3-benzyl-1-hydroxy-7,8-dimethoxy-1,3,4,5-tetrahydro-benzo[d]azepin-2-one | 596093-62-8

• 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-1-hydroxy-7,8-dimethoxy-1,3,4,5-tetrahydro-benzo[d]azepin-2-one
• 英文别名: 3-benzyl-4,5-dihydro-1-hydroxy-7,8-dimethoxy-1H-benzo[d]azepin-2(3H)-one；3-benzyl-5-hydroxy-7,8-dimethoxy-2,5-dihydro-1H-3-benzazepin-4-one
• CAS: 596093-62-8
• 化学式: C₁₉H₂₁NO₄
• 分子量: 327.38
• InChiKey: XIWCTIWEJANMKH-UHFFFAOYSA-N

物化性质

• 熔点：
  131-132 °C(Solv: ethyl acetate (141-78-6); hexane (110-54-3))
• 沸点：
  557.4±50.0 °C(Predicted)
• 密度：
  1.236±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  59
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-benzyl-1-hydroxy-7,8-dimethoxy-1,3,4,5-tetrahydro-benzo[d]azepin-2-one 在 三甲基氯硅烷 、 potassium tert-butylate 、 氨 、 sodium 、 sodium iodide 作用下， 以 四氢呋喃 、 二甲基亚砜 、 乙腈 为溶剂， 反应 26.5h， 生成 扎替雷定
  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
• 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 21.0h， 生成 3-benzyl-1-hydroxy-7,8-dimethoxy-1,3,4,5-tetrahydro-benzo[d]azepin-2-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.
• Tetrahedron Lett. 2003, 44, 4203-4206
  作者：

  DOI：——

  日期：——
• 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
  作者：Mickaël Pauvert、Sylvain Collet、André Guingant

  DOI：10.1016/s0040-4039(03)00919-5

  日期：2003.5

  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.