1-thioacetyl-2,3,4,5-tetrahydro-1H-1-benzazepine | 604004-19-5

• 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: 1-thioacetyl-2,3,4,5-tetrahydro-1H-1-benzazepine
• 英文别名: 1-(2,3,4,5-Tetrahydro-1H-1-benzazepin-1-yl)ethane-1-thione；1-(2,3,4,5-tetrahydro-1-benzazepin-1-yl)ethanethione
• CAS: 604004-19-5
• 化学式: C₁₂H₁₅NS
• 分子量: 205.324
• InChiKey: YQQKLFVXJCJVDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-acetyl-2,3,4,5-tetrahydro-1H-1-benzazepine 在 劳森试剂 作用下， 以 六甲基磷酰三胺 为溶剂， 反应 2.5h， 以72%的产率得到1-thioacetyl-2,3,4,5-tetrahydro-1H-1-benzazepine
  参考文献：
  名称：

  Dynamic and Static Conformational Analysis of Acylated Tetrahydrobenzazepines

  摘要：

  A detailed high-field NMR analysis of several acylated tetrahydrobenzazepines, supported by molecular mechanics calculations, indicates that the heterocyclic ring in these compounds exists in a chair conformation, with the carbonyl oriented anti to the aryl moiety in the dominant rotamer. Surprisingly, ring methylenes are typically diastereotopic at room temperature, as the barriers for the process of enantiomerization of the seven-membered ring are much higher than expected. It is shown that ring inversion is correlated (but not concerted) with rotation of the amide moiety, as the carbonyl is forced out of conjugation with the nitrogen in the transition state.

  DOI：

  10.1021/jo0340105

文献信息

• Dynamic and Static Conformational Analysis of Acylated Tetrahydrobenzazepines
  作者：Alfred Hassner、Boaz Amit、Vered Marks、Hugo E. Gottlieb

  DOI：10.1021/jo0340105

  日期：2003.9.1

  A detailed high-field NMR analysis of several acylated tetrahydrobenzazepines, supported by molecular mechanics calculations, indicates that the heterocyclic ring in these compounds exists in a chair conformation, with the carbonyl oriented anti to the aryl moiety in the dominant rotamer. Surprisingly, ring methylenes are typically diastereotopic at room temperature, as the barriers for the process of enantiomerization of the seven-membered ring are much higher than expected. It is shown that ring inversion is correlated (but not concerted) with rotation of the amide moiety, as the carbonyl is forced out of conjugation with the nitrogen in the transition state.