4-phenyl-3,4-dihydro-2H,5H-chromeno[3,4-e][1,3]oxazine-2,5-dione

• 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-phenyl-3,4-dihydro-2H,5H-chromeno[3,4-e][1,3]oxazine-2,5-dione
• 英文别名: 4-Phenyl-3,4-dihydro-2h,5h-chromeno[3,4-e]-[1,3]oxazine-2,5-dione；4-phenyl-3,4-dihydrochromeno[3,4-e][1,3]oxazine-2,5-dione
• 化学式: C₁₇H₁₁NO₄
• 分子量: 293.279
• InChiKey: ILTKFOOZGVQMRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-羟基香豆素 、 α-chlorobenzyl isocyanate 以 甲苯 为溶剂， 反应 4.0h， 以75%的产率得到4-phenyl-3,4-dihydro-2H,5H-chromeno[3,4-e][1,3]oxazine-2,5-dione
  参考文献：
  名称：

  Heterocyclization of functionalized heterocumulenes with C,N-, C,O-, and C,S-binucleophiles: VIII. Synthesis of pyrano(chromeno)[3,4-e][1,3]oxazines by condensation of 1-chloroalkyl isocyanates with 4-hydroxy-6-methylpyran-2-one and 4-hydroxycoumarin

  摘要：

  1-Chlorobenzyl isocyanates react with 4-hydroxy-6-methylpyran-2-one and 4-hydroxycoumarin forming 4-aryl-3,4-dihydro-2H,5H-pyrano(chromeno)[3,4-e][1,3]oxazine-2,5-diones. The reaction of 1-aryl-2,2,2-trifluoro-1-chloroethyl isocyanates with the above substrates gives rise to structurally isomeric 2-aryl-2-trifluoromethyl-2,3-dihydro-2H,5H-pyrano(chromeno)[3,4-e][1,3]-oxazine-4,5-diones.

  DOI：

  10.1134/s1070428007080179

文献信息

• Green Synthesis of 4-aryl-3,4-Dihydrochromeno[3,4-e][1,3]Oxazine-2,5-Dione in Aqueous Media by Condensation of 4-Hydroxycoumarin with Aromatic Aldehydes and Methyl Carbamate
  作者：Sabereh Bougan、Alireza Hassanabadi

  DOI：10.3184/174751917x14859570937758

  日期：2017.3

  A green and efficient synthesis of the title compounds has been achieved in a one-pot, three-component reaction of 4-hydroxycoumarin and aromatic aldehydes with methyl carbamate catalysed by p-toluenesulfonic acid in aqueous media to afford 4-aryl-3,4-dihydrochromeno[3,4-e][1,3]oxazine-2,5-diones in excellent yields. The salient features of this protocol are: short reaction times, high yields and absence

  在对甲苯磺酸的催化下，4-羟基香豆素和芳香醛与氨基甲酸甲酯在水性介质中的一锅三组分反应中实现了标题化合物的绿色高效合成，得到4-芳基-3,4 -dihydrochromeno[3,4-e][1,3]oxazine-2,5-diones，产率极好。该协议的显着特点是：反应时间短、收率高且不含任何有害有机溶剂。因此，该过程可归类为绿色化学。
• Heterocyclization of functionalized heterocumulenes with C,N-, C,O-, and C,S-binucleophiles: VIII. Synthesis of pyrano(chromeno)[3,4-e][1,3]oxazines by condensation of 1-chloroalkyl isocyanates with 4-hydroxy-6-methylpyran-2-one and 4-hydroxycoumarin
  作者：M. V. Vovk、V. A. Sukach、V. I. Dorokhov

  DOI：10.1134/s1070428007080179

  日期：2007.8

  1-Chlorobenzyl isocyanates react with 4-hydroxy-6-methylpyran-2-one and 4-hydroxycoumarin forming 4-aryl-3,4-dihydro-2H,5H-pyrano(chromeno)[3,4-e][1,3]oxazine-2,5-diones. The reaction of 1-aryl-2,2,2-trifluoro-1-chloroethyl isocyanates with the above substrates gives rise to structurally isomeric 2-aryl-2-trifluoromethyl-2,3-dihydro-2H,5H-pyrano(chromeno)[3,4-e][1,3]-oxazine-4,5-diones.