1H-1,5-苯并二氮卓,7-氯-2,3-二氢-2-甲基-2,4-二苯基- | 105273-79-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 中文名称: 1H-1,5-苯并二氮卓,7-氯-2,3-二氢-2-甲基-2,4-二苯基-
• 英文名称: 2-methyl-2,4-diphenyl-7-chloro-2,3-dihydro-1H-1,5-benzodiazepine
• 英文别名: 7-chloro-2-methyl-2,4-diphenyl-2,3-dihydro-1H-benzo[b][1,4]diazepine；7-chloro-2-methyl-2,4-diphenyl-2,3-dihydro-1H-1,5-benzodiazepine；2-methyl-2,4-diphenyl-2,3-dihydro-7-chloro-1H-1,5-；7-chloro-2-methyl-2,4-diphenyl-1,3-dihydro-1,5-benzodiazepine
• CAS: 105273-79-8
• 化学式: C₂₂H₁₉ClN₂
• 分子量: 346.859
• InChiKey: JXZJKYKQBUEIMU-UHFFFAOYSA-N

物化性质

• 沸点：
  501.3±50.0 °C(Predicted)
• 密度：
  1.17±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  24.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3,5-tri-O-benzoyl-β-D-ribofuranosyl bromide 、 1H-1,5-苯并二氮卓,7-氯-2,3-二氢-2-甲基-2,4-二苯基- 反应 4.0h， 以80%的产率得到(2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(7-chloro-2-methyl-2,4-diphenyl-2,3-dihydro-1H-benzo[b][1,4]diazepin-1-yl)tetrahydrofuran-3,4-diyl dibenzoate
  参考文献：
  名称：

  Yadav, Ashok K.; Kumar, Manoj; Yadav, Tripti, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2010, vol. 49, # 4, p. 461 - 468

  摘要：

  DOI：
• 作为产物：
  描述：

  苯乙酮肟 在 二氯胺T 、 水 、 silica gel 作用下， 以 乙腈 为溶剂， 反应 10.33h， 生成 1H-1,5-苯并二氮卓,7-氯-2,3-二氢-2-甲基-2,4-二苯基- 、 2-methyl-2,4-diphenyl-8-chloro-2,3-dihydro-1H-1,5-benzodiazepine
  参考文献：
  名称：

  通过脱肟化从芳香酮和杂芳香酮形成苯二氮卓类和吡嗪基喹喔啉

  摘要：

  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

  DOI：

  10.14233/ajchem.2020.22639

文献信息

• Silica gel-supported sulfuric acid catalyzed synthesis of 1,5-benzodiazepine derivatives
  作者：D. Shobha、M. Adharvana Chari、K. Mukkanti、K. H. Ahn

  DOI：10.1002/jhet.174

  日期：2009.9

  Silica gel-supported sulfuric acid has been found to be an efficient catalyst for the synthesis of 1,5-benzodiazepines from o-phenylenediamine and ketones in acetonitrile solvent. This method is simple, effective, and environmentally friendly and gives better yields. Compared to the classical reaction conditions, this new method consistently has the advantage of excellent yields (80–97%) and short

  二氧化硅凝胶支持硫酸已被发现是用于1,5-苯并二氮杂将来自合成的有效的催化剂在乙腈溶剂中的邻苯二胺和酮。该方法简单，有效，环境友好，收率更高。与经典反应条件相比，这种新方法始终具有在室温下具有出色的收率（80–97％）和较短的反应时间（30–150分钟）的优势。J.杂环化​​学，（2009）。
• 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。
• 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.
• Gold(I)-Catalyzed Synthesis of 1,5-Benzodiazepines Directly from <i>o</i>-Phenylenediamines and Alkynes
  作者：Jianqiang Qian、Yunkui Liu、Jianhai Cui、Zhenyuan Xu

  DOI：10.1021/jo300543n

  日期：2012.5.4

  A unique gold(I)-catalyzed highly atom-economic synthesis of 1,5-benzodiazepines directly from o-phenylenediamines and alkynes has been achieved for the first time.