N-phenyl-4-vinyl-1,3-oxazin-2-one | 145198-87-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑烷类
• 英文名称: N-phenyl-4-vinyl-1,3-oxazin-2-one
• 英文别名: 4-Ethenyl-3-phenyl-1,3-oxazinan-2-one
• CAS: 145198-87-4
• 化学式: C₁₂H₁₃NO₂
• 分子量: 203.241
• InChiKey: PTIXYYJLSMCOSC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  29.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-vinyl-1,3-dioxan-2-one 、 异氰酸苯酯 在 四(三苯基膦)钯 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以70%的产率得到N-phenyl-4-vinyl-1,3-oxazin-2-one
  参考文献：
  名称：

  Palladium-catalysed regio- and stereo-selective synthesis of allylic amines

  摘要：

  3-乙烯基-2,6-二氧杂环己烷-1-酮 1 经 N-对甲基苯磺酰或 N-芳基异氰酸酯和催化量的 Pd0 处理后，以良好的收率和独特的立体选择性转化为 N-对甲基苯磺酰和 N-芳基-3-乙烯基-2-氮杂-6-氧杂环己烷-1-酮 2。

  DOI：

  10.1039/c39920001498

文献信息

• Synthesis of 1,3-Oxazine Derivatives by Palladium-Catalyzed Cycloaddition of Vinyloxetanes with Heterocumulenes. Completely Stereoselective Synthesis of Bicyclic 1,3-Oxazines
  作者：Chitchamai Larksarp、Howard Alper

  DOI：10.1021/jo990430b

  日期：1999.5.1

  1,3-Oxazines were prepared by palladium-phosphine-catalyzed cycloaddition reactions of vinyloxetanes with heterocumulenes. 4-Vinyl-1,3-oxazin-2-imines were obtained in fine yields by the reaction of 2-vinyloxetanes with carbodiimides in THF at rt for 12 h using 1.5 mol % Pd-2(dba)(3). CHCl3 and 3 mol % bidentate phosphine ligands (dppe or dppp). When isocyanates were utilized in the reaction, moderate to good yields of 4-vinyl-1,3-oxazin-2-ones were achieved within 1-2 h at rt. Palladium-catalyzed cycloaddition of fused-bicyclic vinyloxetanes with heterocumulenes proceeds in a highly stereoselective fashion affording only the cis-3-aza-1-oxo-9-vinyl[4.4.0]decane derivatives in 43-98% yield.