(R,S)-3-Ethyl-4-hexyl-1,4-benzodiazepine-2,5-dione | 184287-33-0

• 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: (R,S)-3-Ethyl-4-hexyl-1,4-benzodiazepine-2,5-dione
• 英文别名: 1H-1,4-Benzodiazepine-2,5-dione, 3-ethyl-4-hexyl-3,4-dihydro-；3-ethyl-4-hexyl-1,3-dihydro-1,4-benzodiazepine-2,5-dione
• CAS: 184287-33-0
• 化学式: C₁₇H₂₄N₂O₂
• 分子量: 288.39
• InChiKey: FJCBQZVZZSQSQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(N-叔丁氧羰基氨基)苯甲酸 在 乙酰氯 作用下， 以 甲醇 为溶剂， 反应 35.0h， 生成 (R,S)-3-Ethyl-4-hexyl-1,4-benzodiazepine-2,5-dione
  参考文献：
  名称：

  Improved Procedure for the Solution Phase Preparation of 1,4-Benzodiazepine-2,5-dione Libraries via Armstrong's Convertible Isonitrile and the Ugi Reaction

  摘要：

  DOI：

  10.1021/jo980622r

文献信息

• A Remarkable Two-Step Synthesis of Diverse 1,4-Benzodiazepine-2,5-diones Using the Ugi Four-Component Condensation
  作者：Thomas A. Keating、Robert W. Armstrong

  DOI：10.1021/jo961517p

  日期：1996.1.1

  A two-step, general synthesis of 1,4-benzodiazepine-2,5-diones (BZDs) is presented. This synthesis employs an Ugi four-component condensation using a convertible isocyanide (1-isocyanocyclohexene), followed by an acid-activated cyclization reaction. This synthesis represents a dramatically improved route to BZDs over those currently in the literature. In addition, since amino acids are not used as

  提出了两步的1,4-苯并二氮杂-2,5-二酮（BZDs）的一般合成。该合成采用可转化的异氰化物（1-异氰基环己烯）进行的Ugi四组分缩合，然后进行酸活化的环化反应。与目前文献中的那些相比，这种合成代表了向BZDs显着改善的途径。另外，由于不使用氨基酸作为输入，因此分子多样性的潜力远大于现有合成方法。还发现在室温下，在C-3和N-4位置被亚甲基取代的BZD在NMR光谱中显示构象异构现象。可变温度NMR实验支持这一观察结果，并得出有趣的结论，即在某些示例中，BZD核心结构可能不像以前想象的那样刚性。
• Novel safety-catch linker and its application with a Ugi/De-BOC/Cyclization (UDC) strategy to access carboxylic acids, 1,4-benzodiazepines, diketopiperazines, ketopiperazines and dihydroquinoxalinones
  作者：Christopher Hulme、John Peng、George Morton、Joseph M. Salvino、Tim Herpin、Richard Labaudiniere

  DOI：10.1016/s0040-4039(98)01593-7

  日期：1998.10

  This communication reveals the synthesis and application of a novel resin bound isonitrile. The resin is an example of a novel safety-catch linker which upon BOG-activation can be resin cleaved with a variety of nucleophiles. Use of this polymer supported isonitrile in the Ugi multi-component reaction (MCR), followed by resin clipping and cyclization allows access to diverse arrays of 1,4-benzodiazepine-2,5-diones, diketopiperazines and ketopiperazines respectively. The methoxide safety-catch clipping strategy and subsequent solution phase cyclization offers similar advantages to a traceless linker. (C) 1998 Elsevier Science Ltd. All rights reserved.