N-乙酰基-DL-(3-三氟甲基)苯丙氨酸 | 82337-57-3

• 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
• 中文名称: N-乙酰基-DL-(3-三氟甲基)苯丙氨酸
• 英文名称: 2-Acetamino-3-<3-trifluormethyl-phenyl>-propionsaeure
• 英文别名: N-Acetyl-3-(trifluoromethyl)phenylalanine；2-acetamido-3-[3-(trifluoromethyl)phenyl]propanoic acid
• CAS: 82337-57-3
• 化学式: C₁₂H₁₂F₃NO₃
• mdl: MFCD07700207
• 分子量: 275.227
• InChiKey: SZKGWNHMAJBPFY-UHFFFAOYSA-N

物化性质

• 熔点：
  132-133 °C(Solv: acetone (67-64-1); water (7732-18-5))
• 沸点：
  435.6±45.0 °C(Predicted)
• 密度：
  1.334±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-乙酰基-DL-(3-三氟甲基)苯丙氨酸 生成 3-三氟甲基-DL-苯丙氨酸
  参考文献：
  名称：

  Fluorinated Aromatic Amino Acids. I. o-, m-, and p-Trifluoromethylphenylalanines¹

  摘要：

  DOI：

  10.1021/jo01075a015
• 作为产物：
  描述：

  2-Phenyl-4-<3-trifluormethyl-benzyliden>-oxazolon-(5) 在 palladium on activated charcoal 氢气 作用下， 生成 N-乙酰基-DL-(3-三氟甲基)苯丙氨酸
  参考文献：
  名称：

  Fluorinated Aromatic Amino Acids. I. o-, m-, and p-Trifluoromethylphenylalanines¹

  摘要：

  DOI：

  10.1021/jo01075a015

文献信息

• Synthesis and biological activity of some very hydrophobic superagonist analogs of luteinizing hormone-releasing hormone
  作者：John J. Nestor、Teresa L. Ho、Richard A. Simpson、Bonnie L. Horner、Gordon H. Jones、Georgia I. McRae、Brian H. Vickery

  DOI：10.1021/jm00349a006

  日期：1982.7

  The effect of increased hydrophobicity at position 6 of luteinizing hormone-releasing hormone (LH-RH) has been investigated by the incorporation of a series of 15 very hydrophobic, unnatural D-amino acids at this position. The unnatural amino acids studied can be considered analogues of phenylalanine with carbocyclic aromatic side chains consisting of substituted phenyl (e.g., 2,4,6-trimethylphenyl, p-biphenyl) or polycyclic aromatic (e.g., naphthalene, anthracene) units. When enzymatic resolution (subtilisin Carlsberg) of the most hydrophobic amino acids failed, the racemic amino acids were incorporated, and the diastereomeric LH-RH analogues were resolved by preparative high-performance liquid chromatography. The analogues were synthesized by the solid-phase technique. All of the synthetic compounds were very potent LH-RH superagonists, but [6-(3-(2-naphthyl)-D-alanine)]LH-RH, [6-(3-(2-naphthyl)-D-alanine), 7-(N alpha-methylleucine)]LH-RH and [6-(3-(2,4,6-trimethylphenyl)-D-alanine)]LH-RH appear to be among the most potent LH-RH agonist analogues yet reported when tested in a rat estrus cyclicity suppression assay designed to show the paradoxical antifertility effects of these compounds [ED50 approximately 7 x 10(-8) g; twice daily in saline]. These analogues are twice as potent as [D-Trp6,ProNHEt9]LH-RH in this assay system (i.e., approximately 200 times the potency of LH-RH).
• Fluorinated Aromatic Amino Acids. I. o-, m-, and p-Trifluoromethylphenylalanines¹
  作者：ROBERT FILLER、HERMAN NOVAR

  DOI：10.1021/jo01075a015

  日期：1960.5