ethyl 2-oxo-4H-3,1-benzoxazine-1-carboxylate | 182145-54-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: ethyl 2-oxo-4H-3,1-benzoxazine-1-carboxylate
• CAS: 182145-54-6
• 化学式: C₁₁H₁₁NO₄
• 分子量: 221.213
• InChiKey: ATYIHVMKYXYEHX-UHFFFAOYSA-N

物化性质

• 沸点：
  313.413±45.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.309±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  足球烯 、 ethyl 2-oxo-4H-3,1-benzoxazine-1-carboxylate 以 various solvent(s) 为溶剂， 反应 4.5h， 以46%的产率得到
  参考文献：
  名称：

  Synthesis of Fullerotetrahydroquinolines by Cycloaddition Reaction of C₆₀ with Aza-ortho-xylylenes

  摘要：

  本文报告了通过使用原位生成的氮杂邻二甲苯进行Diels-Alder反应，成功合成了富勒烯四氢喹啉。

  DOI：

  10.1055/s-1999-2587
• 作为产物：
  描述：

  1H-苯并[d][1,3]噁嗪-2(4h)-酮 、 氯甲酸乙酯 在 sodium hydride 作用下， 以 various solvent(s) 为溶剂， 以55%的产率得到ethyl 2-oxo-4H-3,1-benzoxazine-1-carboxylate
  参考文献：
  名称：

  Diels–Alder reactions of N-sulfonyl substituted aza-ortho-xylylenes generated from the corresponding 1,4-dihydro-2H-3,1-benzoxazin-2-one derivatives

  摘要：

  N-Tosyl- and N-alkylidene-sulfonyl substituted 1,4-dihydro-2N-3,1-benzoxazin-2-ones 2c-g easily undergo thermal carbon dioxide extrusion leading to the aza-ortho-xylylenes 3c-g, The intermediates 3c,d can be trapped by electron-poor ethylenic and acetylenic dienophiles, giving tetrahydroquinoline and quinoline derivatives, The reactions of 2c with non-symmetrical dienophiles are completely regioselective, N-Alkylidenesulfonyl substituted aza-ortho-xylylenes 3f-g undergo intramolecular Diels-Alder reactions leading to the tricyclic compounds 10 and 11, while the aza-ortho-xylylene generated from 4-(hex-5-enyl)-N-(4-methylphenylsulfonyl)-1,4-tetrahydro-2N-3,1-benzoxazin-2-one undergoes a [1,5] hydrogen shift leading to N-[2-(1E)-hepta-1,6-dien-1-ylphenyl]-4-methylbenzenesulfonamide.

  DOI：

  10.1039/p19960001809

文献信息

• Synthesis of Fullerotetrahydroquinolines by Cycloaddition Reaction of C₆₀ with Aza-<i>ortho</i>-xylylenes
  作者：Masatomi Ohno、Haruhiko Sato、Shoji Eguchi

  DOI：10.1055/s-1999-2587

  日期：1999.2

  This paper reports on the successful synthesis of fullerotetrahydroquinolines by using in situ generated aza-ortho-xylylenes using a Diels-Alder reaction.

  本文报告了通过使用原位生成的氮杂邻二甲苯进行Diels-Alder反应，成功合成了富勒烯四氢喹啉。
• Diels–Alder reactions of N-sulfonyl substituted aza-ortho-xylylenes generated from the corresponding 1,4-dihydro-2H-3,1-benzoxazin-2-one derivatives
  作者：Roberto Consonni、Piero Dalla Croce、Raffaella Ferraccioli、Concetta La Rosa

  DOI：10.1039/p19960001809

  日期：——

  N-Tosyl- and N-alkylidene-sulfonyl substituted 1,4-dihydro-2N-3,1-benzoxazin-2-ones 2c-g easily undergo thermal carbon dioxide extrusion leading to the aza-ortho-xylylenes 3c-g, The intermediates 3c,d can be trapped by electron-poor ethylenic and acetylenic dienophiles, giving tetrahydroquinoline and quinoline derivatives, The reactions of 2c with non-symmetrical dienophiles are completely regioselective, N-Alkylidenesulfonyl substituted aza-ortho-xylylenes 3f-g undergo intramolecular Diels-Alder reactions leading to the tricyclic compounds 10 and 11, while the aza-ortho-xylylene generated from 4-(hex-5-enyl)-N-(4-methylphenylsulfonyl)-1,4-tetrahydro-2N-3,1-benzoxazin-2-one undergoes a [1,5] hydrogen shift leading to N-[2-(1E)-hepta-1,6-dien-1-ylphenyl]-4-methylbenzenesulfonamide.