(2E,4E)-2-(N-methylanilino)hexa-2,4-dienenitrile | 101383-72-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2E,4E)-2-(N-methylanilino)hexa-2,4-dienenitrile
• CAS: 101383-72-6
• 化学式: C₁₃H₁₄N₂
• 分子量: 198.268
• InChiKey: KRJOOVNUUMKSKG-MUFDPIBCSA-N

物化性质

• 沸点：
  329.0±34.0 °C(Predicted)
• 密度：
  1.041±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  27.03
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2E,4E)-2-(N-methylanilino)hexa-2,4-dienenitrile 在 硫酸 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 20.0h， 生成 ethyl 2,10-dimethyl-9-oxoacridine-1-carboxylate
  参考文献：
  名称：

  Use of .alpha.-anilino dienenitriles as nucleophiles in cycloadditions

  摘要：

  DOI：

  10.1021/jo00263a040
• 作为产物：
  描述：

  2-(甲基(苯基)氨基)乙腈 在 potassium tert-butylate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 1.08h， 生成 (2E,4E)-2-(N-methylanilino)hexa-2,4-dienenitrile
  参考文献：
  名称：

  2-(N-methylanilino)-2-phenylsulfanylacetonitrile, a reagent tested for electrophilic, nucleophilic and radical reactions

  摘要：

  2-(N-Methylanilino) -2-phenylsulfanylacetonitrile 1 has been readily prepared from 2-(N-methylanilino)acetonitrile and diphenyl disulfide. Alkylation of the anion of 1 with halogenoalkanes resulted in concurrent elimination of benzenethiol to give conjugated alpha-aminoalkenenitriles of 2E-configuration. Autoxidation of 1 in the presence of alkoxide ions afforded alkyl N-methyl-N-phenylcarbamates. Nucleophilic substitution of 1 with Grignard reagent or appropriate silyl compounds were promoted by Cul or Lewis acids to give varied alpha-amino nitriles. The 4-oxo-2-amino nitriles 9 obtained by condensation of 1 and titanium enolates can be considered as derivatives of 1,3-dicarbonyl compounds with the aldehyde group being activated to give an amino nitrile umpolung. When 1 was treated with tributylstannane, the corresponding amino nitrile alpha-radical was formed and the self-coupling product was isolated.

  DOI：

  10.1039/p19940002217

文献信息

• Cycloadditions of α-aminonitrile diene
  作者：Jim-Min Fang、Chau-Chen Yang

  DOI：10.1039/c39850001356

  日期：——

  Cycloadditions of 2-(N-methylanilino)hexa-2,4-dienenitrile with the dienophiles maleic anhydride, N-phenylmaleimide, benzoquinone, or dimethyl acetylenedicarboxylate led to methyldiarylamines after loss of hydrogen cyanide and oxidative aromatisation.

  2-（N-甲基苯胺基）六-2,4-二烯腈与亲二烯体马来酸酐，N-苯基马来酰亚胺，苯醌或乙炔二羧酸二甲酯的环加成反应在氰化氢损失和氧化芳构化后生成甲基二芳基胺。