N-(4-甲基苯基磺酰基)-1,4-二氢-2H-3,1-苯并噁嗪-2-酮 | 182145-44-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 中文名称: N-(4-甲基苯基磺酰基)-1,4-二氢-2H-3,1-苯并噁嗪-2-酮
• 英文名称: N-(4-Methylphenylsulfonyl)-1,4-dihydro-2H-3,1-benzoxazin-2-one
• 英文别名: 1-Tosyl-4H-3,1-benzoxazine-2(1H)-one；1-(4-methylphenyl)sulfonyl-4H-3,1-benzoxazin-2-one
• CAS: 182145-44-4
• 化学式: C₁₅H₁₃NO₄S
• 分子量: 303.339
• InChiKey: JXVKKFZWABUXGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 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：

  (E)-1-phenyl-3-(phenylsulfonyl)prop-2-en-1-one 、 N-(4-甲基苯基磺酰基)-1,4-二氢-2H-3,1-苯并噁嗪-2-酮 以 various solvent(s) 为溶剂， 以30%的产率得到苯基-喹啉-3-基甲酮
  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， 生成 N-(4-甲基苯基磺酰基)-1,4-二氢-2H-3,1-苯并噁嗪-2-酮
  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.