N-(2-Azido-benzyl)-N-((S)-1-phenyl-ethyl)-acrylamide | 364802-09-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(2-Azido-benzyl)-N-((S)-1-phenyl-ethyl)-acrylamide
• 英文别名: N-[(2-azidophenyl)methyl]-N-[(1S)-1-phenylethyl]prop-2-enamide
• CAS: 364802-09-5
• 化学式: C₁₈H₁₈N₄O
• 分子量: 306.367
• InChiKey: OUMKBDHOBMYKIY-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  34.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(2-Azido-benzyl)-N-((S)-1-phenyl-ethyl)-acrylamide 在 三乙胺 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 1.75h， 生成 (S)-3-((S)-1-Phenyl-ethyl)-1,1a,3,4-tetrahydro-3,8b-diaza-benzo[a]cyclopropa[c]cyclohepten-2-one
  参考文献：
  名称：

  Stereoselective intramolecular cycloadditions of homochiral N-alkenoyl aryl azides

  摘要：

  Starting from the commercially available (S)-1-phenylethylamine and L-alanine benzylester, we synthesised the homochiral N-alkenoyl aryl azides 2a-2d. The intramolecular cycloaddition of unsubstituted 2a and ab gave enantiopure 3.3a-dihydro-1,2,3-triazolo[1.5-a][1.4]benzodiazepine-4(6H)-ones 3a, 3b, 4a and 4b, while phenyl-substituted 2c and 2d gave enantiopure 1.1a-dihydro-2H-azirino[2.1-c][1,4]benzodiazepine-4(6H)-ones 5c, 5d, 6c and 6d. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00190-2
• 作为产物：
  描述：

  N-[(2-aminophenyl)methyl]-N-[(1S)-1-phenylethyl]prop-2-enamide 在 盐酸 、 sodium nitrite 、 sodium azide 作用下， 以 溶剂黄146 、 乙醚 为溶剂， 反应 1.5h， 生成 N-(2-Azido-benzyl)-N-((S)-1-phenyl-ethyl)-acrylamide
  参考文献：
  名称：

  Stereoselective intramolecular cycloadditions of homochiral N-alkenoyl aryl azides

  摘要：

  Starting from the commercially available (S)-1-phenylethylamine and L-alanine benzylester, we synthesised the homochiral N-alkenoyl aryl azides 2a-2d. The intramolecular cycloaddition of unsubstituted 2a and ab gave enantiopure 3.3a-dihydro-1,2,3-triazolo[1.5-a][1.4]benzodiazepine-4(6H)-ones 3a, 3b, 4a and 4b, while phenyl-substituted 2c and 2d gave enantiopure 1.1a-dihydro-2H-azirino[2.1-c][1,4]benzodiazepine-4(6H)-ones 5c, 5d, 6c and 6d. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00190-2

文献信息

• A one-step synthesis of enantiopure 2-substituted 4,5-dihydro-1,4-benzodiazepine-3-ones via intramolecular azide cycloaddition
  作者：Giorgio Molteni、Paola Del Buttero

  DOI：10.1016/j.tetasy.2007.05.015

  日期：2007.6

  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.
• Stereoselective intramolecular cycloadditions of homochiral N-alkenoyl aryl azides
  作者：Gianluigi Broggini、Luisa Garanti、Giorgio Molteni、Tullio Pilati

  DOI：10.1016/s0957-4166(01)00190-2

  日期：2001.5

  Starting from the commercially available (S)-1-phenylethylamine and L-alanine benzylester, we synthesised the homochiral N-alkenoyl aryl azides 2a-2d. The intramolecular cycloaddition of unsubstituted 2a and ab gave enantiopure 3.3a-dihydro-1,2,3-triazolo[1.5-a][1.4]benzodiazepine-4(6H)-ones 3a, 3b, 4a and 4b, while phenyl-substituted 2c and 2d gave enantiopure 1.1a-dihydro-2H-azirino[2.1-c][1,4]benzodiazepine-4(6H)-ones 5c, 5d, 6c and 6d. (C) 2001 Elsevier Science Ltd. All rights reserved.