6-Chloro-N-(4-methylphenylsulfonyl)-4-phenyl-1,4-dihydro-2H-3,1-benzoxazin-2-one | 182145-46-6

• 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: 6-Chloro-N-(4-methylphenylsulfonyl)-4-phenyl-1,4-dihydro-2H-3,1-benzoxazin-2-one
• 英文别名: 6-chloro-1-(4-methylphenyl)sulfonyl-4-phenyl-4H-3,1-benzoxazin-2-one
• CAS: 182145-46-6
• 化学式: C₂₁H₁₆ClNO₄S
• 分子量: 413.881
• InChiKey: IIYPMKGRSDIKIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 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：

  6-Chloro-N-(4-methylphenylsulfonyl)-4-phenyl-1,4-dihydro-2H-3,1-benzoxazin-2-one 在 N-苯基马来酰亚胺 作用下， 以 various solvent(s) 为溶剂， 反应 5.0h， 以16%的产率得到
  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：

  (2-amino-5-chlorophenyl)(phenyl)methanol 在 吡啶 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 氯仿 为溶剂， 生成 6-Chloro-N-(4-methylphenylsulfonyl)-4-phenyl-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

文献信息

• 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.