2-(7-Methoxy-2,3-dihydro-1-benzofuran-3-yl)ethanamine | 372516-20-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 英文名称: 2-(7-Methoxy-2,3-dihydro-1-benzofuran-3-yl)ethanamine
• 英文别名: 2-(7-methoxy-2,3-dihydro-1-benzofuran-3-yl)ethanamine
• CAS: 372516-20-6
• 化学式: C₁₁H₁₅NO₂
• 分子量: 193.246
• InChiKey: SVNKFDOLBLLOJJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  44.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(7-Methoxy-2,3-dihydro-1-benzofuran-3-yl)ethanamine 在 Wilkinson's catalyst 、 4 A molecular sieve 、 四氯化锡 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 氯仿 、 甲苯 为溶剂， 反应 26.0h， 生成 3-methoxy-8-trifluoromethanesulfonyl-6,7,8,9,10,10a-hexahydro-1H-2-oxa-8-aza-cycloocta[cd]indene
  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-溴-6-甲氧基苯酚 在 偶氮二异丁腈 、 dimethyl sulfide borane 、 三正丁基氢锡 、 caesium carbonate 作用下， 以 四氢呋喃 、 丙酮 、 苯 为溶剂， 反应 17.25h， 生成 2-(7-Methoxy-2,3-dihydro-1-benzofuran-3-yl)ethanamine
  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.