3-Chloro-4-(4-chlorophenyl)-1-methyl-5-phenylpyrazole | 1448006-07-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-Chloro-4-(4-chlorophenyl)-1-methyl-5-phenylpyrazole
• CAS: 1448006-07-2
• 化学式: C₁₆H₁₂Cl₂N₂
• 分子量: 303.191
• InChiKey: AVHQFMGBXKQIJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  17.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  在 盐酸 、 sodium nitrite 、 copper(l) chloride 作用下， 以 水 为溶剂， 反应 0.5h， 生成 3-Chloro-4-(4-chlorophenyl)-1-methyl-5-phenylpyrazole
  参考文献：
  名称：

  Synthesis of Tetrasubstituted Pyrazoles through Different Cyclization Strategies; Isosteres of Imidazole Fungicides

  摘要：

  Formerly unknown 3-chloro-4,5-diaryl-1-methylpyrazoles have been prepared through two different synthesis pathways, one of which starts from 2,3-diarylacrylonitriles, the second from 3,3-dichloro-1,2-diarylpropenones. Both approaches rely on the cyclocondensation of diarylated three-carbon synthons with hydrazine derivatives and possess some unique features. One route uses a cyclization reaction, during which a chlorine atom is directly installed at the pyrazole ring that normally would be introduced in subsequent halogenation steps. The second pathway applies the Sandmeyer reaction to introduce this chloro substituent; an approach that is rarely described at the pyrazole nucleus. The obtained tetrasubstituted pyrazoles are isosteres of highly active imidazole fungicides and show good control of Uncinula necator (grape powdery mildew).

  DOI：

  10.1055/s-0033-1338433