4,4-dimethyl-2,5-diphenyl-2,4-dihydro-3H-pyrazol-3-one | 115977-58-7

• 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: 4,4-dimethyl-2,5-diphenyl-2,4-dihydro-3H-pyrazol-3-one
• 英文别名: 4,4-dimethyl-2,5-diphenylpyrazol-3-one
• CAS: 115977-58-7
• 化学式: C₁₇H₁₆N₂O
• 分子量: 264.327
• InChiKey: MLXLAGQCIWFXMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.46
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  32.67
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4,4-dimethyl-2,5-diphenyl-2,4-dihydro-3H-pyrazol-3-one 在 劳森试剂 作用下， 以 甲苯 为溶剂， 反应 2.0h， 生成 4,4-Dimethyl-2,5-diphenyl-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：

  在 叔丁基过氧化氢 、 氧气 作用下， 以 癸烷 、 乙腈 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 10.0h， 以46%的产率得到4,4-dimethyl-2,5-diphenyl-2,4-dihydro-3H-pyrazol-3-one
  参考文献：
  名称：

  吡唑啉酮和吡唑啉的发散组装的不饱和的无金属环化†

  摘要：

  提出了在无金属条件下，β，γ-不饱和的氧化环化，用于吡唑啉酮和吡唑啉的发散组装。通过控制反应气氛实现了这种多样化的合成策略。当在N 2下进行反应时，通过5- exo- trig环化获得许多吡唑啉。而当反应在O 2下进行时，通过C C双键的氧化裂解获得了多种官能化的吡唑啉酮。

  DOI：

  10.1039/c9cc04039k

文献信息

• Henning, Hans-Georg; Koppe, Angelika, Zeitschrift fur Chemie, 1987, vol. 27, # 10, p. 367 - 368
  作者：Henning, Hans-Georg、Koppe, Angelika

  DOI：——

  日期：——