2,3,10,11-tetramethoxy-5,6,14,14a-tetrahydrobenzo[5,6]azepino[2,1-a]isoquinolin-8(13H)-one | 1383563-86-7

• 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-5,6,14,14a-tetrahydrobenzo[5,6]azepino[2,1-a]isoquinolin-8(13H)-one
• 英文别名: 2,3,10,11-tetramethoxy-5,13,14,14a-tetrahydro-6H-isoquino[2,1-b][2]benzazepin-8-one；5,6,14,15-Tetramethoxy-1-azatetracyclo[9.8.0.03,8.012,17]nonadeca-3,5,7,12,14,16-hexaen-2-one
• CAS: 1383563-86-7
• 化学式: C₂₂H₂₅NO₅
• 分子量: 383.444
• InChiKey: WQSIVTIBXWFZGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  57.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-(2,2-dimethoxyethyl)-4,5-dimethoxy-2-vinylbenzamide 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 四(三苯基膦)钯 、 硫酸 、 palladium 10% on activated carbon 、 氢气 、 甲酸铵 、 双(三甲基硅烷基)氨基钾 、 sodium hydride 、 sodium carbonate 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 水 、 甲苯 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 40.5h， 生成 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

文献信息

• Mild Rhodium(III)-Catalyzed Cyclization of Amides with α,β-Unsaturated Aldehydes and Ketones to Azepinones: Application to the Synthesis of the Homoprotoberberine Framework
  作者：Zhuangzhi Shi、Christoph Grohmann、Frank Glorius

  DOI：10.1002/anie.201301426

  日期：2013.5.10

  Seven! The title reaction can be described as an intermolecular annulation involving tandem CH activation, cyclization to give the seven‐membered ring, and condensation steps. Biologically interesting azepinone derivatives can be prepared in this way. The synthetic potential of this method was demonstrated by the construction of the homoprotoberberine ring system.

  七！标题反应可以描述为分子间的环化反应，涉及串联CH活化，环化生成七元环以及缩合步骤。可以通过这种方式制备生物学上令人感兴趣的氮杂环庚酮衍生物。该方法的合成潜力由高原小ber碱环系统的构建证明。
• 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.