N-CBZ-β-benzyl-L-aspartyl-D-alanine α-(R,S)-cyclopropylbenzylamide | 165055-07-2

• 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: N-CBZ-β-benzyl-L-aspartyl-D-alanine α-(R,S)-cyclopropylbenzylamide
• CAS: 165055-07-2
• 化学式: C₃₂H₃₅N₃O₆
• 分子量: 557.646
• InChiKey: CXATZKPAGMOIBN-RKDLXEGRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.19
• 重原子数：
  41.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  122.83
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N-CBZ-β-benzyl-L-aspartyl-D-alanine α-(R,S)-cyclopropylbenzylamide 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 以93%的产率得到L-aspartyl-D-alanine (R,S)-α-cyclopropylbenzylamide
  参考文献：
  名称：

  Discovery and Synthesis of a New Series of High-Potency L-Aspartyl-D-.alpha.-aminoalkanoyl-(S)-.alpha.-alkylbenzylamide Sweeteners

  摘要：

  A new series of L-aspartyl-D-amino acid amide sweeteners is described in which the amide portion is prepared from an cl-alkyl-substituted benzylamine. These materials show good taste characteristics and are 5 times more stable than aspartame at typical beverage pH (3-4). The most potent member of the series is L-aspartyl-D-alpha-aminobutyric acid (S)-alpha-ethylbenzylamide, having a sweetness potency 2000 times that of a 10% sucrose solution.

  DOI：

  10.1021/jf00056a003
• 作为产物：
  描述：

  (3S)-4-[(2,5-二氧代-1-吡咯烷基)氧基]-4-氧代-3-[[(苯基甲氧基)羰基]氨基]-丁酸苄酯 在 N-羟基-5-降冰片烯-2,3-二甲酰亚胺 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 N-CBZ-β-benzyl-L-aspartyl-D-alanine α-(R,S)-cyclopropylbenzylamide
  参考文献：
  名称：

  Discovery and Synthesis of a New Series of High-Potency L-Aspartyl-D-.alpha.-aminoalkanoyl-(S)-.alpha.-alkylbenzylamide Sweeteners

  摘要：

  A new series of L-aspartyl-D-amino acid amide sweeteners is described in which the amide portion is prepared from an cl-alkyl-substituted benzylamine. These materials show good taste characteristics and are 5 times more stable than aspartame at typical beverage pH (3-4). The most potent member of the series is L-aspartyl-D-alpha-aminobutyric acid (S)-alpha-ethylbenzylamide, having a sweetness potency 2000 times that of a 10% sucrose solution.

  DOI：

  10.1021/jf00056a003