N-tert-butyl-2-methyl-2-(7-methyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)propanamide | 1173204-00-6

• 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-methyl-2-(7-methyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)propanamide
• 英文别名: N-tert-butyl-2-methyl-2-(7-methyl-2,4-dioxo-1,5-dihydro-1,5-benzodiazepin-3-yl)propanamide
• CAS: 1173204-00-6
• 化学式: C₁₈H₂₅N₃O₃
• 分子量: 331.415
• InChiKey: NYKOIQOGCUPCBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 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 、 tert-butyl isocyanide 、 3,4-二氨基甲苯 在 iron(III) oxide 作用下， 以 二氯甲烷 为溶剂， 反应 2.2h， 以97%的产率得到N-tert-butyl-2-methyl-2-(7-methyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-yl)propanamide
  参考文献：
  名称：

  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

  摘要：

  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。

  DOI：

  10.1007/s11164-014-1915-z

文献信息

• 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.
• 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。