2-(4'-Pyrrolidinobutyl)-5-ethoxyoxazole | 140662-72-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4'-Pyrrolidinobutyl)-5-ethoxyoxazole
• 英文别名: 5-Ethoxy-2-(4-pyrrolidin-1-ylbutyl)-1,3-oxazole
• CAS: 140662-72-2
• 化学式: C₁₃H₂₂N₂O₂
• 分子量: 238.33
• InChiKey: QVPKTPXJHQAIOX-UHFFFAOYSA-N

物化性质

• 沸点：
  338.2±22.0 °C(Predicted)
• 密度：
  1.047±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  38.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-溴戊腈 在 三氟化硼乙醚 、 sodium iodide 作用下， 以 乙腈 为溶剂， 反应 13.5h， 生成 2-(4'-Pyrrolidinobutyl)-5-ethoxyoxazole
  参考文献：
  名称：

  Cycloadditions. 50. Multipath reactions between intramolecularly formed oxazolium salts and nucleophiles

  摘要：

  Reaction of 2-(4'-bromobutyl)-5-ethoxyoxazole (1) with nucleophiles led either to S(N)2 substitution products or to products with a piperidine skeleton. The latter were shown to arise from an intramolecular ring closure to an oxazolium salt 7, which was faster in the presence of a catalytic amount of NaI and in a polar solvent and for which NMR evidence is presented. The further transformation of 7 to 3-6 apparently involves addition of nucleophiles to 7 to produce 4-oxazoline 8 which opens to azomethine ylide 9. Neutralization of the latter occurred either via a proton shift, an alkyl shift, or via trapping by a dipolarophile (electron poor or electron rich). FMO calculations explain the preferred regiochemistry observed during trapping of ylide 9b.

  DOI：

  10.1021/jo00037a023