1-(4-甲基苯基)-1H-吡唑-4-甲腈 | 712-72-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 1-(4-甲基苯基)-1H-吡唑-4-甲腈
• 中文别名: 1-对甲苯基-1H-吡唑-4-腈
• 英文名称: 1-(4-methylphenyl)-1H-pyrazole-4-carbonitrile
• 英文别名: 1-p-Tolyl-pyrazol-4-carbonitril；1-p-tolyl-1H-pyrazole-4-carbonitrile；1-(p-Tolyl)-1H-pyrazole-4-carbonitrile；1-(4-methylphenyl)pyrazole-4-carbonitrile
• CAS: 712-72-1
• 化学式: C₁₁H₉N₃
• 分子量: 183.213
• InChiKey: ORTQEQIPPNZDNS-UHFFFAOYSA-N

物化性质

• 熔点：
  128-130℃

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  41.6
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2933199090

反应信息

• 作为产物：
  描述：

  (2E)-3-(二甲基氨基)-2-甲酰基丙烯腈 、 对甲基苯肼 在 盐酸 作用下， 以 乙醇 为溶剂， 反应 0.5h， 以81%的产率得到1-(4-甲基苯基)-1H-吡唑-4-甲腈
  参考文献：
  名称：

  Cyanoacetaldehyde ? New synthetic applications of an old compound syntheses with nitriles, XCI

  摘要：

  Various reactions of cyanoacetaldehyde (1), freshly prepared by ozonization of (E)-1,4-dicyano-2-butene or allylcyanide, are described. Thus, conversion of 1 with anilines gave beta-phenylaminoacrylonitriles 2a-e. Reaction of 1 with hydrazines led to the corresponding hydrazones 3a-e, which could be cyclized under alkaline conditions to 5-aminopyrazoles 4a-d. An aldol-type condensation product 5a could be obtained by reaction of 1 with sodiumphenoxide. Treatment of 1 with dimethylformamide-dimethylacetal led to the formation of (E)-3-dimethylamino-2-formylpropenenitrile (6), a very useful synthon in synthetic chemistry. For the determination of the structure of 6 the method of steady state differential NOEs was used. Reaction of 6 with hydrazines gave 1-substituted-4-cyanopyrazoles 7a-k.

  DOI：

  10.1007/bf00808679

文献信息

• Unveiling Potent Photooxidation Behavior of Catalytic Photoreductants
  作者：Karina Targos、Oliver P. Williams、Zachary K. Wickens

  DOI：10.1021/jacs.1c00399

  日期：2021.3.24

  We describe a photocatalytic system that reveals latent photooxidant behavior from one of the most reducing conventional photoredox catalysts, N-phenylphenothiazine (PTH). This aerobic photochemical reaction engages difficult to oxidize feedstocks, such as benzene, in C(sp2)–N coupling reactions through direct oxidation. Mechanistic studies are consistent with activation of PTH via photooxidation and

  我们描述了一种光催化系统，该系统揭示了最具还原性的传统光氧化还原催化剂之一N-苯基吩噻嗪 ( PTH ) 的潜在光氧化行为。这种有氧光化学反应通过直接氧化在 C(sp 2 )-N 偶联反应中参与难以氧化的原料，如苯。机理研究与通过光氧化激活PTH和路易斯酸助催化剂清除在该过程中不可避免地形成的抑制剂一致。
• Cyanoacetaldehyde ? New synthetic applications of an old compound syntheses with nitriles, XCI
  作者：Madhukar Jachak、Ulrike Krie�mann、Martin Mittelbach、Hans Junek

  DOI：10.1007/bf00808679

  日期：1993.2

  Various reactions of cyanoacetaldehyde (1), freshly prepared by ozonization of (E)-1,4-dicyano-2-butene or allylcyanide, are described. Thus, conversion of 1 with anilines gave beta-phenylaminoacrylonitriles 2a-e. Reaction of 1 with hydrazines led to the corresponding hydrazones 3a-e, which could be cyclized under alkaline conditions to 5-aminopyrazoles 4a-d. An aldol-type condensation product 5a could be obtained by reaction of 1 with sodiumphenoxide. Treatment of 1 with dimethylformamide-dimethylacetal led to the formation of (E)-3-dimethylamino-2-formylpropenenitrile (6), a very useful synthon in synthetic chemistry. For the determination of the structure of 6 the method of steady state differential NOEs was used. Reaction of 6 with hydrazines gave 1-substituted-4-cyanopyrazoles 7a-k.