3'-<2-ethyl>-2-biphenylpropionic acid | 177171-05-0

• 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: 3'-<2-ethyl>-2-biphenylpropionic acid
• 英文别名: 3'-(N-(tert-butyloxycarbonyl)-2-aminoethyl)-2-biphenylpropionic acid；3-[2-[3-[2-[(2-Methylpropan-2-yl)oxycarbonylamino]ethyl]phenyl]phenyl]propanoic acid
• CAS: 177171-05-0
• 化学式: C₂₂H₂₇NO₄
• 分子量: 369.461
• InChiKey: NEVFEXXTSJZVEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3'-<2-ethyl>-2-biphenylpropionic acid 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.5h， 生成 N-benzyl-3'-(2-aminoethyl)-2-biphenylpropanamide
  参考文献：
  名称：

  Synthesis and Hydrogen Bonding Capabilities of Biphenyl-Based Amino Acids Designed To Nucleate β-Sheet Structure

  摘要：

  The syntheses of 3'-(aminoethyl)-2-biphenylpropionic acid (1) and 2-amino-3'-biphenylcarboxylic acid (2) are described. These residues were designed to nucleate beta-sheet structure in aqueous solution when incorporated into small, amphiphilic peptides in place of the backbone of the i + 1 and i + 2 residues of the beta-turn. N-Benzyl-3'-(2-(benzylamido)ethyl)-2-biphenylpropamide (3) and N-benzyl-(2-benzylamido)-3'-biphenylamide (4) were synthesized and studied as model compounds to investigate the hydrogen-bonding capabilities of residues 1 and 2, respectively. The X-ray crystal structure of 3 indicates that a 13-membered intramolecular hydrogen-bonded ring is formed, while the remaining amide proton and carbonyl are involved in intermolecular hydrogen bonding. Infrared and variable-temperature NMR experiments indicate that, in solution (CH2Cl2), 3 exists as an equilibrium mixture of the 13- and the 15-membered intramolecularly hydrogen-bonded conformers with the 15-membered ring conformer being favored. Amide 4 was shown to exist in solution (CH2Cl2) as an equilibrium mixture of the 11-membered intramolecular hydrogen-bonded ring and a nonbonded conformation. No contribution from the 9-membered hydrogen-bonded ring conformation was observed. The X-ray crystal structure of 4 indicated the absence of intramolecular hydrogen bonding in the solid state.

  DOI：

  10.1021/jo952194k
• 作为产物：
  描述：

  邻溴肉桂酸 在 platinum(IV) oxide palladium diacetate 、 lithium hydroxide 、 Wilkinson's catalyst 、 四(三苯基膦)钯 、 正丁基锂 、 硼酸三甲酯 、 叠氮磷酸二苯酯 、 氢气 、 一氯化碘 、 sodium carbonate 、 potassium carbonate 、 对甲苯磺酸 、 三乙胺 、 三苯基膦 作用下， 以 四氯化碳 、 乙醇 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， -95.0~150.0 ℃ 、344.73 kPa 条件下， 反应 157.17h， 生成 3'-<2-ethyl>-2-biphenylpropionic acid
  参考文献：
  名称：

  Synthesis and Hydrogen Bonding Capabilities of Biphenyl-Based Amino Acids Designed To Nucleate β-Sheet Structure

  摘要：

  The syntheses of 3'-(aminoethyl)-2-biphenylpropionic acid (1) and 2-amino-3'-biphenylcarboxylic acid (2) are described. These residues were designed to nucleate beta-sheet structure in aqueous solution when incorporated into small, amphiphilic peptides in place of the backbone of the i + 1 and i + 2 residues of the beta-turn. N-Benzyl-3'-(2-(benzylamido)ethyl)-2-biphenylpropamide (3) and N-benzyl-(2-benzylamido)-3'-biphenylamide (4) were synthesized and studied as model compounds to investigate the hydrogen-bonding capabilities of residues 1 and 2, respectively. The X-ray crystal structure of 3 indicates that a 13-membered intramolecular hydrogen-bonded ring is formed, while the remaining amide proton and carbonyl are involved in intermolecular hydrogen bonding. Infrared and variable-temperature NMR experiments indicate that, in solution (CH2Cl2), 3 exists as an equilibrium mixture of the 13- and the 15-membered intramolecularly hydrogen-bonded conformers with the 15-membered ring conformer being favored. Amide 4 was shown to exist in solution (CH2Cl2) as an equilibrium mixture of the 11-membered intramolecular hydrogen-bonded ring and a nonbonded conformation. No contribution from the 9-membered hydrogen-bonded ring conformation was observed. The X-ray crystal structure of 4 indicated the absence of intramolecular hydrogen bonding in the solid state.

  DOI：

  10.1021/jo952194k

文献信息

• A 2,3‘-Substituted Biphenyl-Based Amino Acid Facilitates the Formation of a Monomeric β-Hairpin-like Structure in Aqueous Solution at Elevated Temperature
  作者：Carey L. Nesloney、Jeffery W. Kelly

  DOI：10.1021/ja952472x

  日期：1996.1.1

  β-hairpin folding. An NMR structural evaluation of heptapeptides incorporating 1 revealed the presence of a hydrophobic cluster involving an aromatic ring of 1 and a side chain of one of the flanking hydrophobic α-amino acids, even though the peptides lack sufficient length to adopt a β-sheet structure. The flanking α-amino acid residues in these peptides exhibit significantly slower amide proton/deuterium

  [3'-(2-氨基乙基)-2-联苯]丙酸 (1) 和 2-氨基-3'-联苯羧酸 (2) 作为 β-折叠成核剂的评价是通过将这些残基结合到水溶性肽中来完成的. 残基 1 旨在取代 β-转角的 i+1 和 i+2 残基的骨架，并通过氢键疏水簇反转多肽链方向以启动 β-发夹折叠。结合 1 的七肽的 NMR 结构评估显示存在一个疏水簇，包括 1 的芳香环和侧链疏水性 α-氨基酸之一的侧链，即使肽缺乏足够的长度以采用 β-折叠结构. 这些肽中的侧翼 α-氨基酸残基表现出明显较慢的酰胺质子/氘交换速率，表明它们在水溶液中是分子内氢键。在合适的十三肽中，氢键的疏水簇使β-发夹结构的形成成核...
• Synthesis and Hydrogen Bonding Capabilities of Biphenyl-Based Amino Acids Designed To Nucleate β-Sheet Structure
  作者：Carey L. Nesloney、Jeffery W. Kelly

  DOI：10.1021/jo952194k

  日期：1996.1.1

  The syntheses of 3'-(aminoethyl)-2-biphenylpropionic acid (1) and 2-amino-3'-biphenylcarboxylic acid (2) are described. These residues were designed to nucleate beta-sheet structure in aqueous solution when incorporated into small, amphiphilic peptides in place of the backbone of the i + 1 and i + 2 residues of the beta-turn. N-Benzyl-3'-(2-(benzylamido)ethyl)-2-biphenylpropamide (3) and N-benzyl-(2-benzylamido)-3'-biphenylamide (4) were synthesized and studied as model compounds to investigate the hydrogen-bonding capabilities of residues 1 and 2, respectively. The X-ray crystal structure of 3 indicates that a 13-membered intramolecular hydrogen-bonded ring is formed, while the remaining amide proton and carbonyl are involved in intermolecular hydrogen bonding. Infrared and variable-temperature NMR experiments indicate that, in solution (CH2Cl2), 3 exists as an equilibrium mixture of the 13- and the 15-membered intramolecularly hydrogen-bonded conformers with the 15-membered ring conformer being favored. Amide 4 was shown to exist in solution (CH2Cl2) as an equilibrium mixture of the 11-membered intramolecular hydrogen-bonded ring and a nonbonded conformation. No contribution from the 9-membered hydrogen-bonded ring conformation was observed. The X-ray crystal structure of 4 indicated the absence of intramolecular hydrogen bonding in the solid state.