N-(2,2-dimethyl-4H-[1,3]dioxin-5-yl)-trifluoro-N-[2-(3-methoxyphenyl)-ethyl]-methanesulfonamide | 372516-02-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: N-(2,2-dimethyl-4H-[1,3]dioxin-5-yl)-trifluoro-N-[2-(3-methoxyphenyl)-ethyl]-methanesulfonamide
• 英文别名: N-(2,2-dimethyl-4H-1,3-dioxin-5-yl)-1,1,1-trifluoro-N-[2-(3-methoxyphenyl)ethyl]methanesulfonamide
• CAS: 372516-02-4
• 化学式: C₁₆H₂₀F₃NO₅S
• 分子量: 395.4
• InChiKey: XWCAOCXZRIETHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  73.4
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-(2,2-dimethyl-4H-[1,3]dioxin-5-yl)-trifluoro-N-[2-(3-methoxyphenyl)-ethyl]-methanesulfonamide 在 四氯化锡 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 0.75h， 以68%的产率得到7-methoxy-3-trifluoromethanesulfonyl-2,3,4,5-tetrahydro-1H-benzo[d]azepine-2-carbaldehyde
  参考文献：
  名称：

  Intramolecular Electrophilic Aromatic Substitution Reactions of 2-Amidoacroleins:  A New Method for the Preparation of Tetrahydroisoquinolines, Tetrahydro-3-benzazepines, and Hexahydro-3-benzazocines

  摘要：

  [GRAPHICS]A variety of heterocyclic ring systems can be prepared by subjecting N-aryl-substituted 5-amido-1,3-dioxins to Lewis acids. The reactions proceed via catalyzed retrocycloadditions to afford 2-amidoacroleins and concomitant regioselective electrophilic aromatic substitution reactions. The transformation is also successful using dioxins with amides that are within the incipient ring to afford the analogous lactams.

  DOI：

  10.1021/ol016592n
• 作为产物：
  描述：

  2,2-二甲基-1,3-二恶烷-5-酮 在 palladium dihydroxide 4 A molecular sieve 、 氢气 、 caesium carbonate 、 三乙胺 作用下， 以 甲醇 、 丙酮 、 甲苯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 63.25h， 生成 N-(2,2-dimethyl-4H-[1,3]dioxin-5-yl)-trifluoro-N-[2-(3-methoxyphenyl)-ethyl]-methanesulfonamide
  参考文献：
  名称：

  Intramolecular Electrophilic Aromatic Substitution Reactions of 2-Amidoacroleins:  A New Method for the Preparation of Tetrahydroisoquinolines, Tetrahydro-3-benzazepines, and Hexahydro-3-benzazocines

  摘要：

  [GRAPHICS]A variety of heterocyclic ring systems can be prepared by subjecting N-aryl-substituted 5-amido-1,3-dioxins to Lewis acids. The reactions proceed via catalyzed retrocycloadditions to afford 2-amidoacroleins and concomitant regioselective electrophilic aromatic substitution reactions. The transformation is also successful using dioxins with amides that are within the incipient ring to afford the analogous lactams.

  DOI：

  10.1021/ol016592n

文献信息

• Intramolecular Electrophilic Aromatic Substitution Reactions of 2-Amidoacroleins:  A New Method for the Preparation of Tetrahydroisoquinolines, Tetrahydro-3-benzazepines, and Hexahydro-3-benzazocines
  作者：James R. Fuchs、Raymond L. Funk

  DOI：10.1021/ol016592n

  日期：2001.10.1

  [GRAPHICS]A variety of heterocyclic ring systems can be prepared by subjecting N-aryl-substituted 5-amido-1,3-dioxins to Lewis acids. The reactions proceed via catalyzed retrocycloadditions to afford 2-amidoacroleins and concomitant regioselective electrophilic aromatic substitution reactions. The transformation is also successful using dioxins with amides that are within the incipient ring to afford the analogous lactams.