(3S)-7-氯-3-[(4-羟基苯基)甲基]-5-苯基-1,3-二氢-1,4-苯并二氮杂-2-酮 | 50691-93-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 中文名称: (3S)-7-氯-3-[(4-羟基苯基)甲基]-5-苯基-1,3-二氢-1,4-苯并二氮杂-2-酮
• 英文名称: (S)-7-chloro-1,3-dihydro-3-p'-hydroxybenzyl-5-phenyl-2H-1,3-benzodiazepine-2-one
• 英文别名: 7-chloro-3-(4-hydroxy-benzyl)-5-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one；2H-1,4-Benzodiazepin-2-one, 1,3-dihydro-7-chloro-3-((4-hydroxyphenyl)methyl)-5-phenyl-, (S)-；(3S)-7-chloro-3-[(4-hydroxyphenyl)methyl]-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one
• CAS: 50691-93-5
• 化学式: C₂₂H₁₇ClN₂O₂
• 分子量: 376.842
• InChiKey: DWQPHVZCAFGJBO-FQEVSTJZSA-N

物化性质

• 沸点：
  595.9±50.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  61.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 10.0h， 生成 (3S)-7-氯-3-[(4-羟基苯基)甲基]-5-苯基-1,3-二氢-1,4-苯并二氮杂-2-酮
  参考文献：
  名称：

  Discrimination between Enantiomers of Structurally Related Molecules:  Separation of Benzodiazepines by Molecularly Imprinted Polymers

  摘要：

  Molecular imprinting has been used to create synthetic receptor sites for a series of chiral benzodiazepines. A detailed HPLC analysis of binding properties using molecularly imprinted polymers (MIPs) as the stationary phase showed that binding, as measured by chromatographic retention, shows significant dependence on the chiral match or mismatch. In addition, the shape and spatial orientation of functionality of the imprinted binding site is also critical for recognition. Imprinted polymers, therefore, are not only able to discriminate between enantiomers of the imprinted molecule, they also demonstrate an ability to discriminate between a wide range of enantiomers of structurally related molecules that have not been imprinted. The ability of MIPs to discriminate between enantiomers of molecules in favor of the imprinted absolute configuration, even as the structural homology between the enantiomers and the original template decreases, indicates that the synthetic benzodiazepine receptors may serve as crude mimics of the natural receptor.

  DOI：

  10.1021/ja9926313

文献信息

• Discrimination between Enantiomers of Structurally Related Molecules:  Separation of Benzodiazepines by Molecularly Imprinted Polymers
  作者：Bradley R. Hart、Daniel J. Rush、Kenneth J. Shea

  DOI：10.1021/ja9926313

  日期：2000.1.1

  Molecular imprinting has been used to create synthetic receptor sites for a series of chiral benzodiazepines. A detailed HPLC analysis of binding properties using molecularly imprinted polymers (MIPs) as the stationary phase showed that binding, as measured by chromatographic retention, shows significant dependence on the chiral match or mismatch. In addition, the shape and spatial orientation of functionality of the imprinted binding site is also critical for recognition. Imprinted polymers, therefore, are not only able to discriminate between enantiomers of the imprinted molecule, they also demonstrate an ability to discriminate between a wide range of enantiomers of structurally related molecules that have not been imprinted. The ability of MIPs to discriminate between enantiomers of molecules in favor of the imprinted absolute configuration, even as the structural homology between the enantiomers and the original template decreases, indicates that the synthetic benzodiazepine receptors may serve as crude mimics of the natural receptor.