2-(4'-(Phenylthio)butyl)-5-ethoxyoxazole | 132353-43-6

• 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'-(Phenylthio)butyl)-5-ethoxyoxazole
• 英文别名: 5-Ethoxy-2-(4-phenylsulfanylbutyl)-1,3-oxazole
• CAS: 132353-43-6
• 化学式: C₁₅H₁₉NO₂S
• 分子量: 277.387
• InChiKey: JVQBJIXJNUBXBL-UHFFFAOYSA-N

物化性质

• 沸点：
  401.6±25.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  60.6
• 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 、 三乙胺 、 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 30.0h， 生成 2-(4'-(Phenylthio)butyl)-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

文献信息

• Cycloadditions. 50. Multipath reactions between intramolecularly formed oxazolium salts and nucleophiles
  作者：Alfred Hassner、Bilha Fischer

  DOI：10.1021/jo00037a023

  日期：1992.5

  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.

表征谱图