2-(2-phenyl-2,3-dihydro-1H-1,5-benzodiazepin-4-yl)phenol | 41458-53-1

• 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: 2-(2-phenyl-2,3-dihydro-1H-1,5-benzodiazepin-4-yl)phenol
• 英文别名: 2-(2'-hydroxyphenyl)-4-phenyl-3H-1,5-benzodiazepine；2-(4-phenyl-3H-benzo[b][1,4]diazepin-2-yl)-phenol；2-(4-phenyl-3H-1,5-benzodiazepin-2-yl)phenol；2-(2-phenyl-3H-1,5-benzodiazepin-4-yl)phenol
• CAS: 41458-53-1
• 化学式: C₂₁H₁₆N₂O
• mdl: MFCD02110748
• 分子量: 312.371
• InChiKey: KAHVHCFQIWBPBS-UHFFFAOYSA-N

物化性质

• 熔点：
  181 °C(Solv: ethanol (64-17-5))
• 沸点：
  477.4±45.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  45
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (2E)-1-(2-羟基苯基)-3-苯基-2-丙烯-1-酮 、 邻苯二胺 在 sodium acetate 作用下， 以 二甲基亚砜 为溶剂， 以86%的产率得到2-(2-phenyl-2,3-dihydro-1H-1,5-benzodiazepin-4-yl)phenol
  参考文献：
  名称：

  An Efficient Synthesis of 1,5-Thiadiazepines and 1,5-Benzodiazepines by Microwave-Assisted Heterocyclization

  摘要：

  A novel and efficient method for the synthesis of substituted thiazepines and diazepines has been developed. A simple one-pot reaction of chalcones 1a-f with 1-amino-2-mercapto-5-phenyl-1,3,4-triazole and o-phenylenediamine in the presence of a catalytic amount of sodium acetate under microwave irradiation gave 2-(3,8-diphenyl-7,8-dihydro[1,2,4]triazolo[3,4-b][1,3,4]thiadiazepin-6-yl)phenoles 2a-f and 2-(2-phenyl-2,3-dihydro-1H-1,5-benzodiazepin-4-yl)phenoles 3a-f, respectively. The structure of all the synthesized compounds was elucidated on the basis of elemental analysis, IR, H-1 and C-13 NMR, and mass spectral data.

  DOI：

  10.1080/10426500600864775

文献信息

• Preyssler catalyst-promoted rapid, clean, and efficient condensation reactions for 3H-1,5-benzodiazepine synthesis in solvent-free conditions
  作者：Gustavo A. Pasquale、Diego M. Ruiz、Jorge L. Jios、Juan C. Autino、Gustavo P. Romanelli

  DOI：10.1016/j.tetlet.2013.09.101

  日期：2013.11

  A simple, convenient, and environmentally benign synthesis of 1,5-benzodiazepines is developed by condensing different o-phenylenediamines and 1,3-aryl-1,3-propanodiones. The reaction is catalyzed by a Preyssler (NaH14P5W30O110, HPA) heteropolyacid as a safe, clean, and recyclable catalyst. The method is operationally simple and provides access to a variety of 1,5-benzodiazepines in good to excellent yields. (C) 2013 Elsevier Ltd. All rights reserved.
• An Efficient Synthesis of 1,5-Thiadiazepines and 1,5-Benzodiazepines by Microwave-Assisted Heterocyclization
  作者：Gundibasappa K. Nagaraja、Vijayavittala P. Vaidya、Koodamara Sheshappa Rai、Kittappa M. Mahadevan

  DOI：10.1080/10426500600864775

  日期：2006.12.1

  A novel and efficient method for the synthesis of substituted thiazepines and diazepines has been developed. A simple one-pot reaction of chalcones 1a-f with 1-amino-2-mercapto-5-phenyl-1,3,4-triazole and o-phenylenediamine in the presence of a catalytic amount of sodium acetate under microwave irradiation gave 2-(3,8-diphenyl-7,8-dihydro[1,2,4]triazolo[3,4-b][1,3,4]thiadiazepin-6-yl)phenoles 2a-f and 2-(2-phenyl-2,3-dihydro-1H-1,5-benzodiazepin-4-yl)phenoles 3a-f, respectively. The structure of all the synthesized compounds was elucidated on the basis of elemental analysis, IR, H-1 and C-13 NMR, and mass spectral data.