2,3,10,11-tetramethoxy-14,14a-dihydro-13H-isoquino[2,1-b][2]benzazepin-8-one | 1383563-85-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 2,3,10,11-tetramethoxy-14,14a-dihydro-13H-isoquino[2,1-b][2]benzazepin-8-one
• 英文别名: 5,6,14,15-Tetramethoxy-1-azatetracyclo[9.8.0.03,8.012,17]nonadeca-3,5,7,12,14,16,18-heptaen-2-one
• CAS: 1383563-85-6
• 化学式: C₂₂H₂₃NO₅
• 分子量: 381.428
• InChiKey: TXCPZGSATSWJEH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,3,10,11-tetramethoxy-14,14a-dihydro-13H-isoquino[2,1-b][2]benzazepin-8-one 在 palladium 10% on activated carbon 、 甲酸铵 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以88%的产率得到2,3,10,11-tetramethoxy-5,6,14,14a-tetrahydrobenzo[5,6]azepino[2,1-a]isoquinolin-8(13H)-one
  参考文献：
  名称：

  A Concise Synthesis of 3-Arylated Di- and Tetrahydro-2H-2-benzazepin-1-ones; A New Synthetic Approach to the Homoprotoberberine Framework

  摘要：

  A variety of 3-arylated di- and tetrahydro-2H-2-benzazepin-1-ones were efficiently assembled through a sequence involving a Suzuki-Miyaura cross-coupling reaction with enol phosphates derived from the corresponding benzazepine-1,3-diones. This technique has been further exploited for the construction of the homoprotoberberine skeleton, which was readily accessed by intramolecular carbocationic annulation reaction applied to a suitably substituted precursor.

  DOI：

  10.1055/s-0031-1290504
• 作为产物：
  描述：

  2-(2,2-dimethoxyethyl)-7,8-dimethoxy-1H-benzo[c]azepine-1,3(2H)-dione 在 四(三苯基膦)钯 、 硫酸 、 palladium 10% on activated carbon 、 氢气 、 双(三甲基硅烷基)氨基钾 、 sodium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 、 水 、 甲苯 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 27.0h， 生成 2,3,10,11-tetramethoxy-14,14a-dihydro-13H-isoquino[2,1-b][2]benzazepin-8-one
  参考文献：
  名称：

  A Concise Synthesis of 3-Arylated Di- and Tetrahydro-2H-2-benzazepin-1-ones; A New Synthetic Approach to the Homoprotoberberine Framework

  摘要：

  A variety of 3-arylated di- and tetrahydro-2H-2-benzazepin-1-ones were efficiently assembled through a sequence involving a Suzuki-Miyaura cross-coupling reaction with enol phosphates derived from the corresponding benzazepine-1,3-diones. This technique has been further exploited for the construction of the homoprotoberberine skeleton, which was readily accessed by intramolecular carbocationic annulation reaction applied to a suitably substituted precursor.

  DOI：

  10.1055/s-0031-1290504

文献信息

• A Concise Synthesis of 3-Arylated Di- and Tetrahydro-2H-2-benzazepin-1-ones; A New Synthetic Approach to the Homoprotoberberine Framework
  作者：Axel Couture、Stéphane Lebrun、Eric Deniau、Pierre Grandclaudon

  DOI：10.1055/s-0031-1290504

  日期：2012.5

  A variety of 3-arylated di- and tetrahydro-2H-2-benzazepin-1-ones were efficiently assembled through a sequence involving a Suzuki-Miyaura cross-coupling reaction with enol phosphates derived from the corresponding benzazepine-1,3-diones. This technique has been further exploited for the construction of the homoprotoberberine skeleton, which was readily accessed by intramolecular carbocationic annulation reaction applied to a suitably substituted precursor.