2-{N-[1-(S)-(benzyloxycarbonyl)ethyl]-N-(1-oxo-2-(E)-butenyl)aminomethyl}phenylazide | 946533-89-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-{N-[1-(S)-(benzyloxycarbonyl)ethyl]-N-(1-oxo-2-(E)-butenyl)aminomethyl}phenylazide
• 英文别名: benzyl (2S)-2-[(2-azidophenyl)methyl-[(E)-but-2-enoyl]amino]propanoate
• CAS: 946533-89-7
• 化学式: C₂₁H₂₂N₄O₃
• 分子量: 378.431
• InChiKey: LFFGAXHSTRMLIE-CFZDNBDDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  61
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-{N-[1-(S)-(benzyloxycarbonyl)ethyl]-N-(1-oxo-2-(E)-butenyl)aminomethyl}phenylazide 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以96%的产率得到2-ethyl-4-[1-(S)-(benzyloxycarbonyl)ethyl]-4,5-dihydro-1,4-benzodiazepin-3-one
  参考文献：
  名称：

  A one-step synthesis of enantiopure 2-substituted 4,5-dihydro-1,4-benzodiazepine-3-ones via intramolecular azide cycloaddition

  摘要：

  Starting from the appropriate azides bearing the (S)-1-phenylethylamine and the L-alanine benzylester as chiral pendants, a facile and effective synthetic route to the title compounds in their enantiopure form was developed with excellent product yields obtained. Basic hydrolysis of the ester group of the title compounds 3a-c gave the corresponding, readily functionalisable carboxylic acids. Catalytic reduction of 2-benzyl derivatives 3c and 3f gave 4-functionalised 1,2,4,5-tetrahydro-1,4-benzodiazepin-3-ones in enantiopure forms. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.05.015
• 作为产物：
  描述：

  2-{N-[1-(S)-(benzyloxycarbonyl)ethyl]-N-(1-oxo-2-(E)-butenyl)aminomethyl}aniline 在 盐酸 、 溶剂黄146 、 sodium nitrite 、 sodium azide 作用下， 以 乙醚 为溶剂， 反应 1.5h， 以90%的产率得到2-{N-[1-(S)-(benzyloxycarbonyl)ethyl]-N-(1-oxo-2-(E)-butenyl)aminomethyl}phenylazide
  参考文献：
  名称：

  A one-step synthesis of enantiopure 2-substituted 4,5-dihydro-1,4-benzodiazepine-3-ones via intramolecular azide cycloaddition

  摘要：

  Starting from the appropriate azides bearing the (S)-1-phenylethylamine and the L-alanine benzylester as chiral pendants, a facile and effective synthetic route to the title compounds in their enantiopure form was developed with excellent product yields obtained. Basic hydrolysis of the ester group of the title compounds 3a-c gave the corresponding, readily functionalisable carboxylic acids. Catalytic reduction of 2-benzyl derivatives 3c and 3f gave 4-functionalised 1,2,4,5-tetrahydro-1,4-benzodiazepin-3-ones in enantiopure forms. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2007.05.015