N-tert-butyl-2-(2,3,4,5-tetrahydro-2,4-dioxo-1H-benzo[b][1,4]diazepin-3-yl)-2-methyl propanamide | 1173203-95-6

• 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: N-tert-butyl-2-(2,3,4,5-tetrahydro-2,4-dioxo-1H-benzo[b][1,4]diazepin-3-yl)-2-methyl propanamide
• 英文别名: N-tert-butyl-2-(2,4-dioxo-1,5-dihydro-1,5-benzodiazepin-3-yl)-2-methylpropanamide
• CAS: 1173203-95-6
• 化学式: C₁₇H₂₃N₃O₃
• 分子量: 317.388
• InChiKey: MZKJYIGPVBWGSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  87.3
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  丙二酸环(亚)异丙酯 、 异氰酸叔丁酯 、 邻苯二胺 在 PrNH₂-surface-bound CoFe₂O₄ nanoparticles coated with SiO₂ 作用下， 以 二氯甲烷 为溶剂， 反应 1.67h， 以92%的产率得到N-tert-butyl-2-(2,3,4,5-tetrahydro-2,4-dioxo-1H-benzo[b][1,4]diazepin-3-yl)-2-methyl propanamide
  参考文献：
  名称：

  Synthesis of benzodiazepines catalyzed by CoFe₂O₄@SiO₂-PrNH₂ nanoparticles as a reusable catalyst

  摘要：

  CoFe₂O₄@SiO₂-PrNH₂纳米颗粒已被用作1,2-苯二胺、二甲酮、不同醛类或梅尔德鲁姆酸和异氰酸的多组分反应制备苯二氮䓬类化合物的高效催化剂。该方法具有多种优点，包括温和的反应条件、适用于广泛的底物、催化剂的可重复使用性和低催化剂负载量。

  DOI：

  10.1515/znb-2017-0023

文献信息

• Facile and efficient synthesis of benzo[b][1,5]diazepines by three-component coupling of aromatic diamines, Meldrum’s acid, and isocyanides catalyzed by Fe3O4 nanoparticles
  作者：Mohammad Ali Ghasemzadeh、Nasim Ghasemi-Seresht

  DOI：10.1007/s11164-014-1915-z

  日期：2015.11

  Highly effective one-pot synthesis of benzo[b][1,5]diazepines has been achieved by three-component (or, in situ, including catalyst and solvent, five-component) reaction of aromatic diamines, Meldrum’s acid, and isocyanides catalyzed by magnetite (Fe3O4) nanoparticles. Pharmaceutically and biologically active heterocyclic compounds including benzodiazepine derivatives were efficiently synthesized in excellent yields and short reaction times at room temperature. The significant features of the Fe3O4 nanoparticles are: easy preparation, cost-effectiveness, high stability, easy separation, low loading, and reusability of the catalyst. The heterogeneous nanoparticles were fully characterized by XRD, EDX, BET, SEM, TEM, and FT-IR analysis.

  通过芳香二胺、梅尔德伦酸和异氰酸酯的三组分（或原位，包括催化剂和溶剂的五组分）反应，催化剂为磁铁矿（Fe3O4）纳米颗粒，高效实现了一锅法合成苯并[b][1,5]二氮杂烯。具有药用和生物活性的杂环化合物，包括苯二氮杂衍生物，在室温下以优良的产率和短反应时间被有效合成。Fe3O4纳米颗粒的显著特性包括：制备简单、成本有效、高稳定性、易分离、低负载及催化剂的可重复使用。对这些异质纳米颗粒进行了XRD、EDX、BET、SEM、TEM和FT-IR分析的全面表征。
• Synthesis of benzodiazepines catalyzed by CoFe₂O₄@SiO₂-PrNH₂ nanoparticles as a reusable catalyst
  作者：Naiereh Sadat Miri、Javad Safaei-Ghomi

  DOI：10.1515/znb-2017-0023

  日期：2017.6.27

  CoFe₂O₄@SiO₂-PrNH₂ nanoparticles have been used as an efficient catalyst for the preparation of benzodiazepines by multi-component reactions of 1,2-phenylenediamine, dimedone, different aldehydes or Meldrum’s acid and isocyanides. This method provides several advantages including mild reaction conditions, the applicability to a wide range of substrates, the reusability of the catalyst and low catalyst loading.

  CoFe₂O₄@SiO₂-PrNH₂纳米颗粒已被用作1,2-苯二胺、二甲酮、不同醛类或梅尔德鲁姆酸和异氰酸的多组分反应制备苯二氮䓬类化合物的高效催化剂。该方法具有多种优点，包括温和的反应条件、适用于广泛的底物、催化剂的可重复使用性和低催化剂负载量。
• A Novel One-Pot Three-(<i>in Situ</i> Five-)Component Condensation Reaction: An Unexpected Approach for the Synthesis of Tetrahydro-2,4-dioxo-1<i>H</i>-benzo[<i>b</i>][1,5]diazepine-3-yl-2-methylpropanamide Derivatives
  作者：Ahmad Shaabani、Ali Hossein Rezayan、Sajjad Keshipour、Afshin Sarvary、Seik Weng Ng

  DOI：10.1021/ol901196z

  日期：2009.8.6

  A novel and efficient method has been developed for the synthesis of tetrahydro-2,4-dioxo-1H-benzo[b][1,5]diazepine-3-yl-2-methylpropanamide derivatives using an aromatic diamine, Meldrum's acid, and an isocyanide in CH2Cl2 at ambient temperature in high yields without using any catalyst or activation. The procedure provides an alternative method for the synthesis of benzo[b][1,5]diazepine derivatives. These compounds have closely related ring systems such as triflubazam, clobazam, and 1,5-benzodiazepines, which have a broad spectrum of biological activities.
• Synthesis of benzodiazepines catalyzed by chitosan functionalized by triacid imide as a superior catalyst
  作者：Mozhgan Esfandiari、Ali Kareem Abbas、Mohammad Reza Vakili、Hossein Shahbazi-Alavi、Javad Safaei-Ghomi

  DOI：10.1007/s11164-020-04281-x

  日期：2021.2

  Chitosan functionalized by triacid imide has been applied as an effective catalyst for the synthesis of benzodiazepines by one-pot reactions of 1,2-phenylenediamine with dimedone and aryl aldehydes or isocyanides and Meldrum’s acid. Chitosan functionalized by triacid imide was confirmed by FT-IR (infrared spectroscopy), XRD (X-ray diffraction), DSC (differential scanning calorimetry) and TGA (thermogravimetric analysis). To investigate the scope and limitation of this reaction, different aryl aldehydes and isocyanides were used as substrates. Good yields in short reaction times, experimental simplicity, extensive range of products, retrieval of the catalyst and low catalyst loading are some of the substantial aspects of this method.

  功能化三酸酰亚胺的壳聚糖被应用于通过一次性反应合成苯二氮杂烯类化合物，该反应涉及1,2-苯二胺与二甲酮、芳香醛或异氰酸酯及梅尔德鲁姆酸的反应。通过FT-IR（红外光谱）、XRD（X射线衍射）、DSC（差示扫描量热法）和TGA（热重分析）确认了功能化三酸酰亚胺的壳聚糖。为了研究该反应的范围和局限性，使用了不同的芳香醛和异氰酸酯作为底物。该方法的几个重要特点包括短反应时间内得到良好的产率、实验简便、产品范围广泛、催化剂可回收及低催化剂用量。