2-(4-cyanophenyl)-4-phenyl-2,3-dihydrobenzo[b][1,4]thiazepine | 86602-77-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并硫氮卓类
• 英文名称: 2-(4-cyanophenyl)-4-phenyl-2,3-dihydrobenzo[b][1,4]thiazepine
• 英文别名: 4-(4-Phenyl-2,3-dihydro-1,5-benzothiazepin-2-yl)benzonitrile
• CAS: 86602-77-9
• 化学式: C₂₂H₁₆N₂S
• 分子量: 340.448
• InChiKey: YGJQZBMZJGUPJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  61.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-cyanophenyl)-4-phenyl-2,3-dihydrobenzo[b][1,4]thiazepine 、 phenylhydroxamoyl chloride 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以52%的产率得到3a,4-dihydro-1,3a-diphenyl-5-(4-cyanophenyl)-5H-<1,2,4>oxadiazolo<5,4-d><1,5>benzothiazepine
  参考文献：
  名称：

  5H-[1,2,4]Oxadiazolo[5,4-d][1,5]benzothiazepines as anticonvulsant agents in DBA/2 mice

  摘要：

  A series of 3a,4-dihydro-5H-[1,2,4]oxadiazolo[5,4-d] [1,5]benzothiazepines have been synthesized by 1,3-dipolar cycloaddition reaction of benzonitriloxide to the C=N double bond of 1,5-benzothiazepine derivatives, and the stereochemical features of compounds obtained have been determined by NMR spectroscopy. The results of evaluation of their activity in preventing seizures induced by audiogenic stimulation in DBA/2 mice are also reported and discussed. The 5-(4-bromophenyl)1,3-diphenyl derivative 3b, the most active compound of the series, is over 20 times more active than the parent benzothiazepine Ib and shows an activity comparable to clobazam and better than desmethylclobazam.

  DOI：

  10.1016/0223-5234(96)88311-5
• 作为产物：
  描述：

  4-溴苯腈 、 (+/-)-1-苯基-2-丙炔-1-醇 、 2-氨基苯硫醇 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 以67%的产率得到2-(4-cyanophenyl)-4-phenyl-2,3-dihydrobenzo[b][1,4]thiazepine
  参考文献：
  名称：

  A Novel 1,5-Benzoheteroazepine Synthesis via a One-Pot Coupling−Isomerization−Cyclocondensation Sequence

  摘要：

  2,4-Di(hetero)aryl substituted 2,3-dihydro 1,5-benzoheteroazepines (hetero = NH, O, S) can be readily sythesized in a one-pot process initiated by a coupling-isomerization sequence of an electron poor (hetero)aryl halide and a terminal propargyl alcohol subsequently followed by a cyclocondensation with 2-amino, 2-hydroxy, or 2-mercapto anilines. In addition, the structures were established unambiguously by an X-ray structure analysis of 7a.

  DOI：

  10.1021/ol006721k

文献信息

• One-pot syntheses of dihydro benzo[b][1,4]thiazepines and -diazepines via coupling–isomerization–cyclocondensation sequences
  作者：Roland U. Braun、Thomas J.J. Müller

  DOI：10.1016/j.tet.2004.08.001

  日期：2004.10

  2,4-Di(hetero)aryl substituted 2,3-dihydro benzo[b][1,4]heteroazepines 7 and 9 (hetero=S, NH) can be readily synthesized in a one-pot process initiated by a coupling-isomerization sequence of an electron poor (hetero)aryl halide 4 and a terminal propargyl alcohol 5 subsequently followed by a cyclocondensation with 2-mercapto or 2-amino anilines 6 or 8, respectively. In addition, the structures were established unambiguously by an X-ray structure analysis of 9b. (C) 2004 Elsevier Ltd. All rights reserved.