1-(Azidomethyl)-4-cyano-3-phenylpyrazole | 117007-81-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(Azidomethyl)-4-cyano-3-phenylpyrazole
• 英文别名: 1-(Azidomethyl)-3-phenyl-1H-pyrazole-4-carbonitrile；1-(azidomethyl)-3-phenylpyrazole-4-carbonitrile
• CAS: 117007-81-5
• 化学式: C₁₁H₈N₆
• 分子量: 224.225
• InChiKey: HXWICAKROIAOEL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  56
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(Azidomethyl)-4-cyano-3-phenylpyrazole 以 丙酮 为溶剂， 反应 14.0h， 以60%的产率得到1-<(4-Cyano-3-phenyl-1-pyrazolyl)methyl>-5-phenyltriazole
  参考文献：
  名称：

  Azide ring-opening-ring-closure reactions and tele-substitutions in vicinal azidopyrazole-, pyrrole- and indolecarboxaldehydes

  摘要：

  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.

  DOI：

  10.1021/jo00033a039
• 作为产物：
  描述：

  5-氯-1-甲基-3-苯基-1H-吡唑-4-甲醛 在 sodium azide 作用下， 以 二甲基亚砜 为溶剂， 生成 1-(Azidomethyl)-4-cyano-3-phenylpyrazole
  参考文献：
  名称：

  5-azido-4-formylpyrazole意外的开环-闭环反应

  摘要：

  由于开环-闭环反应的结果，在与过量的叠氮化钠在二甲基亚砜（DMSO）中反应时，5-氯-4-甲酰基-1-甲基吡唑类化合物会生成1-叠氮基甲基-4-氰基吡唑类化合物。已经确定了叠氮基甲基吡唑的晶体结构。

  DOI：

  10.1039/c39880000541

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.
• An unexpected ring opening–ring closure reaction of 5-azido-4-formylpyrazole
  作者：Jan Becher、Klaus Brøndum、Niels Krake、Krystian Pluta、Ole Simonsen、Pedro Molina、Mikael Begtrup

  DOI：10.1039/c39880000541

  日期：——

  5-Chloro-4-formyl-1-methylpyrazoles give 1-azidomethyl-4-cyanopyrazoles on reaction with an excess of sodium azide in dimethyl sulphoxide (DMSO), as a result of a ring opening–ring closure reaction; the crystal structure of the azidomethylpyrazole has been determined.

  由于开环-闭环反应的结果，在与过量的叠氮化钠在二甲基亚砜（DMSO）中反应时，5-氯-4-甲酰基-1-甲基吡唑类化合物会生成1-叠氮基甲基-4-氰基吡唑类化合物。已经确定了叠氮基甲基吡唑的晶体结构。