2-(5',5'Dicarbomethoxypentyl)-5-ethoxyoxazole | 140662-71-1

• 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-(5',5'Dicarbomethoxypentyl)-5-ethoxyoxazole
• 英文别名: Dimethyl 2-[4-(5-ethoxy-1,3-oxazol-2-yl)butyl]propanedioate
• CAS: 140662-71-1
• 化学式: C₁₄H₂₁NO₆
• 分子量: 299.324
• InChiKey: QHDUYQCOCFGZQL-UHFFFAOYSA-N

物化性质

• 沸点：
  373.0±37.0 °C(Predicted)
• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  87.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5-溴戊腈 在 三氟化硼乙醚 、 sodium hydride 、 sodium iodide 作用下， 反应 32.17h， 生成 2-(5',5'Dicarbomethoxypentyl)-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