2-[4-(2,6-Dimethoxy-phenyl)-3H-benzo[b][1,4]diazepin-2-yl]-phenol | 197803-93-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-[4-(2,6-Dimethoxy-phenyl)-3H-benzo[b][1,4]diazepin-2-yl]-phenol
• 英文别名: 2-[4-(2,6-dimethoxyphenyl)-3H-1,5-benzodiazepin-2-yl]phenol
• CAS: 197803-93-3
• 化学式: C₂₃H₂₀N₂O₃
• 分子量: 372.423
• InChiKey: KONQPBOUHQOHKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  63.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[4-(2,6-Dimethoxy-phenyl)-3H-benzo[b][1,4]diazepin-2-yl]-phenol 在 三溴化硼-二甲基硫醚 三溴甲基硫化硼 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 6.0h， 以89%的产率得到2-(2'-hydroxyphenyl)-4-(2''-hydroxy-6''-methoxyphenyl)-3H-1,5-benzodiazepine
  参考文献：
  名称：

  Study of the conformational equilibria of some 2-(2?-hydroxyphenyl)-4-aryl-3H-1,5-benzodiazepines using1H,13C, and15N NMR spectroscopy

  摘要：

  Variable temperature H-1 NMR experiments of 2-(2'-hydroxyphenyl)-4-phenyl-3H-1,5-benzodiazepine (5a) and its derivatives 5d and 5e were carried out in order to investigate the conformational behaviour of these compounds. The Delta G* values for the ring inversion barriers of 5a and 5d are ca. 52 kJ/mol, i.e. they do not differ significantly as compared to analogous compounds without phenolic OH group(s). This indicates that the hydrogen bond has not to be opened during the inversion process. In 5e the barrier is about 2-3 kJ/mol higher which can be explained by steric interference between the additional methoxy group and the H-3 atoms during ring inversion. (NNMR)-N-15 data which can be discussed in terms of hydrogen bond strength support this interpretation.

  DOI：

  10.1007/bf00807594
• 作为产物：
  描述：

  (2-acetylphenyl) 2,6-dimethoxybenzoate 在 五氯硝基苯 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 6.0h， 生成 2-[4-(2,6-Dimethoxy-phenyl)-3H-benzo[b][1,4]diazepin-2-yl]-phenol
  参考文献：
  名称：

  Study of the conformational equilibria of some 2-(2?-hydroxyphenyl)-4-aryl-3H-1,5-benzodiazepines using1H,13C, and15N NMR spectroscopy

  摘要：

  Variable temperature H-1 NMR experiments of 2-(2'-hydroxyphenyl)-4-phenyl-3H-1,5-benzodiazepine (5a) and its derivatives 5d and 5e were carried out in order to investigate the conformational behaviour of these compounds. The Delta G* values for the ring inversion barriers of 5a and 5d are ca. 52 kJ/mol, i.e. they do not differ significantly as compared to analogous compounds without phenolic OH group(s). This indicates that the hydrogen bond has not to be opened during the inversion process. In 5e the barrier is about 2-3 kJ/mol higher which can be explained by steric interference between the additional methoxy group and the H-3 atoms during ring inversion. (NNMR)-N-15 data which can be discussed in terms of hydrogen bond strength support this interpretation.

  DOI：

  10.1007/bf00807594