(E)-N-[(2-aminophenyl)methyl]-3-phenyl-N-[(1S)-1-phenylethyl]prop-2-enamide | 260352-58-7

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-N-[(2-aminophenyl)methyl]-3-phenyl-N-[(1S)-1-phenylethyl]prop-2-enamide
• CAS: 260352-58-7
• 化学式: C₂₄H₂₄N₂O
• 分子量: 356.467
• InChiKey: OSXRQQUXXWMAQB-PIOKWQJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  46.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-N-[(2-aminophenyl)methyl]-3-phenyl-N-[(1S)-1-phenylethyl]prop-2-enamide 在 盐酸 、 三乙胺 、 sodium nitrite 作用下， 以 溶剂黄146 、 甲苯 为溶剂， 反应 9.0h， 生成 (1R,1aS)-1-Phenyl-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：

  (E)-N-[(2-nitrophenyl)methyl]-3-phenyl-N-[(1S)-1-phenylethyl]prop-2-enamide 在 铁粉 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以95%的产率得到(E)-N-[(2-aminophenyl)methyl]-3-phenyl-N-[(1S)-1-phenylethyl]prop-2-enamide
  参考文献：
  名称：

  Asymmetric induction by the (S)-1-phenylethyl group in intramolecular nitrile imine cycloadditions giving enantiopure 3,3a-dihydro-pyrazolo[1,5-a][1,4]benzodiazepine-4(6H)-ones

  摘要：

  Stereoselective intramolecular cycloadditions of homochiral nitrile imines 5 are described as a fruitful source of enantiopure 3,3a-dihydro-pyrazolo[1,5-a][1,4]benzodiazepine-4(6H)-ones 6 and 7. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(99)00493-0

文献信息

• Asymmetric induction by the (S)-1-phenylethyl group in intramolecular nitrile imine cycloadditions giving enantiopure 3,3a-dihydro-pyrazolo[1,5-a][1,4]benzodiazepine-4(6H)-ones
  作者：Gianluigi Broggini、Gianluigi Casalone、Luisa Garanti、Giorgio Molteni、Tullio Pilati、Gaetano Zecchi

  DOI：10.1016/s0957-4166(99)00493-0

  日期：1999.11

  Stereoselective intramolecular cycloadditions of homochiral nitrile imines 5 are described as a fruitful source of enantiopure 3,3a-dihydro-pyrazolo[1,5-a][1,4]benzodiazepine-4(6H)-ones 6 and 7. (C) 1999 Elsevier Science 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.