4-Cyano-5-hydroxy-1,3-diphenylpyrazole | 139347-68-5

• 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-Cyano-5-hydroxy-1,3-diphenylpyrazole
• CAS: 139347-68-5
• 化学式: C₁₆H₁₁N₃O
• 分子量: 261.283
• InChiKey: WGTRINPKDFFENE-UHFFFAOYSA-N

物化性质

• 沸点：
  514.9±50.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.12
• 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：
  0.0
• 拓扑面积：
  61.84
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  5-叠氮基-1,3-二苯基-1H-吡唑-4-甲醛 以 xylene 为溶剂， 生成 4-Cyano-5-hydroxy-1,3-diphenylpyrazole
  参考文献：
  名称：

  L'abbe, Gerrit; Dyall, Leonard; Meersman, Kathleen, Journal of the Chemical Society. Perkin transactions II, 1994, # 12, p. 2401 - 2406

  摘要：

  DOI：

文献信息

• Azide ring-opening-ring-closure reactions and tele-substitutions in vicinal azidopyrazole-, pyrrole- and indolecarboxaldehydes
  作者：Jan Becher、Per Lauge Joergensen、Krystian Pluta、Niels J. Krake、Birgitte Falt-Hansen

  DOI：10.1021/jo00033a039

  日期：1992.3

  5-Chloro-1-methylpyrazole-4-carboxaldehydes 1 react with excess sodium azide in dimethyl sulfoxide to produce a mixture of 1-azidomethyl-4-cyanopyrazoles 2 and 4-cyano-5-hydroxy-1-methylpyrazoles 3. Application of this reaction to the corresponding 5-chloro-1-phenylpyrazole-4-carboxaldehydes 5 gave 4-cyano-5-hydroxy-1-phenyl-pyrazoles 7 as the sole products in high yields. Likewise, 2-aryl-5-chloro-1-methylpyrrole-3,4-dicarboxaldehydes 9 rearranged to 2-aryl-4-cyano-5-hydroxy-1-methylpyrrole-3-carboxaldehydes 10 in high yields. In the indole series, treatment of 1-aryl-2-chloroindole-3-carboxaldehydes 11 with NaN3 yielded a mixture of 1-aryl-3-cyano-2(3H)-indolones 13 and 1-aryl-5-azido-3-cyanoindoles 12, both products resulting from a ring-opening-ring-closure reaction with concomitant nucleophilic tele-substitution at the 5-position of the indole ring.