(S)-3-Benzyl-7-chloro-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione

• 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: (S)-3-Benzyl-7-chloro-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione
• 英文别名: (3S)-3-benzyl-7-chloro-3,4-dihydro-1H-1,4-benzodiazepine-2,5-dione
• 化学式: C₁₆H₁₃ClN₂O₂
• 分子量: 300.744
• InChiKey: OWJDCXCIRLYLKF-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  L-苯丙氨酸甲酯盐酸盐 、 2-氨基-5-氯苯甲酸 生成 (S)-3-Benzyl-7-chloro-3,4-dihydro-1H-benzo[e][1,4]diazepine-2,5-dione
  参考文献：
  名称：

  An expedient and high-yielding method for the solid-phase synthesis of diverse 1,4-benzodiazepine-2,5-diones

  摘要：

  DOI：

  10.1021/jo00123a001

文献信息

• An expedient and high-yielding method for the solid-phase synthesis of diverse 1,4-benzodiazepine-2,5-diones
  作者：Constantine G. Boojamra、Kristina M. Burow、Jonathan A. Ellman

  DOI：10.1021/jo00123a001

  日期：1995.9
• Solid-Phase Synthesis of 1,4-Benzodiazepine-2,5-diones. Library Preparation and Demonstration of Synthesis Generality
  作者：Constantine G. Boojamra、Kristina M. Burow、Lorin A. Thompson、Jonathan A. Ellman

  DOI：10.1021/jo9622845

  日期：1997.3.1

  A general and expedient method has been developed for the solid-phase synthesis of 1,4-benzodiazepine-2,5-diones 1 from three commercially available components; anthranilic acids, alpha-amino esters, and alkylating agents. Reaction conditions have been developed to prepare either racemic compounds for lead identification efforts or optically pure compounds for lead optimization efforts. The incorporation of diverse functionality into the benzodiazepine products has also been demonstrated. On the basis of the scope and generality of the synthesis sequence, a library of 1,4-benzodiazepine-2,5-diones has been prepared from 11 alkylating agents, 12 anthranilic acids, and 19 alpha-amino esters (nine sets of enantiomeric pairs and glycine methyl ester hydrochloride). The library was prepared in a spatially separate format using a microtiter-based apparatus that is inexpensive and straightforward to construct from ordinary items found in an organic or bioorganic laboratory. The high quality of the 1,4-benzodiazepine-2,5-dione library has been demonstrated by evaluating representative compounds by HPLC analysis and H-1 NMR.