5-Ethoxy-3-ethyl-2-phenyl-oxazolium tetrafluoroborate | 140662-75-5

• 英文名称: 5-Ethoxy-3-ethyl-2-phenyl-oxazolium tetrafluoroborate
• CAS: 140662-75-5
• 化学式: BF₄*C₁₃H₁₈NO₂
• 分子量: 307.096
• InChiKey: LCJYRNGSQIUCRF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
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• 重原子数：
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• 可旋转键数：
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• 环数：
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• sp3杂化的碳原子比例：
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• 拓扑面积：
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• 氢给体数：
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• 氢受体数：
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反应信息

• 作为反应物：
  描述：

  5-Ethoxy-3-ethyl-2-phenyl-oxazolium tetrafluoroborate 在 氰化钠 作用下， 以 丙酮 为溶剂， 反应 24.0h， 以62%的产率得到马尿酸乙酯
  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