4-(2-hydroxyphenyl)-2-(4-methoxyphenyl)-2,3-dihydro-1H-benzo[b]1,4-diazepine | 1058163-34-0

• 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: 4-(2-hydroxyphenyl)-2-(4-methoxyphenyl)-2,3-dihydro-1H-benzo[b]1,4-diazepine
• 英文别名: 2-(2,3-dihydro-2-(4-methoxyphenyl)-1H-benzo[b][1,5]diazepin-4-yl)phenol；4-(2-hydroxyphenyl)-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzodiazepine；2-[2-(4-methoxyphenyl)-2,3-dihydro-1H-1,5-benzodiazepin-4-yl]phenol
• CAS: 1058163-34-0
• 化学式: C₂₂H₂₀N₂O₂
• 分子量: 344.413
• InChiKey: YQNLMNMIYVMSLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  53.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-羟基-4'-甲氧基查尔酮 、 邻苯二胺 在 erbium(III) triflate 作用下， 以 乙腈 为溶剂， 反应 3.0h， 以98%的产率得到4-(2-hydroxyphenyl)-2-(4-methoxyphenyl)-2,3-dihydro-1H-benzo[b]1,4-diazepine
  参考文献：
  名称：

  1,5-Benzoheteroazepines through eco-friendly general condensation reactions

  摘要：

  Condensation reactions of o-phenylenediamine and 2 equiv of acetone produce biaryl-substituted 1, 5-benzodiazepines. The synthetic protocol shows general applicability since similar reaction of o-phenylenediamines, o-aminophenol, and o-aminothiophenol with ketones or chalcones leads to formation of functionalized 1,5-benzoheteroazepines in good to excellent yields. The synthetic protocol fulfills many green-chemical requirements using simple MW-assistance to promote the activation of ketones and the eco-compatible Er(III) triflate as activator of chalcones. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.06.029

文献信息

• Efficient and Eco-friendly Syntheses of 1,5-Benzothiazepines and 1,5-Benzodiazepines Catalyzed by [<i>Hmim</i>][NO₃] under Mild Conditions
  作者：Hossein Loghmani-Khouzani、Panteha Tamjidi、Iraj Mohammadpoor-Baltork、Marzieh Yaeghoobi、Noorsaadah Abd. Rahman、Ahmad Reza Khosropour、Majid Moghadam、Shahram Tangestaninejad、Valiolah Mirkhani、Mohammad Hossein Habibi、Ayana Kashima、Takayoshi Suzuki

  DOI：10.1002/jhet.1827

  日期：2014.1

  Crystal structures of a new thiazepine and diazepine (seven‐membered rings) have also been determined and compared with thiazine (six‐membered ring). In this method, N‐methylimidazolium nitrate [Hmim][NO3] has been used as a catalyst that acts as an environmental friendly system.

  本文介绍了1,5-苯并噻氮杂类和1,5-苯并二氮杂类衍生物的合成方法和反应机理。在这项研究中，已经用新方法制备了36种噻嗪类和二氮杂品（大多数是新的），并通过分光镜方法对其结构进行了表征。还确定了新的噻氮平和二氮杂（七元环）的晶体结构，并将其与噻嗪（六元环）进行了比较。在此方法中，硝酸N甲基咪唑鎓盐[ Hmim ] [NO 3 ]被用作催化剂，对环境无害。
• Ga(OTf)3-promoted condensation reactions for 1,5-benzodiazepines and 1,5-benzothiazepines
  作者：Xiang-Qiang Pan、Jian-Ping Zou、Zhi-Hao Huang、Wei Zhang

  DOI：10.1016/j.tetlet.2008.06.082

  日期：2008.9

  Condensation reactions of o-phenylenediamine and two equivalents of acetophenone under gallium(III) triflate catalysis produce biaryl-substituted 1,5-benzodiazepines. Similar reactions of o-phenylenediamine or o-aminothiophenol and o-hydroxy chalcones lead to formation of functionalized 1,5-benzodiazepines and 1,5-benzothiazepines in good to excellent yields. The ortho-hydoxy group of chalcones is crucial for this unprecedented condensation process. (C) 2008 Elsevier Ltd. All rights reserved.
• SOLVENT FREE OXALIC ACID CATALYZED SYNTHESIS OF 1,5-BENZODIAZEPINES
  作者：ANIKET P SARKATE、JAIPRAKASH N SANGSHETTI、NANASAHEB B DHARBALE、AJINKYA P SARKATE、PRAVIN S WAKTE、DEVANAND B SHINDE

  DOI：10.4067/s0717-97072013000400064

  日期：——

  In the present study 1, 5-benzodiazepines were synthesized from a range of alpha, beta-unsaturated ketones and o-phenylendiamine using oxalic acid 10 mol% as a catalyst under solvent free conditions. The yields of the present method are better than the reported method which explains effectiveness of oxalic acid catalyst. The cost effective, resourceful, undemanding and environment friendly are the advantageous aspects of this method.