3-benzyl-1-butyl-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione | 1013314-36-7

• 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: 3-benzyl-1-butyl-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione
• 英文别名: (S)-3-benzyl-1-butyl-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione；(3S)-3-benzyl-1-butyl-3,4-dihydro-1,4-benzodiazepine-2,5-dione
• CAS: 1013314-36-7
• 化学式: C₂₀H₂₂N₂O₂
• 分子量: 322.407
• InChiKey: XQZLCAHTPXINJY-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 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：

  邻碘苯甲酰氯 在 titanium(IV) isopropylate 、 2-噻吩甲酸 、 copper(l) iodide 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 二甲基亚砜 、 甲苯 为溶剂， 反应 20.0h， 生成 3-benzyl-1-butyl-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione
  参考文献：
  名称：

  One-pot sequential Ti-/Cu-catalysis for tandem amidation/Ullmann-type cyclization: synthesis of model benzodiazepine(di)ones promoted by microwave irradiation

  摘要：

  微波辐照促进的序列Ti/Cu催化在苯二氮平（二）酮模型一锅合成中的应用，展示了双催化在适用于定向多样性合成的连接-环化方法中的便捷性。

  DOI：

  10.1039/c2ob07063d

文献信息

• The 1,4-Benzodiazepine-2,5-dione Small Molecule Template Results in Melanocortin Receptor Agonists with Nanomolar Potencies
  作者：Christine G. Joseph、Krista R. Wilson、Michael S. Wood、Nicholas B. Sorenson、Dong V. Phan、Zhimin Xiang、Rachel M. Witek、Carrie Haskell-Luevano

  DOI：10.1021/jm701303z

  日期：2008.3.13

  The melanocortin system consists of five seven-transmembrane spanning G-protein coupled receptors (MC1-5) that are stimulated by endogenous agonists and antagonized by the only two known endogenous antagonists of GPCRs, agouti and agouti-related protein (AGRP). These receptors have been associated with many physiological functions, including the involvement of the MC4R in feeding behavior and energy homeostasis, making this system an attractive target for the treatment of obesity. Small-molecule mimetics of endogenous ligands may result in the development of compounds with properties more suitable for use as therapeutic agents. The research presented herein involves the synthesis and analysis of 12 melanocortin receptor agonists using the 1,4-benzodiazepine-2,5-dione template and is the first report of these derivatives as melanocortin receptor agonists. Structure-activity relationship studies using this privileged structure, template has resulted in molecules with molecular weights around 400 that possess nanomolar agonist potency at the melanocortin receptors examined in this study.
• One-pot sequential Ti-/Cu-catalysis for tandem amidation/Ullmann-type cyclization: synthesis of model benzodiazepine(di)ones promoted by microwave irradiation
  作者：Leonardo Ciofi、Andrea Trabocchi、Claudia Lalli、Gloria Menchi、Antonio Guarna

  DOI：10.1039/c2ob07063d

  日期：——

  The application of sequential Ti-/Cu-catalysis in the model one-pot synthesis of benzodiazepine(di)ones promoted by microwave irradiation demonstrates the expediency of dual catalysis in coupling-cyclization methods useful for diversity-oriented synthesis.

  微波辐照促进的序列Ti/Cu催化在苯二氮平（二）酮模型一锅合成中的应用，展示了双催化在适用于定向多样性合成的连接-环化方法中的便捷性。