4-butyl-3-methyl-1,3,4,5-tetrahydro-3-benzazepin-2-one | 1365254-30-3

• 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: 4-butyl-3-methyl-1,3,4,5-tetrahydro-3-benzazepin-2-one
• 英文别名: 2-butyl-3-methyl-2,5-dihydro-1H-3-benzazepin-4-one
• CAS: 1365254-30-3
• 化学式: C₁₅H₂₁NO
• 分子量: 231.338
• InChiKey: GSUHSSCVEIHMDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  2-[2-(2-oxohexyl)phenyl]acetic acid 在 palladium on activated charcoal 、 ammonium acetate 、 氢气 、 四丁基碘化铵 、 potassium hydroxide 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 20.0~120.0 ℃ 、500.01 kPa 条件下， 反应 4.0h， 生成 4-butyl-3-methyl-1,3,4,5-tetrahydro-3-benzazepin-2-one
  参考文献：
  名称：

  Microwave assisted synthesis of 3-benzazepin-2-ones as building blocks for 2,3-disubstituted tetrahydro-3-benzazepines

  摘要：

  Microwave assisted condensation of primary amines with keto acids 1a-c provided directly 3,4-disubstituted 1,3-dihydro-3-benzazepin-2-ones 2. Whereas small amine size, such as NH3 afforded high yields of secondary lactams 2a, 2d, and 2g, primary amines with larger substituents in alpha-position led to lower yields of 2 or even to regioisomeric indanone derivatives 4. However, subsequent alkylation of 2a, 2d, and 2g with various alkyl halides provided the corresponding N-substituted 3-benzazepin-2-ones 2 in good yields. Hydrogenation of 2 followed by BH3 reduction led to 3-benzazepines 9. 3-Benzyl-2-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (9c) reveals high sigma(1) affinity and selectivity over sigma(2) and NMDA receptors. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.01.052

文献信息

• Microwave assisted synthesis of 3-benzazepin-2-ones as building blocks for 2,3-disubstituted tetrahydro-3-benzazepines
  作者：Soumya Sarkar、Syed Masood Husain、Dirk Schepmann、Roland Fröhlich、Bernhard Wünsch

  DOI：10.1016/j.tet.2012.01.052

  日期：2012.3

  Microwave assisted condensation of primary amines with keto acids 1a-c provided directly 3,4-disubstituted 1,3-dihydro-3-benzazepin-2-ones 2. Whereas small amine size, such as NH3 afforded high yields of secondary lactams 2a, 2d, and 2g, primary amines with larger substituents in alpha-position led to lower yields of 2 or even to regioisomeric indanone derivatives 4. However, subsequent alkylation of 2a, 2d, and 2g with various alkyl halides provided the corresponding N-substituted 3-benzazepin-2-ones 2 in good yields. Hydrogenation of 2 followed by BH3 reduction led to 3-benzazepines 9. 3-Benzyl-2-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (9c) reveals high sigma(1) affinity and selectivity over sigma(2) and NMDA receptors. (C) 2012 Elsevier Ltd. All rights reserved.