1,4,5-trimethyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-one | 78679-16-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: 1,4,5-trimethyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-one
• 英文别名: 1,3,4,5-Tetrahydro-1,4,5-trimethyl-2H-1,5-benzodiazepin-2-one；1,2,5-trimethyl-2,3-dihydro-1,5-benzodiazepin-4-one
• CAS: 78679-16-0
• 化学式: C₁₂H₁₆N₂O
• 分子量: 204.272
• InChiKey: XFVPEPYIFNNMHP-UHFFFAOYSA-N

物化性质

• 沸点：
  386.6±35.0 °C(Predicted)
• 密度：
  1.060±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 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：
  23.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-甲基-1,3,4,5-四氢-2H-1,5-苯并二氮杂卓-2-酮 、 碘甲烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以0.2 g的产率得到4,5-dimethyl-2,3,4,5-tetrahydro-1H-1,5-benzodiazepin-2-one
  参考文献：
  名称：

  Nuclear magnetic resonance spectra of psychotherapeutic agents. V*—conformational analysis of 1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-ones

  摘要：

  AbstractThe conformational analysis of biologically active lofendazam (7‐chloro‐5‐phenyl‐1,3,4,5‐tetrahydro‐2H‐1,5‐benzodiazepin‐2‐one) is carried out by means of lanthanide shift reagent assisted 1H NMR spectroscopy: the lanthanide induced shift computer simulation suggests that in deuteriochloroform the heterocyclic ring of lofendazam assumes a cycloheptene‐like chair conformation, where 1‐N moves away from trigonal stereochemistry to a very flattened pyramidal structure. At room temperature the conformational equilibrium is markedly shifted (85%) towards the conformer showing pseudoaxial H‐1 and 5‐Ph. The remarkable influence of steric requirements in controlling conformation, and the importance of 3‐ and/or 4‐methyl groups in hindering the ring inversion at room temperature, have been verified by conformational analysis of suitable analogous 1,3,4,5‐tetraydro‐2H‐1,5‐benzodiazepin‐2‐ones.

  DOI：

  10.1002/mrc.1270150414

文献信息

• Nuclear magnetic resonance spectra of psychotherapeutic agents. V*—conformational analysis of 1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-ones
  作者：M. C. Aversa、P. Giannetto、G. Romeo、P. Ficarra、M. G. Vigorita

  DOI：10.1002/mrc.1270150414

  日期：1981.4

  AbstractThe conformational analysis of biologically active lofendazam (7‐chloro‐5‐phenyl‐1,3,4,5‐tetrahydro‐2H‐1,5‐benzodiazepin‐2‐one) is carried out by means of lanthanide shift reagent assisted 1H NMR spectroscopy: the lanthanide induced shift computer simulation suggests that in deuteriochloroform the heterocyclic ring of lofendazam assumes a cycloheptene‐like chair conformation, where 1‐N moves away from trigonal stereochemistry to a very flattened pyramidal structure. At room temperature the conformational equilibrium is markedly shifted (85%) towards the conformer showing pseudoaxial H‐1 and 5‐Ph. The remarkable influence of steric requirements in controlling conformation, and the importance of 3‐ and/or 4‐methyl groups in hindering the ring inversion at room temperature, have been verified by conformational analysis of suitable analogous 1,3,4,5‐tetraydro‐2H‐1,5‐benzodiazepin‐2‐ones.