2-(4-nitrophenyl)-4-phenyl-2,3-dihydrobenzo[b][1,4]diazepine | 75220-79-0

• 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: 2-(4-nitrophenyl)-4-phenyl-2,3-dihydrobenzo[b][1,4]diazepine
• 英文别名: 2-(4-nitrophenyl)-4-phenyl-2,3-dihydro-1H-1,5-benzodiazepine
• CAS: 75220-79-0
• 化学式: C₂₁H₁₇N₃O₂
• 分子量: 343.385
• InChiKey: JBCDOBWKOOOYRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-nitrophenyl)-4-phenyl-2,3-dihydrobenzo[b][1,4]diazepine 在 盐酸 作用下， 以 甲醇 为溶剂， 以59%的产率得到2-(4-硝基苯基)-1H-苯并咪唑
  参考文献：
  名称：

  Benzimidazole rearrangement of dihydrobenzodiazepines

  摘要：

  DOI：

  10.1007/bf00513270
• 作为产物：
  描述：

  (E)-3-(4-nitrophenyl)-1-phenylprop-2-en-1-one 、 邻苯二胺 在 aluminum oxide 作用下， 反应 3.0h， 以43%的产率得到2-(4-nitrophenyl)-4-phenyl-2,3-dihydrobenzo[b][1,4]diazepine
  参考文献：
  名称：

  无机载体上 1,5-苯并噻嗪类和苯二氮类的无溶剂合成

  摘要：

  摘要 1,5-苯并二氮杂和 1,5-苯二氮卓类化合物在无溶剂条件下由查耳酮和邻氨基苯硫酚或邻苯二胺在无机载体存在下合成。发现硅胶是合成 1,5-苯并噻嗪类药物的有效载体，而氧化铝对合成 1,5-苯二氮卓类药物有效。

  DOI：

  10.1081/scc-120034159

文献信息

• [BPy]HSO₄Acidic Ionic Liquid as a Novel, Efficient, and Environmentally Benign Catalyst for Synthesis of 1,5‐Benzodiazepines under Mild Conditions
  作者：Yuying Du、Fuli Tian、Wenzhi Zhao

  DOI：10.1080/00397910600616602

  日期：2006.7

  Abstract A novel and simple ionic liquid methodology for the synthesis of 1,5‐benzodiazepines is described. 1‐Butylpyridinium hydrogen sulphate ([BPy]HSO4), an acidic room‐temperature ionic liquid, as a novel and efficient catalyst, was synthesized and used in the preparation of a series of 1,5‐benzodiazepine derivatives by the reaction of o‐phenylenediamine with chalcones under mild conditions. This

  摘要描述了一种用于合成 1,5-苯二氮卓类药物的新颖且简单的离子液体方法。1-丁基吡啶鎓硫酸氢盐 ([BPy]HSO4) 是一种酸性室温离子液体，作为一种新型高效催化剂，被合成并用于通过 o- 反应制备一系列 1,5-苯二氮卓衍生物。苯二胺与查耳酮在温和条件下。该方法简单、高效、环保、经济、不含有毒催化剂，并且对1,5-苯二氮卓类的形成具有良好的收率
• Synthesis and inhibition studies towards the discovery of benzodiazepines as potential antimalarial compounds
  作者：Drista Sharma、Abhishek Pareek、Hemant Arya、Rani Soni、Praveen Rai、Akhil Agrawal、Surendra Nimesh、Diwakar Kumar、Srinivasarao Yaragorla、Tarun Kumar Bhatt

  DOI：10.1016/j.exppara.2022.108411

  日期：2022.12

  apicoplast in the survival of the parasite. In this study, we present the rational design strategy employing sustainable catalysis for the synthesis of benzodiazepine (BDZ) conformers followed by their biological evaluation as prospective inhibitors against the potential target of the IPP pathway, 1-deoxy-D-xylulose-5-phosphatereductoisomerase (DXR). The study reported the inhibitory profile of 8c and 6d

  基于靶标的针对顶端质体（一种非常重要的细胞器）的治疗方法的发现是一个压倒一切的观点。MEP 通路是一种经认可的药物靶标，可深入了解顶端体在寄生虫生存中的重要性。在这项研究中，我们提出了采用可持续催化合成苯并二氮卓 (BDZ) 构象异构体的合理设计策略，然后将其作为针对 IPP 途径潜在靶标 1-脱氧-D-木酮糖-5-磷酸还原异构酶的前瞻性抑制剂进行生物学评估(DXR)。该研究报告了 8c 和 6d 对寄生虫发育红细胞阶段唯一药物靶标的典型步骤的抑制作用。
• 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.
• New aspects of the chemistry of 2,3-dihydro-1H-1,5-benzodiazepine
  作者：V. D. Orlov、N. N. Kolos、F. G. Yaremenko、V. F. Lavrushin

  DOI：10.1007/bf00561358

  日期：1980.5
• A Novel 1,5-Benzoheteroazepine Synthesis via a One-Pot Coupling−Isomerization−Cyclocondensation Sequence
  作者：Roland U. Braun、Kirsten Zeitler、Thomas J. J. Müller

  DOI：10.1021/ol006721k

  日期：2000.12.1

  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.