N-(2,2-dimethyl-4H-[1,3]dioxin-5-yl)-N-phenethyl-acetamide | 372516-00-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(2,2-dimethyl-4H-[1,3]dioxin-5-yl)-N-phenethyl-acetamide
• 英文别名: N-(2,2-dimethyl-4H-1,3-dioxin-5-yl)-N-(2-phenylethyl)acetamide
• CAS: 372516-00-2
• 化学式: C₁₆H₂₁NO₃
• 分子量: 275.348
• InChiKey: QKPXVCWWDHTKAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2,2-dimethyl-4H-[1,3]dioxin-5-yl)-N-phenethyl-acetamide 在 三氯化铝 作用下， 以 硝基甲烷 为溶剂， 反应 12.0h， 以67%的产率得到3-acetyl-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 4 A molecular sieve 、 N,N-二异丙基乙胺 作用下， 以 甲苯 为溶剂， 反应 15.0h， 生成 N-(2,2-dimethyl-4H-[1,3]dioxin-5-yl)-N-phenethyl-acetamide
  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