2-(4-Methylanilino)-2-(4-methylsulfanylphenyl)acetonitrile | 461443-92-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-(4-Methylanilino)-2-(4-methylsulfanylphenyl)acetonitrile
• CAS: 461443-92-5
• 化学式: C₁₆H₁₆N₂S
• 分子量: 268.382
• InChiKey: VGYYMPTZTOZLSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-Methylanilino)-2-(4-methylsulfanylphenyl)acetonitrile 在 potassium hydroxide 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 3.75h， 生成 4-amino-5-(4-(methylthio)phenyl)-3-phenyl-1-p-tolyl-1H-pyrrol-2(5H)-one
  参考文献：
  名称：

  Approaches to the Construction of Substituted 4-Amino-1H-pyrrol-2(5H)-ones

  摘要：

  Fully substituted 4-aminopyrrolones are easily accessed via simple routes starting from imines, ketones, or alpha-bromophenyl acetonitriles. Imines were reacted with KCN/NH4Cl in aqueous ethanol to produce alpha-arylamino benzyl cyanides. On the other hand, ketones were transformed to the desired alpha-amino nitriles using a modified Strecker reaction. Then, alpha-amino nitrile precursors were allowed to react with a suitable acyl halide to produce the corresponding amides. Further treatment of these amides with ethanolic KOH converted them to highly substituted 4-amino-1H-pyrrol-2(5H)-one derivatives in moderate to excellent yields.

  DOI：

  10.1021/jo3004309
• 作为产物：
  描述：

  potassium cyanide 、 N-(4-methylphenyl)-1-(4-methylsulfanylphenyl)methanimine 在 十六烷基三甲基溴化铵 、 氯化铵 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 2-(4-Methylanilino)-2-(4-methylsulfanylphenyl)acetonitrile
  参考文献：
  名称：

  Approaches to the Construction of Substituted 4-Amino-1H-pyrrol-2(5H)-ones

  摘要：

  Fully substituted 4-aminopyrrolones are easily accessed via simple routes starting from imines, ketones, or alpha-bromophenyl acetonitriles. Imines were reacted with KCN/NH4Cl in aqueous ethanol to produce alpha-arylamino benzyl cyanides. On the other hand, ketones were transformed to the desired alpha-amino nitriles using a modified Strecker reaction. Then, alpha-amino nitrile precursors were allowed to react with a suitable acyl halide to produce the corresponding amides. Further treatment of these amides with ethanolic KOH converted them to highly substituted 4-amino-1H-pyrrol-2(5H)-one derivatives in moderate to excellent yields.

  DOI：

  10.1021/jo3004309

文献信息

• Silica-bonded S-sulfonic acid: an efficient and recyclable solid acid catalyst for the three-component synthesis of α-amino nitriles
  作者：Khodabakhsh Niknam、Dariush Saberi、Maryam Nouri Sefat

  DOI：10.1016/j.tetlet.2010.03.093

  日期：2010.6

  Silica-bonded S-sulfonic acid (SBSSA) is employed as a recyclable catalyst for the synthesis of α-amino nitriles. These syntheses were performed via a one-pot three-component condensation of aldehydes, amines, and trimethylsilyl cyanide under mild reaction conditions at room temperature.

  二氧化硅键合的S-磺酸（SBSSA）被用作可再循环的催化剂，用于合成α-氨基腈。这些合成是通过在室温下温和的反应条件下，通过一锅三组分缩合醛，胺和三甲基甲硅烷基氰化物进行的。