2-(N-methylanilino)butanenitrile | 88017-50-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(N-methylanilino)butanenitrile
• 英文别名: 2-(methyl(phenyl)amino)butanenitrile；Butanenitrile, 2-(methylphenylamino)-
• CAS: 88017-50-9
• 化学式: C₁₁H₁₄N₂
• 分子量: 174.246
• InChiKey: DQDARQCWASUUAB-UHFFFAOYSA-N

物化性质

• 沸点：
  288.3±23.0 °C(Predicted)
• 密度：
  1.020±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(N-methylanilino)butanenitrile 生成 N-甲基-N-苯基丙酰胺
  参考文献：
  名称：

  CHUANG, TSUNG-HSUN;YANG, CHAU-CHEN;CHANG, CHIH-JUNG;FANG, JIM-MIN, SYNLETT.,(1990) N2, C. 733-734

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(甲基(苯基)氨基)乙腈 在 copper(l) iodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 生成 2-(N-methylanilino)butanenitrile
  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

• Ag-Catalyzed Cyanomethylation of Amines Using Nitromethane as a C₁ Source
  作者：Takuya Takashima、Hamdiye Ece、Taiga Yurino、Takeshi Ohkuma

  DOI：10.1021/acs.orglett.3c02256

  日期：2023.8.18

  A new methodology to afford α-amino nitriles through oxidative cyanomethylation of amines using nitromethane as the methylene source in the presence of Me3SiCN without the addition of an external oxidant was developed. A catalytic amount of AgCN and a stoichiometric amount of LiBF4 cooperatively promoted the transformation. A wide variety of the amines, including both aromatic compounds and aliphatic

  开发了一种在 Me 3 SiCN存在下，在不添加外部氧化剂的情况下，使用硝基甲烷作为亚甲基源，通过胺的氧化氰甲基化来提供 α-氨基腈的新方法。催化量的AgCN和化学计量量的LiBF 4协同促进转化。多种胺，包括芳香族化合物和脂肪族胺，在氧化条件下不稳定，适用于该反应。
• 1,4-Dicarbonyl-Verbindungen durch Michael-Addition deprotonierter Aminonitrile an α,β-ungesättigte Carbonyl-Verbindungen
  作者：Hubertus Ahlbrecht、Hans-Michael Kompter

  DOI：10.1055/s-1983-30458

  日期：——
• CHUANG, TSUNG-HSUN;YANG, CHAU-CHEN;CHANG, CHIH-JUNG;FANG, JIM-MIN, SYNLETT.,(1990) N2, C. 733-734
  作者：CHUANG, TSUNG-HSUN、YANG, CHAU-CHEN、CHANG, CHIH-JUNG、FANG, JIM-MIN

  DOI：——

  日期：——
• 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.