2-(4'-Bromobutyl)-5-ethoxyoxazole | 132353-41-4

• 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'-Bromobutyl)-5-ethoxyoxazole
• 英文别名: 2-(4-bromobutyl)-5-ethoxyoxazole；Oxazole, 2-(4-bromobutyl)-5-ethoxy-；2-(4-bromobutyl)-5-ethoxy-1,3-oxazole
• CAS: 132353-41-4
• 化学式: C₉H₁₄BrNO₂
• 分子量: 248.12
• InChiKey: DLHRTZUGDSLJEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4'-Bromobutyl)-5-ethoxyoxazole 在 sodium iodide 三氟化硼乙醚 、 potassium thioacyanate 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 9.5h， 生成 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：

  重氮乙酸乙酯 、 5-溴戊腈 在 三氟化硼乙醚 作用下， 生成 2-(4'-Bromobutyl)-5-ethoxyoxazole
  参考文献：
  名称：

  Fischer, Bilha; Hassner, Alfred; Wolk, Joel L., Acta Chemica Scandinavica, 1993, vol. 47, # 2, p. 191 - 195

  摘要：

  DOI：

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.
• Intramolecular formation of oxazolium salts and their reaction with N- and C-nucleophiles.
  作者：Alfred Hassner、Bilha Fischer

  DOI：10.1016/s0040-4039(00)97282-4

  日期：1990.1
• HASSNER, ALFRED;FISCHER, BILHA, TETRAHEDRON LETT., 31,(1990) N9, C. 7213-7214
  作者：HASSNER, ALFRED、FISCHER, BILHA

  DOI：——

  日期：——