3-methoxy-8-trifluoromethanesulfonyl-6,7,8,9,10,10a-hexahydro-1H-2-oxa-8-aza-cycloocta[cd]indene | 372516-23-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 3-methoxy-8-trifluoromethanesulfonyl-6,7,8,9,10,10a-hexahydro-1H-2-oxa-8-aza-cycloocta[cd]indene
• CAS: 372516-23-9
• 化学式: C₁₄H₁₆F₃NO₄S
• 分子量: 351.347
• InChiKey: NDMKOKVEYWUFKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.27
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  55.84
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  3-methoxy-8-trifluoromethanesulfonyl-6,7,8,9,10,10a-hexahydro-1H-2-oxa-8-aza-cycloocta[cd]indene 在 lithium aluminium tetrahydride 、 三溴化硼 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 36.0h， 生成 8-methyl-6,7,8,9,10,10a-hexahydro-1H-2-oxa-8-aza-cycloocta[cd]inden-3-ol
  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：

  在 Wilkinson's catalyst 、 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 24.0h， 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