{2-[2'-(2-Benzylcarbamoyl-ethyl)-biphenyl-3-yl]-ethyl}-carbamic acid tert-butyl ester | 177171-06-1

• 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-[2'-(2-Benzylcarbamoyl-ethyl)-biphenyl-3-yl]-ethyl}-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[2-[3-[2-[3-(benzylamino)-3-oxopropyl]phenyl]phenyl]ethyl]carbamate
• CAS: 177171-06-1
• 化学式: C₂₉H₃₄N₂O₃
• 分子量: 458.601
• InChiKey: VBTUTSGSVVEWEC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  67.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  {2-[2'-(2-Benzylcarbamoyl-ethyl)-biphenyl-3-yl]-ethyl}-carbamic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 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 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 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 197.17h， 生成 {2-[2'-(2-Benzylcarbamoyl-ethyl)-biphenyl-3-yl]-ethyl}-carbamic acid tert-butyl ester
  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.