methyl 2-acetamido-3-(3-(trifluoromethyl)phenyl)propanoate | 82317-76-8

• 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: methyl 2-acetamido-3-(3-(trifluoromethyl)phenyl)propanoate
• 英文别名: methyl (2R)-2-acetamido-3-[3-(trifluoromethyl)phenyl]propanoate
• CAS: 82317-76-8
• 化学式: C₁₃H₁₄F₃NO₃
• 分子量: 289.254
• InChiKey: RHQQJMPGODBBGP-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-acetamido-3-(3-(trifluoromethyl)phenyl)propanoate 在 盐酸 作用下， 反应 2.0h， 以95%的产率得到(R)-2-Amino-3-(3-trifluoromethyl-phenyl)-propionic acid; hydrochloride
  参考文献：
  名称：

  Synthesis and biological activity of some very hydrophobic superagonist analogs of luteinizing hormone-releasing hormone

  摘要：

  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).

  DOI：

  10.1021/jm00349a006
• 作为产物：
  描述：

  diethyl α-acetamido, α-(3-trifluoromethylbenzyl)malonate 在 sodium hydroxide 、 三氟化硼乙醚 作用下， 反应 1.0h， 生成 methyl 2-acetamido-3-(3-(trifluoromethyl)phenyl)propanoate
  参考文献：
  名称：

  Synthesis and biological activity of some very hydrophobic superagonist analogs of luteinizing hormone-releasing hormone

  摘要：

  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).

  DOI：

  10.1021/jm00349a006

文献信息

• Site- and Stereoselective Chemical Editing of Thiostrepton by Rh-Catalyzed Conjugate Arylation: New Analogues and Collateral Enantioselective Synthesis of Amino Acids
  作者：Hanna M. Key、Scott J. Miller

  DOI：10.1021/jacs.7b08775

  日期：2017.11.1

  potassium salts as applied in the case of thiostrepton leads to a nearly full reversal of the enantioselectivity of the reaction. As such, this study of site-selective catalysis in a complex molecular setting also delivered synergistic insights in the arena of enantioselective catalysis. In addition, these studies greatly expand the number of known thiostrepton analogues obtained by any method and reveal a

  通过复杂分子的催化剂控制、选择性功能化来合成复杂的生物活性分子是一种新兴的能力。我们描述了 Rh 催化的共轭芳基化在硫链丝菌素修饰中的应用，硫链丝菌素是一种复杂的分子，具有强效抗菌特性，已知的类似物很少。通过这种方法，我们实现了硫链丝菌肽中存在的一个亚末端脱氢丙氨酸残基 (Dha16) 的位点和立体选择性功能化。这种方法的广泛范围使得能够制备和分离 24 种新的硫链丝菌素类似物，其生物学测试表明，硫链丝菌素的抗菌活性可以耐受 Dha16 到一系列氨基酸的改变。对该 Rh 催化过程的进一步分析表明，钠盐或钾盐的使用对于实现高立体选择性至关重要。通过应用于从脱氢丙氨酸单体合成氨基酯和酰胺，进一步研究了催化剂体系，发现该过程在比先前报道的类似反应更温和的条件下以高达 93:7 的 er 发生。此外，在硫链丝菌肽的情况下添加相同的钠盐和钾盐导致反应的对映选择性几乎完全逆转。因此，这项复杂分子环境中
• 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).