N-benzoyl-Δ-valyl-L-phenylalanine | 100803-82-5

• 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: N-benzoyl-Δ-valyl-L-phenylalanine
• 英文别名: (2S)-2-[(2-benzamido-3-methylbut-2-enoyl)amino]-3-phenylpropanoic acid
• CAS: 100803-82-5
• 化学式: C₂₁H₂₂N₂O₄
• 分子量: 366.417
• InChiKey: OCLPLEFZHZVIIQ-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  95.5
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-benzoyl-Δ-valyl-L-phenylalanine 在 palladium on activated charcoal 氢气 、 sodium methylate 、 magnesium chloride 作用下， 反应 96.0h， 生成 N-benzoyl-valyl-S-phenylalanine
  参考文献：
  名称：

  Diastereoselective hydrogenation of α,β-dehydrodipeptides bearing unsaturatedN-terminal amino acids and of ther complexes with CaCl2 and MgCl2

  摘要：

  The formation of complexes of dehydrodipeptides bearing N-terminal N-benzoyl-O-methyl-alpha,beta-dehydrotyrosine or N-benzoyl-alpha,beta-dehydrovaline residues with Ca2+ and Mg2+ ions enhances the diastereoselectivity of their hydrogenation; de of 66% and 80% were achieved. This method of increasing the stereoselectivity of hydrogenation is applicable to various dehydroamino acids at both the C- and N-termini of dehydrodipeptides.

  DOI：

  10.1007/bf02494374
• 作为产物：
  描述：

  2-phenyl-4-isopropylidene-5(4H)oxazolone 、 L-phenylalanine sodium salt 生成 N-benzoyl-Δ-valyl-L-phenylalanine
  参考文献：
  名称：

  Calderon, S.; Cativiela, C.; Mayoral, J. A., Bulletin des Societes Chimiques Belges, 1985, vol. 94, # 5, p. 435 - 438

  摘要：

  DOI：

文献信息

• Calderon, S.; Cativiela, C.; Mayoral, J. A., Bulletin des Societes Chimiques Belges, 1985, vol. 94, # 5, p. 435 - 438
  作者：Calderon, S.、Cativiela, C.、Mayoral, J. A.、Melendez, E.

  DOI：——

  日期：——
• Diastereoselective hydrogenation of α,β-dehydrodipeptides bearing unsaturatedN-terminal amino acids and of ther complexes with CaCl2 and MgCl2
  作者：I. N. Lisichkina、T. Yu. Vasil'eva、D. A. Davtyan、V. M. Belikov

  DOI：10.1007/bf02494374

  日期：1997.2

  The formation of complexes of dehydrodipeptides bearing N-terminal N-benzoyl-O-methyl-alpha,beta-dehydrotyrosine or N-benzoyl-alpha,beta-dehydrovaline residues with Ca2+ and Mg2+ ions enhances the diastereoselectivity of their hydrogenation; de of 66% and 80% were achieved. This method of increasing the stereoselectivity of hydrogenation is applicable to various dehydroamino acids at both the C- and N-termini of dehydrodipeptides.