trifluoroaacetyl-β-L-aspartyl-p-cyanoanilide | 77658-85-6

• 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: trifluoroaacetyl-β-L-aspartyl-p-cyanoanilide
• 英文别名: L-Asparagine, N-(4-cyanophenyl)-N2-(trifluoroacetyl)-；(2S)-4-(4-cyanoanilino)-4-oxo-2-[(2,2,2-trifluoroacetyl)amino]butanoic acid
• CAS: 77658-85-6
• 化学式: C₁₃H₁₀F₃N₃O₄
• 分子量: 329.235
• InChiKey: SZNYTDISHYXTID-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.02
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  119.29
• 氢给体数：
  3.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  (S)-(-)-2-(三氟乙酰胺)琥珀酸酐 、 对氨基苯腈 以 四氢呋喃 为溶剂， 以35%的产率得到trifluoroaacetyl-α-L-aspartyl-p-cyanoanilide
  参考文献：
  名称：

  Peptide sweeteners. 5. Side chain homologs relating zwitterionic and trifluoroacetylated amino acid anilide and dipeptide sweeteners

  摘要：

  Side-chain homologues of sweet trifluoroacetyl-alpha-L-aspartyl-p-cyanoanilide have been synthesized and tasted. Removal of the trifluoroacetyl group only changes the potency of sweet taste, not the taste property. These results have been compared with the structure-taste relationships of dipeptide sweeteners. An informative discontinuity of taste effects was found to exist with novel aminomalonyl dipeptide derivatives. The results are explained on topochemical grounds.

  DOI：

  10.1021/jm00346a013

文献信息

• Peptide sweeteners. 7. Taste relationships of trifluoroacetyl-L-aspartylanilides
  作者：Marc Rodriguez、Murray Goodman

  DOI：10.1021/jm00378a024

  日期：1984.12

  A series of analogues of trifluoroacetyl-alpha-L-aspartylanilides substituted at various positions on the aromatic ring was synthesized and tasted. The position of the substitution is essential for the nature of the taste response. The results clearly establish the close relationship between sweet and bitter taste for these compounds. Combined electronic and topochemical contributions are discussed.