4,5-dimethyl-2-(phenyldiazen-1-yl)-1-vinylpyrrole | 1228956-85-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: 4,5-dimethyl-2-(phenyldiazen-1-yl)-1-vinylpyrrole
• 英文别名: 2,3-dimethyl-5-phenyldiazenyl-1-vinyl-1H-pyrrole；4,5-dimethyl-2-phenylazo-1-vinylpyrrole；2,3-dimethyl-5-(phenyldiazeline)-N-vinylpyrrole；2,3-Dimethyl-5-(phenyldiazenyl)-1-vinyl-1h-pyrrole；(1-ethenyl-4,5-dimethylpyrrol-2-yl)-phenyldiazene
• CAS: 1228956-85-1
• 化学式: C₁₄H₁₅N₃
• 分子量: 225.293
• InChiKey: YSJSMHGYYFBBIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  29.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4,5-dimethyl-2-(phenyldiazen-1-yl)-1-vinylpyrrole 在 air 作用下， 以 甲苯 为溶剂， 反应 5.0h， 以23%的产率得到4-methyl-2-(phenyldiazen-1-yl)-1-vinylpyrrol-5-carbaldehyde
  参考文献：
  名称：

  Selective thermal oxidation of 2,3-dimethyl-5-(phenyldiazenyl)-1-vinyl-1H-pyrrole to the corresponding pyrrole-2-carbaldehyde: Stabilization of the pyrrole ring by phenylazo substituent

  摘要：

  DOI：

  10.1134/s1070428009100248

文献信息

• First example of autooxidation of methyl and cyclohexano groups attached to the pyrrole ring: stabilization effect of phenyldiazenyl substituents
  作者：Elena Yu. Schmidt、Elena Yu. Senotrusova、Igor A. Ushakov、Olga N. Kazheva、Oleg A. Dyachenko、Grigorii G. Alexandrov、Andrei V. Ivanova、Albina I. Mikhaleva、Boris A. Trofimov

  DOI：10.3998/ark.5550190.0011.230

  日期：——

  Methyl substituted 2-phenyldiazenyl-N-vinylpyrroles when refluxed in toluene in the airflow are unexpectedly oxidized at their methyl substituents retaining the pyrrole and N-vinyl moieties intact. The major products of the autooxidation are hydroxyalkyl derivatives (yield up to 60%), the corresponding aldehydes being formed in minor quantities (yield up to 21%). This non- typical oxidation of substituted

  甲基取代的 2-苯基二氮烯基-N-乙烯基吡咯在甲苯中在气流中回流时出乎意料地在其甲基取代基处被氧化，保持吡咯和 N-乙烯基部分完整。自动氧化的主要产物是羟烷基衍生物（产率高达 60%），相应的醛以少量形成（产率高达 21%）。取代吡咯的这种非典型氧化为苯基二氮烯基吡咯染料的官能化开辟了一种概念上的新方法。
• Metallation of N-vinylpyrroles and -indoles with Hg(OAc)2: N-vinyl vs. pyrrole nucleophilic sites
  作者：Boris A. Trofimov、Andrey V. Ivanov、Igor A. Ushakov、Elena Yu. Schmidt、Lyubov N. Sobenina、Alexander M. Vasil'tsov、Albina I. Mikhaleva

  DOI：10.1039/c2dt12393b

  日期：——

  N-Vinylpyrroles and -indoles bearing electron-withdrawing substituents at the pyrrole ring are mercurated, with 1 equivalent of Hg(OAc)2 in dry MeCN (20–80 °C), regioselectively at the vinyl group (yields are almost quantitative), while their congeners without electron-withdrawing functions are mercurated both at the N-vinyl group and the pyrrole ring.

  在吡咯环上带有吸电子取代基的N-乙烯基吡咯和-吲哚被汞化，在干燥的MeCN（20-80°C）中具有1当量的Hg（OAc）2，在乙烯基上具有区域选择性（产率几乎是定量的），而没有吸电子功能的同类物在N-乙烯基和吡咯环上均被取代。
• The reaction of 2-arylazo-1-vinylpyrroles with trifluoroacetic anhydride: unexpected formation of N-aryl-2,2,2-trifluoroacetamides and conjugated polymers
  作者：Elena Yu. Schmidt、Igor A. Ushakov、Nadezhda V. Zorina、Albina I. Mikhaleva、Boris A. Trofimov

  DOI：10.1016/j.mencom.2011.01.015

  日期：2011.1

  2-Arylazo-1-vinylpyrroles under the action of trifluoroacetic anhydride (CH2Cl2 or benzene, –5–0 °C, 1 h) form N-aryl-2,2,2-trifluoroacetamides along with conjugated (electroconducting and paramagnetic) polymers.

  2-芳基-1-乙烯基吡咯在三氟乙酸酐（CH2Cl2或苯，–5–0°C，1小时）的作用下与共轭（导电和顺磁性）聚合物一起形成N-芳基-2,2,2-三氟乙酰胺。
• Selective thermal oxidation of 2,3-dimethyl-5-(phenyldiazenyl)-1-vinyl-1H-pyrrole to the corresponding pyrrole-2-carbaldehyde: Stabilization of the pyrrole ring by phenylazo substituent
  作者：B. A. Trofimov、E. Yu. Shmidt、E. Yu. Senotrusova、I. A. Ushakov、A. I. Mikhaleva

  DOI：10.1134/s1070428009100248

  日期：2009.10