N-(benzyloxycarbonyl)-D,L-o-fluorophenylglycine | 124441-53-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(benzyloxycarbonyl)-D,L-o-fluorophenylglycine
• 英文别名: N-(Z)-Benzyloxycarbonyl-2-fluorophenylglycine；2-(2-fluorophenyl)-2-(phenylmethoxycarbonylamino)acetic acid
• CAS: 124441-53-8
• 化学式: C₁₆H₁₄FNO₄
• 分子量: 303.29
• InChiKey: XCCSKLSUZZWAKG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(benzyloxycarbonyl)-D,L-o-fluorophenylglycine 在 palladium on activated charcoal 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 为溶剂， -78.0~-23.0 ℃ 、344.73 kPa 条件下， 反应 24.5h， 生成
  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：

  2-氟-DL-Α-苯基甘氨酸 、 氯甲酸苄酯 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 0.17h， 以94%的产率得到N-(benzyloxycarbonyl)-D,L-o-fluorophenylglycine
  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

文献信息

• JANUSZ, J. M.;GARDLIK, J. M.;YOUNG, P. A.;BURKES, R. V.;STOLL, S. J.;ESTE+, J. MED. CHEM., 33,(1990) N, C. 1052-1061
  作者：JANUSZ, J. M.、GARDLIK, J. M.、YOUNG, P. A.、BURKES, R. V.、STOLL, S. J.、ESTE+

  DOI：——

  日期：——
• High potency dipeptide sweeteners. 1. L-Aspartyl-D-phenylglycine esters
  作者：J. M. Janusz、J. M. Gardlik、P. A. Young、R. V. Burkes、S. J. Stoll、A. F. Estelle、C. M. Riley

  DOI：10.1021/jm00165a027

  日期：1990.3

  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.