N-Pent-4-enyl-sulfonyl-1,4-dihydro-2H-3,1-benzoxazin-2-one | 182145-52-4

• 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: N-Pent-4-enyl-sulfonyl-1,4-dihydro-2H-3,1-benzoxazin-2-one
• 英文别名: 1-pent-4-enylsulfonyl-4H-3,1-benzoxazin-2-one
• CAS: 182145-52-4
• 化学式: C₁₃H₁₅NO₄S
• 分子量: 281.332
• InChiKey: ZJGRPGDXLPCEQP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-Pent-4-enyl-sulfonyl-1,4-dihydro-2H-3,1-benzoxazin-2-one 以 various solvent(s) 为溶剂， 反应 2.0h， 以34%的产率得到2,3,4,4a,5,6-Hexahydrothiazino[2,3-a]quinoline 1,1-dioxide
  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
• 作为产物：
  描述：

  邻氨基苯甲醇 在 吡啶 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 氯仿 为溶剂， 反应 1.0h， 生成 N-Pent-4-enyl-sulfonyl-1,4-dihydro-2H-3,1-benzoxazin-2-one
  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