N-<(o-nitrophenyl)sulfenyl>-D-phenylglycine | 16679-41-7

• 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-<(o-nitrophenyl)sulfenyl>-D-phenylglycine
• 英文别名: (2R)-2-[(2-nitrophenyl)sulfanylamino]-2-phenylacetic acid
• CAS: 16679-41-7
• 化学式: C₁₄H₁₂N₂O₄S
• 分子量: 304.326
• InChiKey: ZTHYHACCPPSFOL-CYBMUJFWSA-N

物化性质

• 沸点：
  503.8±60.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.02
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  92.47
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-<(o-nitrophenyl)sulfenyl>-D-phenylglycine 在 palladium on activated charcoal 盐酸 、 4-二甲氨基吡啶 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 丙酮 为溶剂， -78.0~-23.0 ℃ 、344.73 kPa 条件下， 反应 24.5h， 生成 (3S)-3-amino-4-(((1R)-2-((2,5-dimethylcyclopentyl)oxy)-2-oxo-1-phenylethyl)amino)-4-oxobutanoic 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：

  左旋苯甘氨酸 、 2-硝基苯硫氯 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以62%的产率得到N-<(o-nitrophenyl)sulfenyl>-D-phenylglycine
  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