4-methyl-2-oxido-4H-chromeno[4,3-d]oxazin-2-ium-5-one | 949449-14-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4-methyl-2-oxido-4H-chromeno[4,3-d]oxazin-2-ium-5-one
• CAS: 949449-14-3
• 化学式: C₁₂H₉NO₄
• 分子量: 231.208
• InChiKey: RNNMOHXSCRSSMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methyl-2-oxido-4H-chromeno[4,3-d]oxazin-2-ium-5-one 、 (E)-1-ethoxyprop-1-ene 以 甲苯 为溶剂， 反应 26.0h， 以86%的产率得到(11S,15S,16S,17S)-15-ethoxy-11,16-dimethyl-8,12,14-trioxa-13-azatetracyclo[8.7.0.02,7.013,17]heptadeca-1(10),2,4,6-tetraen-9-one
  参考文献：
  名称：

  Phosphine-Catalyzed Synthesis of Highly Functionalized Coumarins

  摘要：

  [GRAPHICS]2-Styrenyl allenoates are converted into cyclopentene-fused dihydrocoumarins through phosphine-catalyzed regio- and diastereoselective [3 + 2] cycloadditions. Remarkably, changing the solvent from THF to benzene promotes the conversion of the 2-(2-nitrostyrenyl) allenoate into a tricyclic nitronate through a previously undocumented mode of phosphine catalysis. This nitronate was subjected to efficient face-, regio-, and exo-selective 1,3-dipolar cycloadditions to provide tetracyclic coumarin derivatives.

  DOI：

  10.1021/ol071181d
• 作为产物：
  描述：

  反-2-羟基-β-硝基苯乙烯 在 potassium carbonate 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 5.0h， 生成 4-methyl-2-oxido-4H-chromeno[4,3-d]oxazin-2-ium-5-one
  参考文献：
  名称：

  Phosphine-Catalyzed Synthesis of Highly Functionalized Coumarins

  摘要：

  [GRAPHICS]2-Styrenyl allenoates are converted into cyclopentene-fused dihydrocoumarins through phosphine-catalyzed regio- and diastereoselective [3 + 2] cycloadditions. Remarkably, changing the solvent from THF to benzene promotes the conversion of the 2-(2-nitrostyrenyl) allenoate into a tricyclic nitronate through a previously undocumented mode of phosphine catalysis. This nitronate was subjected to efficient face-, regio-, and exo-selective 1,3-dipolar cycloadditions to provide tetracyclic coumarin derivatives.

  DOI：

  10.1021/ol071181d