2-Benzyl-4,5-dihydro-2-benzazepine-1,3-dione | 137643-61-9

• 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-Benzyl-4,5-dihydro-2-benzazepine-1,3-dione
• 英文别名: 2-benzyl-4,5-dihydro-2-benzazepine-1,3-dione
• CAS: 137643-61-9
• 化学式: C₁₇H₁₅NO₂
• 分子量: 265.312
• InChiKey: VKUDOHSKDQNOAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-Benzyl-4,5-dihydro-2-benzazepine-1,3-dione 在 四(三苯基膦)钯 、 palladium 10% on activated carbon 、 氢气 、 双(三甲基硅烷基)氨基钾 、 sodium carbonate 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 14.5h， 生成 2-benzyl-3-phenyl-4,5-dihydro-3H-2-benzazepin-1-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：

  N-benzyl-2-ethenyl-N-prop-2-enoylbenzamide 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 、 甲苯 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 17.0h， 生成 2-Benzyl-4,5-dihydro-2-benzazepine-1,3-dione
  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.