N'-Carbethoxy-2-(5'-phenyl-2'-oxazolyl)propanoic Hydrazide | 133602-41-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N'-Carbethoxy-2-(5'-phenyl-2'-oxazolyl)propanoic Hydrazide
• 英文别名: ethyl N-[3-(5-phenyl-1,3-oxazol-2-yl)propanoylamino]carbamate
• CAS: 133602-41-2
• 化学式: C₁₅H₁₇N₃O₄
• 分子量: 303.318
• InChiKey: AAIIDWOXSARLDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  93.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N'-Carbethoxy-2-(5'-phenyl-2'-oxazolyl)propanoic Hydrazide 在 碘苯二乙酸 作用下， 以 苯 为溶剂， 反应 2.0h， 以40%的产率得到2,3,5,6-Tetrahydro-5-oxo-2-benzoyl-3-carbethoxy-1,2,4-triazolo<2,3-a>pyrrole
  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：

  N-(3-Carbethoxypropanoyl)-ω-aminoacetophenone 在 碘代三甲硅烷 、 phosphorus pentoxide 、 N,N'-二环己基碳二亚胺 作用下， 以 氯仿 、 乙腈 为溶剂， 反应 26.0h， 生成 N'-Carbethoxy-2-(5'-phenyl-2'-oxazolyl)propanoic Hydrazide
  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. 48. Novel heterocycles by bis heteroannulation of oxazoles
  作者：A. Hassner、B. Fischer

  DOI：10.1021/jo00010a044

  日期：1991.5

  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.