2-(4'-Thiocyanatobutyl)-5-ethoxyoxazole | 133602-44-5

• 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'-Thiocyanatobutyl)-5-ethoxyoxazole
• 英文别名: 4-(5-Ethoxy-1,3-oxazol-2-yl)butyl thiocyanate
• CAS: 133602-44-5
• 化学式: C₁₀H₁₄N₂O₂S
• 分子量: 226.299
• InChiKey: ARPRTAWQKJCKNB-UHFFFAOYSA-N

物化性质

• 沸点：
  360.8±22.0 °C(Predicted)
• 密度：
  1.156±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  84.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(4'-Thiocyanatobutyl)-5-ethoxyoxazole 在 三氟化硼乙醚 作用下， 以 甲苯 为溶剂， 反应 7.0h， 以48%的产率得到Ethyl N-(5-thiocyanatopentanoyl)glycinate
  参考文献：
  名称：

  Cycloadditions. 48. Novel heterocycles by bis heteroannulation of oxazoles

  摘要：

  We report the first examples of intramolecular Diels-Alder addition of heterodienophiles N = N, C =N, C = O, C = S to oxazoles. The required 5-ethoxy- and 5-phenyloxazoles were synthesized bearing a side chain of variable length on C-2 to which the different heterodienophiles are attached. The products of the thermal bis heteroannulation are 3-triazolines, imidazolines, oxazolines, or thiazolines fused to a five- to six-membered ring. Relative reactivities were established and the mechanism is discussed.

  DOI：

  10.1021/jo00010a044
• 作为产物：
  描述：

  2-(4'-Bromobutyl)-5-ethoxyoxazole 在 sodium iodide potassium thioacyanate 作用下， 以 丙酮 为溶剂， 反应 2.5h， 以88%的产率得到2-(4'-Thiocyanatobutyl)-5-ethoxyoxazole
  参考文献：
  名称：

  Cycloadditions. 48. Novel heterocycles by bis heteroannulation of oxazoles

  摘要：

  We report the first examples of intramolecular Diels-Alder addition of heterodienophiles N = N, C =N, C = O, C = S to oxazoles. The required 5-ethoxy- and 5-phenyloxazoles were synthesized bearing a side chain of variable length on C-2 to which the different heterodienophiles are attached. The products of the thermal bis heteroannulation are 3-triazolines, imidazolines, oxazolines, or thiazolines fused to a five- to six-membered ring. Relative reactivities were established and the mechanism is discussed.

  DOI：

  10.1021/jo00010a044

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.