4,4-Dichloro-3,5-diphenyl-4H-pyrazole | 71989-82-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4,4-Dichloro-3,5-diphenyl-4H-pyrazole
• 英文别名: 4,4-dichloro-3,5-diphenylpyrazole
• CAS: 71989-82-7
• 化学式: C₁₅H₁₀Cl₂N₂
• 分子量: 289.164
• InChiKey: OFNGXVKCOBFSER-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  24.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,4-Dichloro-3,5-diphenyl-4H-pyrazole 在 palladium on activated charcoal 、 三氟乙酸 氢气 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 4.0h， 生成 (1α,4α,4aα,7aα)-2,3,4,4a,5,6,7,7a-Octahydro-8,8-dichloro-1,4-diphenyl-1,4-methano-1H-cyclopentapyridazine
  参考文献：
  名称：

  4-Halo-4H-pyrazoles: Cycloaddition with Cyclopentadiene to Azoalkanes of the 2,3-Diazabicyclo[2.2.1]hept-2-ene Type versus Electrophilic Addition with Cyclopentene

  摘要：

  The acid-catalyzed reactions of the 4-halogen-substituted 4H-pyrazoles 3 with cyclopentadiene and cyclopentene in methylene chloride have been examined. The 4,4-dichloro-3,5-diphenyl-4H-pyrazole (3a) cycloadded quantitatively with cyclopentadiene to the gem-dichloro-substituted azoalkane 4a of the 2,3-diazabicyclo[2.2.1]hept-2-ene type, whose structure was established by X-ray analysis. The azoalkane 4a was catalytically hydrogenated to the azoalkane 6 with reduced C=C double bond and the relatively persistent (toward autoxidation) hydrazine 7 with reduced C=C and N=N double bonds. The cycloaddition of 4-chloro-4-methyl-3,5-diphenyl-4H-pyrazole (3b) with cyclopentadiene gave the azoalkane anti-4b in high yield and diastereoselectivity. The azoalkanes 4a,b and 6 were reluctant toward photolysis and thermolysis and the expected housanes were not produced under these conditions. The acid-catalyzed reaction of the 4-bromo-substituted 4H-pyrazoles 3c-e with cyclopentadiene gave, instead of the desired cycloadducts, complex product mixtures. In the presence of acid, the 4H-pyrazoles 3 gave with cyclopentene the 2-(alpha-halocyclopentyl)-substituted 2H-pyrazoles 5 as products of electrophilic addition.

  DOI：

  10.1021/jo00102a036
• 作为产物：
  描述：

  3,5-diphenylpyrazole 在 次氯酸叔丁酯 作用下， 以 二氯甲烷 为溶剂， 以76%的产率得到4,4-Dichloro-3,5-diphenyl-4H-pyrazole
  参考文献：
  名称：

  Halogenation of N-oxygenated pyrazoles. Preparation of N-oxygenated 4-halopyrazole and 4,4-dihalo-4H-pyrazole derivatives

  摘要：

  DOI：

  10.1021/jo01289a017

文献信息

• HANSEN J. F.; KIM Y. I.; GRISWOLD L. J.; HOELLE G. W.; TAYLOR D. L.; VIET+, J. ORG. CHEM., 1980, 45, NO 1, 76-80
  作者：HANSEN J. F.、 KIM Y. I.、 GRISWOLD L. J.、 HOELLE G. W.、 TAYLOR D. L.、 VIET+

  DOI：——

  日期：——
• Adam Waldemar, Ammon Horst, Nau Werner M., Peters Karl, J. Org. Chem, 59 (1994) N 23, S 7067- 7071
  作者：Adam Waldemar, Ammon Horst, Nau Werner M., Peters Karl

  DOI：——

  日期：——