N-acetyldehydrophenylalanyl-S-proline | 35446-34-5

• 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-acetyldehydrophenylalanyl-S-proline
• 英文别名: N-Ac-Δ-Phe-Pro；N-Ac-ΔPhe-S-Pro；N-(α-Acetylaminocinnamoyl)-prolin；1-(α-acetylamino-ξ-cinnamoyl)-L-proline；1-(α-Acetylamino-ξ-cinnamoyl)-L-prolin；(2S)-1-(2-acetamido-3-phenylprop-2-enoyl)pyrrolidine-2-carboxylic acid
• CAS: 35446-34-5
• 化学式: C₁₆H₁₈N₂O₄
• 分子量: 302.33
• InChiKey: XTBSKDXUPYJHPU-AWEZNQCLSA-N

物化性质

• 沸点：
  649.1±55.0 °C(Predicted)
• 密度：
  1.309±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  86.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-acetyldehydrophenylalanyl-S-proline 在 氯化亚砜 、 氢气 、 calcium chloride 作用下， 以 乙醇 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Reaction of N-acetyldehydrophenylalanyl-S-proline with Ca(II) and Ni(II) ions and its role in asymmetric hydrogenation

  摘要：

  N-Ac-DELTAPhe-S-Pro forms strong coordination complexes with the CO2H group of the proline residue and weak coordination complexes through the -C(= O)-N groups with Ca(II) and Ni(II) ions in 95% aqueous methanol as indicated by the pK(a) values, PMR spectroscopy, and paramagnetic broadening of the C-13 NMR signals in the nickel complex. Complex formation enhances the rigidity of the dehydrodipeptide conformation, leading to a strong increase in the optical yield upon hydrogenation over achiral catalysts.

  DOI：

  10.1007/bf00864203
• 作为产物：
  描述：

  2-甲基-4-(苯基亚甲基)噁唑-5(4h)-酮 、 L-脯氨酸 生成 N-acetyldehydrophenylalanyl-S-proline
  参考文献：
  名称：

  Complexes of Ca2+ and Mg2+ withN-acetyl-α,β-dehydrodipeptides: the state in an alcoholic solution and its relationship with asymmetric induction upon diastereoselective hydrogenation

  摘要：

  In an alcoholic solution, N-acetyl-alpha,beta-dehydrodipeptides interact with Ca2+ and Mg2+ ions to form complex particles containing several dehydrodipeptide molecules per metal ion. The composition of these particles and steric interactions in them determine the acidity of the carboxyl groups and the degree of asymmetric induction upon diastereoselective hydrogenation.

  DOI：

  10.1007/bf02494633

文献信息

• Behrens; Doherty; Bergmann, Journal of Biological Chemistry, 1940, vol. 136, p. 61,64
  作者：Behrens、Doherty、Bergmann

  DOI：——

  日期：——
• Asymmetric hydrogenation ofN-acetyldehydrodipeptide complexes with Mg(II) and Ca(II) ions
  作者：I. N. Lisichkina、A. I. Vinogradova、N. B. Sukhorukova、E. V. Tselyapina、M. B. Saporovskaya、V. M. Belikov

  DOI：10.1007/bf00698456

  日期：1993.3

  N-Ac-DELTA-Phe-AA form labile complexes with Mg(II) ions. Potentiometric titration data show that the carboxyl group of the dehydrodipeptide in them scarcely participates in complexation, unlike the complexes with Ca(II) ions, The hydrogenation of these complexes over Pd/C occurs asymmetrically, the diastereomeric excess being as high as 58%.
• Diastereoselective hydrogenation of N-acetyldehydrodipeptides
  作者：V. K. Latov、A. I. Vinogradova、M. B. Saporovskaya、V. M. Belikov

  DOI：10.1007/bf00949793

  日期：1982.3