2,7-dimethyl-2,4-diphenyl-2,3-dihydro-1H-1,5-benzodiazepine

• 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: 2,7-dimethyl-2,4-diphenyl-2,3-dihydro-1H-1,5-benzodiazepine
• 英文别名: 2,7-dimethyl-2,4-diphenyl-1,3-dihydro-1,5-benzodiazepine
• 化学式: C₂₃H₂₂N₂
• 分子量: 326.441
• InChiKey: FSESKCVEFUTZQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3,4-二氨基甲苯 、 苯乙酮 在 nano-γ-Fe2O3-SO3H 作用下， 以 neat (no solvent) 为溶剂， 反应 0.12h， 以90%的产率得到2,7-dimethyl-2,4-diphenyl-2,3-dihydro-1H-1,5-benzodiazepine
  参考文献：
  名称：

  Microwave-Assisted, Solvent Free Preparation of 1,5-Benzodiazepine Derivatives Using Nanomagnetic-Supported Sulfonic Acid as a Recyclable and Heterogeneous Catalyst

  摘要：

  在微波辐照和无溶剂条件下，以纳米-γ-Fe2O3-SO3H 为催化剂，通过邻苯二胺与多种酮的缩合，制备出了一种新的 1,5-苯并二氮杂卓衍生物，收率从良好到极佳。可回收的纳米-γ-Fe2O3-SO3H 具有很高的反应活性，利用外部磁铁很容易从反应混合物中分离出来。这种方法的优点是基于 "绿色化学 "的原则：反应简便快速、无需溶剂、产物易于分离以及良好甚至极佳的产率。

  DOI：

  10.3184/174751915x14473291357176

文献信息

• A green and sustainable approach for the synthesis of 1,5-benzodiazepines and spirooxindoles in one-pot using a MIL-101(Cr) metal–organic framework as a reusable catalyst
  作者：Fillip Kumar Sarkar、Ajay Gupta、Ramen Jamatia、Jasha Momo H. Anal、Amarta Kumar Pal

  DOI：10.1039/d1nj03176g

  日期：——

  MIL-101(Cr) has been efficiently utilized for the synthesis of biologically relevant heterocycles such as 1,5-benzodiazepines and spirooxindoles in one-pot. MIL-101(Cr) was prepared via a solvothermal method and characterized by FT-IR, PXRD, SEM, TEM, EDX, and ICP-OES analysis. Thermogravimetric analysis (TGA) described its high thermal stability. Low catalyst loading, easy separation, reusability, and high

  金属-有机骨架 MIL-101(Cr) 已被有效地用于合成生物相关的杂环，如 1,5-苯二氮卓类和螺环吲哚。MIL-101(Cr) 是通过溶剂热法制备的，并通过 FT-IR、PXRD、SEM、TEM、EDX 和 ICP-OES 分析进行表征。热重分析 (TGA) 描述了其高热稳定性。低催化剂负载、易于分离、可重复使用和高产率是该协议的一些显着特点。无溶剂反应条件 (SFRC) 或水作为溶剂是绿色和可持续工艺开发领域的一些额外优势。
• NBS as an efficient catalyst for the synthesis of 1,5-benzodiazepine derivatives under mild conditions
  作者：Chun-Wei Kuo、Shivaji V. More、Ching-Fa Yao

  DOI：10.1016/j.tetlet.2006.09.128

  日期：2006.11

  Various biologically important 1,5-benzodiazepine derivatives were efficiently synthesized in excellent yields using catalytic amounts of NBS (10 mol %). This inexpensive, nontoxic, and readily available catalyst efficiently catalyzes the condensation of several aromatic as well as aliphatic ketones with substituted o-phenylenediamines.

  使用催化量的NBS（10 mol％），以优异的产率有效地合成了各种生物学上重要的1,5-苯并二氮杂pine衍生物。这种廉价，无毒且易于获得的催化剂有效地催化了几种芳香族以及脂肪族酮与取代的邻苯二胺的缩合。
• Formation of Benzodiazepines and Pyrazinylquinoxalines from Aromatic and Heteroaromatic Ketones via Deoximation
  作者：J.H. Song、S.M. Bae、E.J. Lee、J.H. Cho、D.I. Jung

  DOI：10.14233/ajchem.2020.22639

  日期：——

  However, direct reactions of o-phenylenediamine with oximes (acetone oxime, acetophenone oxime, and benzophenone oxime) as ketone equivalents did not occur. In the course of present investigations, it is found that dichloroamine-T can be an efficient reagent for the conversion of oximes into the corresponding carbonyl compounds. As a part of a research program related to the synthetic study of pharmacologically

  报告指出，用丙酮二甲酸、丙酮和苯乙酮处理邻苯二胺，得到2,4,4-三甲基-3H-5-氢-1,5-苯二氮卓。然而，邻苯二胺与作为酮等价物的肟（丙酮肟、苯乙酮肟和二苯甲酮肟）没有发生直接反应。在目前的研究过程中，发现二氯胺-T可以是将肟转化为相应的羰基化合物的有效试剂。作为与药理学上感兴趣的苯二氮卓化合物的合成研究相关的研究计划的一部分，本文从使用二氯胺-T获得的杂芳酮和丙酮等价物合成1H-1,5-苯二氮卓衍生物。另一方面，当二胺(1,2-苯二胺或1,2-萘二胺)与杂环酮(乙酰基吡啶或乙酰基吡嗪)存在浓的情况下。HCl和SiO2回流，以高收率分离出黄色结晶固体的喹喔啉衍生物
• Synthesis of Hydroxybenzodiazepines with Potential Antioxidant and Antifungal Action
  作者：Elizeu Caiana、Bruno de Veras、Antônia de Souza、Neide Queiroz

  DOI：10.21577/0103-5053.20200217

  日期：——

  compounds. The novelty of this study encompasses the synthesis of new hydroxylated analogs of 1,5-benzodiazepine together with the evaluation of their biological potential as antioxidants and antifungals candidates. Additionally, the reported antifungal activity against fungi of the Sporothrix schenckii complex inaugurates an unprecedented property for this class of compounds. The results of biological

  苯二氮卓类衍生物是氮杂环化合物，具有各种工业、合成和药用应用。因此，对这些杂环化合物的新型、选择性和有效生产的改进的每一项努力都是有充分潜力的。这项研究的创新之处在于合成了新的1,5-苯二氮卓的羟基类似物，并评估了它们作为抗氧化剂和抗真菌候选药物的生物潜力。此外，报道的抗真菌活性表明，对于斯伯拉氏孢子囊菌复合体的真菌开展了这一类化合物的前所未有的特性。生物活性测定结果表明，新型的2,7-二甲基-2,4-双(4-羟基苯基)-2,3-二氢-1H-1,5-苯二氮卓对斯伯拉氏属的所有真菌菌株具有高抗真菌活性和出色的总抗氧化能力。此外，计算机模拟研究表明，羟基衍生物具有最佳的水溶性和细胞渗透性，使它们在与常用于斯伯拉氏病治疗的商业抗真菌伊曲康唑相比更具优势。
• Polyfluorinated–zinc(II)phthalocyanine complex immobilized on silica: A novel, highly selective and recyclable inorganic–organic hybrid catalyst for the synthesis of biologically important 1,5-benzodiazepines
  作者：R.K. Sharma、Shikha Gulati、Amit Pandey

  DOI：10.1016/j.ica.2012.11.012

  日期：2013.3

  A novel, efficient and recyclable catalyst was prepared by covalent grafting of polyfluorinatedzinc(II)phthalocyanine complex onto functionalized silica gel. The activity of the catalyst was investigated for the solvent-free synthesis of 1,5-benzodiazepines at room temperature. The immobilized catalyst was characterized by elemental analysis (CHN), diffuse reflectance UV-Vis spectroscopy, solid-state C-13 CPMAS and Si-29 CPMAS NMR spectroscopy, X-ray diffraction (XRD), scanning electron microscopy (SEM), BET surface area analysis, energy dispersive X-ray fluorescence (ED-XRF), Fourier transform Infrared (FT-IR) and atomic absorption spectroscopy (AAS) techniques. Short reaction time, mild reaction conditions, high turnover numbers, and easy recovery and reusability of the catalyst make this method a novel, economic and waste-free chemical process for the synthesis of biologically important 1,5-benzodiazepines. (C) 2012 Elsevier B. V. All rights reserved.