3-methyl-2-(2-oxazolyl)butanenitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-methyl-2-(2-oxazolyl)butanenitrile
• 英文别名: 3-Methyl-2-(1,3-oxazol-2-yl)butanenitrile
• 化学式: C₈H₁₀N₂O
• 分子量: 150.18
• InChiKey: VJEFWBNWEAIGIE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 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：

  异戊腈 、 2-甲硫基噁唑 在 正丁基锂 、 四甲基乙二胺 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 以33%的产率得到3-methyl-2-(2-oxazolyl)butanenitrile
  参考文献：
  名称：

  Monosubstituted Oxazoles. 1. Synthesis of 5-Substituted Oxazoles by Directed Alkylation

  摘要：

  A general method is presented for synthesis of 2-(methylthio)-5-substituted oxazoles 2. Deprotonation of the readily available 2-(methylthio)oxazole (1) with n-BuLi occurs smoothly in the presence of TMEDA and regiospecifically at C5. The organometallic la added rapidly to aldehydes and other electrophiles to provide 5-substituted-2-(methylthio)oxazoles in very good to excellent yields. Reductive removal of the MeS group gave the desired 5-monosubstituted oxazoles 3 in good yield.

  DOI：

  10.1021/jo971410h

文献信息

• Monosubstituted Oxazoles. 1. Synthesis of 5-Substituted Oxazoles by Directed Alkylation
  作者：Cynthia M. Shafer、Tadeusz F. Molinski

  DOI：10.1021/jo971410h

  日期：1998.2.1

  A general method is presented for synthesis of 2-(methylthio)-5-substituted oxazoles 2. Deprotonation of the readily available 2-(methylthio)oxazole (1) with n-BuLi occurs smoothly in the presence of TMEDA and regiospecifically at C5. The organometallic la added rapidly to aldehydes and other electrophiles to provide 5-substituted-2-(methylthio)oxazoles in very good to excellent yields. Reductive removal of the MeS group gave the desired 5-monosubstituted oxazoles 3 in good yield.