D-phenylglycine (+/-)-endo-1,3,3-trimethyl-7-oxabicyclo<2.2.1>heptan-2-yl ester | 103251-87-2

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: D-phenylglycine (+/-)-endo-1,3,3-trimethyl-7-oxabicyclo<2.2.1>heptan-2-yl ester
• 英文别名: D-phenylglycine (+/-)-endo-1,3,3-trimethyl-7-oxabicyclo[2.2.1]heptan-2-yl ester
• CAS: 103251-87-2；124510-49-2；124510-50-5；124510-51-6；124510-52-7
• 化学式: C₁₇H₂₃NO₃
• 分子量: 289.375
• InChiKey: FBYHMWYJIPOHED-URMCTSMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  61.55
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  D-phenylglycine (+/-)-endo-1,3,3-trimethyl-7-oxabicyclo<2.2.1>heptan-2-yl ester 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 24.0h， 生成 (3S)-3-amino-4-oxo-4-[[(1R)-2-oxo-1-phenyl-2-[[(1S,2R,4R)-1,3,3-trimethyl-7-oxabicyclo[2.2.1]heptan-2-yl]oxy]ethyl]amino]butanoic acid
  参考文献：
  名称：

  High potency dipeptide sweeteners. 1. L-Aspartyl-D-phenylglycine esters

  摘要：

  Twenty esters of L-aspartyl-D-phenylglycine, as well as two substituted analogues, an o-fluoro and a p-hydroxy-phenylglycine ester, were prepared. The L-aspartyl-D-phenylglycine (-)-alpha- and (+)-beta-fenchyl esters had the highest sweetness potency at 1200 and 3700 times that of sucrose, respectively. The high potency of these sweeteners is surprising as the phenyl group occupies a position previously believed to accommodate only much smaller groups.

  DOI：

  10.1021/jm00165a027
• 作为产物：
  描述：

  N-<(o-nitrophenyl)sulfenyl>-D-phenylglycine (+/-)-endo-1,3,3-trimethyl-7-oxabicyclo<2.2.1>heptan-2-yl ester 在 盐酸 作用下， 以 丙酮 为溶剂， 以63%的产率得到D-phenylglycine (+/-)-endo-1,3,3-trimethyl-7-oxabicyclo<2.2.1>heptan-2-yl ester
  参考文献：
  名称：

  High potency dipeptide sweeteners. 1. L-Aspartyl-D-phenylglycine esters

  摘要：

  Twenty esters of L-aspartyl-D-phenylglycine, as well as two substituted analogues, an o-fluoro and a p-hydroxy-phenylglycine ester, were prepared. The L-aspartyl-D-phenylglycine (-)-alpha- and (+)-beta-fenchyl esters had the highest sweetness potency at 1200 and 3700 times that of sucrose, respectively. The high potency of these sweeteners is surprising as the phenyl group occupies a position previously believed to accommodate only much smaller groups.

  DOI：

  10.1021/jm00165a027