7-bromo-5-(2-chlorophenyl)-1-hexyl-1,2,4,5-tetrahydro-3H-1,4-benzodiazepine-2,3-dione | 1381777-43-0

• 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: 7-bromo-5-(2-chlorophenyl)-1-hexyl-1,2,4,5-tetrahydro-3H-1,4-benzodiazepine-2,3-dione
• 英文别名: 7-bromo-5-(2-chlorophenyl)-1-hexyl-1,2,4,5-tetrahydro-3H-1,4-benzodiazepin-2,3-dione；7-bromo-5-(2-chlorophenyl)-1-hexyl-4,5-dihydro-1,4-benzodiazepine-2,3-dione
• CAS: 1381777-43-0
• 化学式: C₂₁H₂₂BrClN₂O₂
• 分子量: 449.775
• InChiKey: HSGDNRNVOZJCDP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-氰基苯甲酸 、 3-羟基芬纳西泮 在 potassium carbonate 作用下， 以 1,4-二氧六环 为溶剂， 以38%的产率得到7-bromo-5-(2-chlorophenyl)-1-hexyl-1,2,4,5-tetrahydro-3H-1,4-benzodiazepine-2,3-dione
  参考文献：
  名称：

  7-溴-5-（2-氯苯基）-3-羟基-1,2-二氢-3h-1,4-苯并二氮杂-2-酮与甲苯磺酸烷基酯烷基化的特点

  摘要：

  在7-溴-5-（2-氯苯基）-3-羟基-1,2-二氢-3H-1,4-苯并二氮杂-2--2-与甲基，己基，十二烷基和鲸蜡基甲苯磺酸酯相互作用时，1-烷基- 7-溴-5-（2-氯苯基）-1,2,4,5-四氢-3H-1,4-苯并二氮杂-2,3-二酮和1-烷基-7-溴-5-（2-获得氯苯基）-3-羟基-1，2-二氢-3H-1，4-苯并二氮杂-1--2-。在甲苯磺酸己酯的情况下，仅形成二酮。用甲苯磺酸甲酯烷基化时，仅形成3-羟基衍生物。结果表明，在pH 14时，1-cetyl和1-dodecyl-3-hydroxy衍生物被完全转化为相应的二酮。通过X射线结构分析确定了化合物的分子和晶体结构。

  DOI：

  10.1007/s10593-010-0436-y

文献信息

• Synthesis and crystal structures of 7-bromo-5-(2′-chloro)phenyl-3-hydroxy-1-methyl-1,2-dihydro-3H-1,4-benzodiazepin-2-one and 7-bromo-5-(2′-chloro)phenyl-1-hexyl-1,2,4,5-tetrahydro-3H-1,4-benzodiazepin-2,3-dione
  作者：Victor Ch. Kravtsov、Marina S. Fonari、Мaria Gdaniec、Victor I. Pavlovsky、Sergei A. Andronati、Ekaterina A. Semenishyna

  DOI：10.1016/j.molstruc.2012.02.071

  日期：2012.6

  Treatment of 7-bromo-5-(2'-chloro)phenyl-3-hydroxy-1,2-dihydro-3H-1,4-benzodiazepin-2-one (1) with methyl or hexyl tosylate resulted in 7-bromo-5-(2'-chloro)phenyl-3-hydroxy-1-methyl-1,2-dihydro-3H-1,4-benzodiazepin-2-one (2) and 7-bromo-5-(2'-chloro)phenyl-1-hexyl-1,2,4,5-tetrahydro-3H-1,4-benzodiazepin-2,3-dione (3). As confirmed by X-ray crystallography, the two products differ not only in the identity of the alkyl substituent in position 1 of the benzodiazepine fragment but also crystallize in different molecular forms resulting from proton migration. This alteration of the molecular structure leads to a significant change in the conformation of the central molecular fragment and influences the assembly mode in the crystal. In 3, centrosymmetric dimers formed via a pair of N-H center dot center dot center dot O hydrogen bonds are further linked into chains via C-Br center dot center dot center dot O=C halogen bond interaction. In turn in 2 there are two symmetry independent molecules, each giving a different set of intermolecular interactions. One of the molecules forms a dimer via O-H center dot center dot center dot O interactions whereas the second one generates chain via C-Br center dot center dot center dot O=C halogen bond that is also assisted by a weak O-H center dot center dot center dot Br hydrogen bond. (C) 2012 Elsevier B.V. All rights reserved.