3-benzyl-4,5-dihydro-1,7,8-trimethoxy-1H-benzo[d]azepin-2(3H)-one

• 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: 3-benzyl-4,5-dihydro-1,7,8-trimethoxy-1H-benzo[d]azepin-2(3H)-one
• 英文别名: 3-benzyl-5,7,8-trimethoxy-2,5-dihydro-1H-3-benzazepin-4-one
• 化学式: C₂₀H₂₃NO₄
• 分子量: 341.407
• InChiKey: CUVJPHQEIIOSCE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  6,7-二甲氧基-3,4-二氢异喹啉 在 氢氧化钾 、 silver nitrate 作用下， 以 水 、 甲苯 、 乙腈 为溶剂， 反应 5.0h， 生成 3-benzyl-4,5-dihydro-1,7,8-trimethoxy-1H-benzo[d]azepin-2(3H)-one
  参考文献：
  名称：

  Silver nitrate-promoted ring enlargement of 1-tribromomethyl-1,2-dihydro- and 1-tribromomethyl-1,2,3,4-tetrahydro-isoquinoline derivatives: application to the synthesis of the anti-anginal zatebradine

  摘要：

  The one step AgNO3-mediated ring enlargement of 1-tribromomethyl-1,2-dihydro- and 1-tribromomethyl-1,2,3,4-tetrahydro-isoquinoline derivatives into 1,2-dihydro- and 1,2,3,4-tetrahydro-benzo[d]azepin-2-ones, respectively, is reported. This reaction offers a convenient entry to potentially active substances such as the anti-anginal zatebradine. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00919-5

文献信息

• A new enlargement methodology for the preparation of 2H-1- and 2H-3-benzazepin-2-one derivatives
  作者：Ludivine Jean-Gérard、Mickaël Pauvert、Sylvain Collet、André Guingant、Michel Evain

  DOI：10.1016/j.tet.2007.08.094

  日期：2007.11

  An investigation of the one-carbon homologation of some 1-tribromomethyl-isoquinoline and 2-tribromomethyl-quinoline derivatives was conducted. Under the influence of an aqueous solution of silver nitrate in the presence of a nucleophilic species (MeOH, H2O, EtNH2), these derivatives led to the respective expanded heterocycles, 2H-1- and 2H-3-benzazepin-2-one derivatives. A mechanism for this novel ring enlargement involving initial formation of an aziridinium, and its subsequent opening to form a stabilized benzylic carbocation, is proposed to explain the results. (C) 2007 Elsevier Ltd. All rights reserved.