奥卡西平杂质8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 中文名称: 奥卡西平杂质8
• 英文名称: trans-10,11-dibromo-10,11-dihydro-5H-dibenzazepine-5-carboxamide
• 英文别名: (5S,6S)-5,6-dibromo-5,6-dihydrobenzo[b][1]benzazepine-11-carboxamide
• 化学式: C₁₅H₁₂Br₂N₂O
• 分子量: 396.081
• InChiKey: OQUVNEXIZHZXGS-KBPBESRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  奥卡西平杂质8 在 高氯酸四乙基铵 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以92%的产率得到卡马西平
  参考文献：
  名称：

  Jugelt; Gessner, Pharmazie, 1992, vol. 47, # 6, p. 426 - 432

  摘要：

  DOI：
• 作为产物：
  描述：

  卡马西平 在 溴 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 以90%的产率得到奥卡西平杂质8
  参考文献：
  名称：

  The detection of ionic intermediates during the bromination of 5H-dibenz[b,f]azepine-5-carboxamide in 1,2-dichloroethane

  摘要：

  The bromination of 5H-dibenz[b,f]azepine-5-carboxamide (carbamazepine) (1) in 1,2-dichloroethane gives only the trans-dibromide 2. The reaction, followed spectrophotometrically, obeys a third-order rate law (second-order in Br2), but the value of k3 changes considerably depending on the monitoring wavelength. It is shown that this is due to the presence of reversibly formed Br3- salt intermediates, that make a more important contribution to the absorbance in the lower wavelength range of the monitored 360-540 nm region. A significant conductivity is also measured during the course of the bromination. Both spectrophotometric and conductimetric measurements are consistent with the presence of Br3- salt intermediates at a maximum concentration amounting to ca. 2% of that of the initial reagents. The structure of dibromide 2, determined by X-ray diffraction, shows a considerable angle strain at carbons bearing bromine. This strain is responsible for an easy spontaneous debromination of 2, as well as for a relatively high barrier for the formation of 2 from the bromonium-tribromide intermediate, that makes possible the accumulation of the intermediate itself during the bromination of 1.

  DOI：

  10.1039/p29920000637