-phenyl-2,4-dihydro-pyrazol-3-one 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 5-Benzyl-4,4-dimethyl-2-phenyl-2,4-dihydro-pyrazole-3-thione
  参考文献：
  名称：

  Synthesis and Structure-Activity Relationships of Miticidal 4,5-Dihydropyrazole-5-thiones

  摘要：

  A series of novel 4,5-dihydropyrazole-5-thiones (DHPs) was synthesised by treating the corresponding dihydropyrazolones with Lawesson's reagent and evaluated for miticidal activity against two-spotted spider mites (Tetranychus urticae Koch). Of these, 3-(4-chlorophenyl)-4,4-dimethyl-1-phenyl-4, 5-dihydropyrazole-5-thione, 3-(4-chlorophenyl)-4-ethyl-4-methyl-1-phenyl-4,5-dihydropyrazole-5-thione, 3-(4-chlorophenyl)-1-phenyl-4,5-dihydropyrazole-5-thione-4-spirocyclopentane and 4,4-dimethyl-1-phenyl-3-(4-trifluoromethyl-phenyl)-4,5-dihydropyrazole-5-thione were highly active (pEC(50) > 4 . 0) and were more effective than the miticide dicofol (pEC(50) = 3 . 879), which has traditionally been used for the control of phytophagous mites. Structure-activity relationship (SAR) studies were performed on each position of the pyrazole ring of DHPs. The results indicated that the unsubstituted phenyl, 4-substituted phenyl and thioxo groups on the 1-, 3- and 5-positions of DHPs respectively were required for activity. Quantitative SAR studies using physicochemical parameters of substituents and the capacity factor k' as a hydrophobicity index suggested that: (a) the activities of all types of DHPs examined were mainly dominated by hydrophobicity, (b) the bulkiness of 4-substituents of the 3-phenyl ring favoured the activity and (c) the log k' optimum for all DHPs was 1 . 675, equivalent to a log P-ow value of c. 5 . 0.

  DOI：

  10.1002/(sici)1096-9063(199610)48:2<165::aid-ps455>3.0.co;2-z
• 作为产物：
  描述：

  2-Methyl-2-phenacetyl-propionsaeure-aethylester 、 苯肼 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 16.0h， 生成 5-benzyl-4,4-dimethyl-2-phenyl-2,4-dihydro-pyrazol-3-one
  参考文献：
  名称：

  Synthesis and Structure-Activity Relationships of Miticidal 4,5-Dihydropyrazole-5-thiones

  摘要：

  A series of novel 4,5-dihydropyrazole-5-thiones (DHPs) was synthesised by treating the corresponding dihydropyrazolones with Lawesson's reagent and evaluated for miticidal activity against two-spotted spider mites (Tetranychus urticae Koch). Of these, 3-(4-chlorophenyl)-4,4-dimethyl-1-phenyl-4, 5-dihydropyrazole-5-thione, 3-(4-chlorophenyl)-4-ethyl-4-methyl-1-phenyl-4,5-dihydropyrazole-5-thione, 3-(4-chlorophenyl)-1-phenyl-4,5-dihydropyrazole-5-thione-4-spirocyclopentane and 4,4-dimethyl-1-phenyl-3-(4-trifluoromethyl-phenyl)-4,5-dihydropyrazole-5-thione were highly active (pEC(50) > 4 . 0) and were more effective than the miticide dicofol (pEC(50) = 3 . 879), which has traditionally been used for the control of phytophagous mites. Structure-activity relationship (SAR) studies were performed on each position of the pyrazole ring of DHPs. The results indicated that the unsubstituted phenyl, 4-substituted phenyl and thioxo groups on the 1-, 3- and 5-positions of DHPs respectively were required for activity. Quantitative SAR studies using physicochemical parameters of substituents and the capacity factor k' as a hydrophobicity index suggested that: (a) the activities of all types of DHPs examined were mainly dominated by hydrophobicity, (b) the bulkiness of 4-substituents of the 3-phenyl ring favoured the activity and (c) the log k' optimum for all DHPs was 1 . 675, equivalent to a log P-ow value of c. 5 . 0.

  DOI：

  10.1002/(sici)1096-9063(199610)48:2<165::aid-ps455>3.0.co;2-z