N-phenyl-3-phenyl-4-vinyl-1,3-oxazin-2-imine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-phenyl-3-phenyl-4-vinyl-1,3-oxazin-2-imine
• 英文别名: 4-ethenyl-N,3-diphenyl-1,3-oxazinan-2-imine
• 化学式: C₁₈H₁₈N₂O
• 分子量: 278.354
• InChiKey: VAHMQXXYMVIHOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  24.8
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3,5-epoxy-1-pentene 、 2-氯-5-异氰酸硝基苯 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 1,3-双(二苯基膦)丙烷 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以98%的产率得到N-phenyl-3-phenyl-4-vinyl-1,3-oxazin-2-imine
  参考文献：
  名称：

  Synthesis of 1,3-Oxazine Derivatives by Palladium-Catalyzed Cycloaddition of Vinyloxetanes with Heterocumulenes. Completely Stereoselective Synthesis of Bicyclic 1,3-Oxazines

  摘要：

  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.

  DOI：

  10.1021/jo990430b

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.