2,2,4-trimethyl-7-nitro-2,3-dihydro-1H-benzo[b][1,4]diazepine

• 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: 2,2,4-trimethyl-7-nitro-2,3-dihydro-1H-benzo[b][1,4]diazepine
• 英文别名: 2,2,4-trimethyl-7-nitro-2,3-dihydro-1H-1,5-benzodiazepine；2,2,4-trimethyl-7-nitro-1,3-dihydro-1,5-benzodiazepine
• 化学式: C₁₂H₁₅N₃O₂
• 分子量: 233.27
• InChiKey: XYJPKUCILBDKBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 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：

  2,3,5-tri-O-benzoyl-β-D-ribofuranosyl bromide 、 2,2,4-trimethyl-7-nitro-2,3-dihydro-1H-benzo[b][1,4]diazepine 反应 5.0h， 以82%的产率得到(2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(2,2,4-trimethyl-7-nitro-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：

  4-硝基邻苯二胺 、 丙酮 反应 3.5h， 以86%的产率得到2,2,4-trimethyl-7-nitro-2,3-dihydro-1H-benzo[b][1,4]diazepine
  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：

文献信息

• 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 2,3-Dihydro-1H-benzo[b][1,4]diazepines with Aromatic Diamines and Acetonedicarboxylic Acid
  作者：Juhyun Song

  DOI：10.14233/ajchem.2014.16301

  日期：——

  2,3-Dihydro-1H-benzo[b][1,4]diazepines were obtained by the reaction of the corresponding diamines and acetonedicarboxylic acid in various methods. A plausible mechanism for the formation of 1,5-benzodiazepine is also discussed.

  2,3- 二氢-1H-苯并[b][1,4]二氮杂卓是由相应的二胺和丙酮二羧酸通过各种方法反应得到的。此外，还讨论了形成 1,5-苯并二氮杂卓的合理机制。
• Kaupp, Gerd; Pogodda, Uwe; Schmeyers, Jens, Chemische Berichte, 1994, vol. 127, # 11, p. 2249 - 2262
  作者：Kaupp, Gerd、Pogodda, Uwe、Schmeyers, Jens

  DOI：——

  日期：——
• 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.
• 1,5-Benzoheteroazepines through eco-friendly general condensation reactions
  作者：Monica Nardi、Annalisa Cozza、Loredana Maiuolo、Manuela Oliverio、Antonio Procopio

  DOI：10.1016/j.tetlet.2011.06.029

  日期：2011.9

  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.