N-benzyloxycarbonyl-D-alanine (+)-α-fenchyl ester | 108646-35-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: N-benzyloxycarbonyl-D-alanine (+)-α-fenchyl ester
• CAS: 108646-35-1
• 化学式: C₂₁H₂₉NO₄
• 分子量: 359.466
• InChiKey: VENOVJYXVBABRV-NHAHXKBOSA-N

物化性质

• 沸点：
  472.5±38.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.06
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  64.63
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  N-benzyloxycarbonyl-D-alanine (+)-α-fenchyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 D-alanine (+)-α-fenchyl ester
  参考文献：
  名称：

  Synthesis and Sweetness Characteristics of l-Aspartyl-d-Alanine Fenchyl Esters

  摘要：

  Four isomers of the L-aspartyl-D-alanine fenchyl esters were prepared as potential peptide sweeteners. L-Aspartyl-D-alanine (+)-alpha -fenchyl ester and L-aspartyl-D-alanine (-)-beta -fenchyl ester showed sweetness with potencies 250 and 160 times higher than that of sucrose, respectively. In contrast, L-aspartyl-D-alanine (+)-beta -fenchyl ester and L-:aspartyl-D-alanine (-)-alpha -fenchyl ester had the highest sweetness potencies at 5700 and 1100 times that of sucrose, respectively. In particular, L-aspartyl-D-alanine (-)-alpha -fenchyl ester had an excellent sweetness quality; but L-,aspartyl-D-alanine (+)-beta -fenchyl ester did not have an excellent quality of sweetness because it displayed an aftertaste caused by the strong sweetness.

  DOI：

  10.1021/jf010344o
• 作为产物：
  描述：

  (1R)-1,3,3-三甲基二环[2.2.1]庚-2-酮 在 4-二甲氨基吡啶 、 aluminum isopropoxide 、 N,N'-二环己基碳二亚胺 、 异丙醇 作用下， 以 二氯甲烷 为溶剂， 反应 426.5h， 生成 N-benzyloxycarbonyl-D-alanine (+)-α-fenchyl ester
  参考文献：
  名称：

  Synthesis and Sweetness Characteristics of l-Aspartyl-d-Alanine Fenchyl Esters

  摘要：

  Four isomers of the L-aspartyl-D-alanine fenchyl esters were prepared as potential peptide sweeteners. L-Aspartyl-D-alanine (+)-alpha -fenchyl ester and L-aspartyl-D-alanine (-)-beta -fenchyl ester showed sweetness with potencies 250 and 160 times higher than that of sucrose, respectively. In contrast, L-aspartyl-D-alanine (+)-beta -fenchyl ester and L-:aspartyl-D-alanine (-)-alpha -fenchyl ester had the highest sweetness potencies at 5700 and 1100 times that of sucrose, respectively. In particular, L-aspartyl-D-alanine (-)-alpha -fenchyl ester had an excellent sweetness quality; but L-,aspartyl-D-alanine (+)-beta -fenchyl ester did not have an excellent quality of sweetness because it displayed an aftertaste caused by the strong sweetness.

  DOI：

  10.1021/jf010344o