3-methyl-2-(N-methylanilino)-4-oxohexanenitrile

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 3-methyl-2-(N-methylanilino)-4-oxohexanenitrile
• 化学式: C₁₄H₁₈N₂O
• 分子量: 230.31
• InChiKey: VTVFBFBJYMCTJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.63
• 重原子数：
  17.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  44.1
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  2-(甲基(苯基)氨基)乙腈 在 四氯化钛 、 N,N-二异丙基乙胺 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 3.75h， 生成 3-methyl-2-(N-methylanilino)-4-oxohexanenitrile
  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

• 2-(N-methylanilino)-2-phenylsulfanylacetonitrile, a reagent tested for electrophilic, nucleophilic and radical reactions
  作者：Chih-Cheng Chen、Same-Ting Chen、Tsung-Hsun Chuang、Jim-Min Fang

  DOI：10.1039/p19940002217

  日期：——

  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.