2-(benzylamido)-3'-biphenylcarboxylic acid | 177171-14-1

• 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: 2-(benzylamido)-3'-biphenylcarboxylic acid
• 英文别名: 3-[2-[(2-Phenylacetyl)amino]phenyl]benzoic acid
• CAS: 177171-14-1
• 化学式: C₂₁H₁₇NO₃
• 分子量: 331.371
• InChiKey: RONVEXGILGCWGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  苄胺 、 2-(benzylamido)-3'-biphenylcarboxylic acid 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以96%的产率得到N-benzyl-2-(benzylamido)-3'-biphenylamide
  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：

  3-溴苯甲酰氯 在 盐酸 、 lithium hydroxide 、 sodium hydroxide 、 四(三苯基膦)钯 、 氯化亚砜 、 硼酸三甲酯 、 叠氮磷酸二苯酯 、 仲丁基锂 、 sodium carbonate 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 三乙胺 、 N,N-二异丙基乙胺 、 苯酚 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 315.67h， 生成 2-(benzylamido)-3'-biphenylcarboxylic 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

• 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.