4-phenyl-4,5-dihydrobenzo[f][1,4]oxazepin-3(2H)-thione | 1095706-67-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶嗪类
• 英文名称: 4-phenyl-4,5-dihydrobenzo[f][1,4]oxazepin-3(2H)-thione
• 英文别名: 4-Phenyl-4,5-dihydrobenzo[f][1,4]oxazepin-3(2h)-thione；4-phenyl-5H-1,4-benzoxazepine-3-thione
• CAS: 1095706-67-4
• 化学式: C₁₅H₁₃NOS
• 分子量: 255.34
• InChiKey: IWWIOPXZKWLWDD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  44.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  Phenol, 2-[(E)-(phenylimino)methyl]- 在 sodium tetrahydroborate 、 tetraphosphorus decasulfide 、 三乙胺 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 5,5-dimethyl-1,3-cyclohexadiene 、 乙醇 、 苯 为溶剂， 反应 7.0h， 生成 4-phenyl-4,5-dihydrobenzo[f][1,4]oxazepin-3(2H)-thione
  参考文献：
  名称：

  Synthesis and structure–antibacterial activity relationship studies of 4-substituted phenyl-4,5-dihydrobenzo[f][1,4]oxazepin-3(2H)-thiones

  摘要：

  The synthesis and characterization of a series of 4-substituted phenyl-4,5-dihydrobenzo[f][1,4]oxazepin-3(2H)-thiones were presented. Preliminary in vitro antimicrobial activity of the compounds was assessed against a panel of microorganisms including S. aureus, E. faecalis, P. aeruginosa, E. coli, and C. albicans. Some of the compounds exhibited significantly in vitro antimicrobial activity. The pMIC values were correlated with physicochemical descriptors: Hammett substituent constants (sigma (m) and sigma (p) ) and the lipophilic constant (pi). One statistical significant 2D-QSAR model was obtained with para-substituted compounds. The pMIC values were also correlated with some theoretical descriptors as independent variables and four statistical significant 2D-QSAR models were also obtained with meta-substituted compounds.

  DOI：

  10.1007/s00044-010-9457-4

文献信息

• Synthesis, infrared spectral studies and theoretical calculations of 4-phenyl-4,5-dihydrobenzo[f][1,4]oxazepin-3(2H)-one (thione)
  作者：Hikmet Agirbas、Seda Sagdinc、Fatma Kandemirli、Berat Kemal

  DOI：10.1016/j.molstruc.2008.05.023

  日期：2008.12

  gave 2-((phenylamino)methyl)phenol (3) which was reacted with chloroacetyl chloride to give 2-chloro-N-(2-hydroxybenzyl)-N-phenylacetamide (4). Compound (4) was cyclized to 4phenyl-4,5-dihydrobenzo[f][1,4]oxazepin-3(2H)-one (5) by NaOH in ethanol solution. The treatment of compound (5) with P2S5 gave corresponding 4-phenyl-4,5-dihydrobenzo[f][1,4]oxazepin-3(2H)-thione (6). The structures of (5) and (6)

  水杨醛 (1) 与苯胺反应得到 2-[(E)-(苯基亚氨基)甲基]苯酚 (2)。用NaBH 4 还原(2)得到2-((苯氨基)甲基)苯酚(3)，其与氯乙酰氯反应得到2-氯-N-(2-羟基苄基)-N-苯基乙酰胺(4)。通过乙醇溶液中的NaOH将化合物(4)环化为4苯基-4,5-二氢苯并[f][1,4]恶氮杂-3(2H)-酮(5)。用P2S5处理化合物(5)得到相应的4-苯基-4,5-二氢苯并[f][1,4]氧氮杂-3(2H)-硫酮(6)。(5)和(6)的结构由 1 H NMR和IR光谱确定。(5) 和 (6) 的优化结构参数和振动频率是通过 DFT 计算的，具有 6-31G(d,p) 基组。采用标准3-21G基组的RHF研究了环化反应的机理。2008 Elsevier BV 版权所有。
• Synthesis and structure–antibacterial activity relationship studies of 4-substituted phenyl-4,5-dihydrobenzo[f][1,4]oxazepin-3(2H)-thiones
  作者：Hikmet Agirbas、Berat Kemal、Fatma Budak

  DOI：10.1007/s00044-010-9457-4

  日期：2011.11

  The synthesis and characterization of a series of 4-substituted phenyl-4,5-dihydrobenzo[f][1,4]oxazepin-3(2H)-thiones were presented. Preliminary in vitro antimicrobial activity of the compounds was assessed against a panel of microorganisms including S. aureus, E. faecalis, P. aeruginosa, E. coli, and C. albicans. Some of the compounds exhibited significantly in vitro antimicrobial activity. The pMIC values were correlated with physicochemical descriptors: Hammett substituent constants (sigma (m) and sigma (p) ) and the lipophilic constant (pi). One statistical significant 2D-QSAR model was obtained with para-substituted compounds. The pMIC values were also correlated with some theoretical descriptors as independent variables and four statistical significant 2D-QSAR models were also obtained with meta-substituted compounds.