5-(2-Cyanoethyl)-2,4-dimethyloxazole | 146331-20-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(2-Cyanoethyl)-2,4-dimethyloxazole
• 英文别名: 2,4-Dimethyl-5-oxazolepropanenitrile；3-(2,4-dimethyl-1,3-oxazol-5-yl)propanenitrile
• CAS: 146331-20-6
• 化学式: C₈H₁₀N₂O
• 分子量: 150.18
• InChiKey: QOGXHXMGECLFRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-酮基已腈 在 吡啶 、 sodium hydroxide 、 硫酸羟胺 、 水 、 乙酰氯 作用下， 反应 12.0h， 生成 5-(2-Cyanoethyl)-2,4-dimethyloxazole
  参考文献：
  名称：

  Synthesis of 6-substituted 2-(N-acetylamino)pyridines and 2-aminopyridines by cyclization of 5-oximinoalkanenitriles

  摘要：

  Oxime derivatives of 5-oxoalkanenitriles (C6 chain or longer) were cyclized in most cases with a combination of AcCl and Ac2O, or Ac2O and HCl to 6-substituted 2-(N-acetylamino)pyridines. hydrolysis gave the corresponding 2-aminopyridines in overall yields of 40-65 %, with the exception of pyridine 3e. Oxime derivatives of 5-oxopentanenitriles did not cyclize but gave glutaronitriles instead. In some experiments with 5-oximinohexanenitrile(1a),2,4-dimethyl-5-(2-cyanoethyl)oxazole (9)was detected in addition to the main product, 2-(N-acetylamino)-6-methylpyridine(2a). Formation of these compounds can be explained on the basis of a common intermediate 7 formed through rearrangement of the O-acetylated 5-oximinohexanenitrile (4).

  DOI：

  10.1021/jo00056a021