(S)-2-amino-N-benzyl-3-(4-hydroxyphenyl)propanamide | 40829-21-8

• 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: (S)-2-amino-N-benzyl-3-(4-hydroxyphenyl)propanamide
• 英文别名: (2S)-2-amino-N-benzyl-3-(4-hydroxyphenyl)propanamide
• CAS: 40829-21-8
• 化学式: C₁₆H₁₈N₂O₂
• 分子量: 270.331
• InChiKey: ASSKQXILTCJPQD-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  75.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-2-amino-N-benzyl-3-(4-hydroxyphenyl)propanamide 在 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 生成
  参考文献：
  名称：

  Development of Potent Inhibitors of Botulinum Neurotoxin Type B

  摘要：

  Botulinum neurotoxins are the most potent toxins known to date. They are zinc-metalloproteases able to cleave selectively an essential component of neurotransmitter exocytosis, causing the syndrome of botulism characterized by a flaccid paralysis. There is a great interest in designing antagonists of the action of these toxins. One way is to inhibit their catalytic activity. In this study, we report the design of such inhibitors directed toward BoNT/B. A study of the S-1 subsite specificity, using several beta-amino thiols, has shown that this subsite prefers a p-carboxybenzyl moiety. The specificity of the S-1' and S-2' subsites was studied using two libraries of pseudotripeptides containing the S-1 synthon derived from the best beta-amino thiol tested. Finally, a selection of various non natural amino acids for the recognition of the "prime" domain led to the most potent inhibitor of BoNT/B described to date with a K-i value of 20 nM.

  DOI：

  10.1021/jm0300680
• 作为产物：
  描述：

  N-苄氧羰基-L-酪氨酸 在 氢溴酸 、 溶剂黄146 作用下， 生成 (S)-2-amino-N-benzyl-3-(4-hydroxyphenyl)propanamide
  参考文献：
  名称：

  来自大肠杆菌B的酪氨酰转移核糖核酸合成酶。酪氨酸和腺苷5'-三磷酸结合位点的分析。

  摘要：

  DOI：

  10.1021/jm00261a025

文献信息

• Pd-Catalysed oxidative carbonylation of α-amino amides to hydantoins under mild conditions
  作者：Aleksandr Voronov、Vinayak Botla、Luca Montanari、Carla Carfagna、Raffaella Mancuso、Bartolo Gabriele、Giovanni Maestri、Elena Motti、Nicola Della Ca

  DOI：10.1039/d1cc04154a

  日期：——

  The first example of palladium-catalysed oxidative carbonylation of unprotected α-amino amides to hydantoins is described here. The selective synthesis of the target compounds was achieved under mild conditions (1 atm of CO), without ligands and bases. The catalytic system overrode the common reaction pathway that usually leads instead to the formation of symmetrical ureas.

  这里描述了钯催化氧化羰基化未保护的 α-氨基酰胺为乙内酰脲的第一个例子。目标化合物的选择性合成是在温和条件下（1 atm CO）实现的，无需配体和碱。催化系统超越了通常导致形成对称尿素的常见反应途径。
• Protecting-Group-Free Amidation of Amino Acids using Lewis Acid Catalysts
  作者：Marco T. Sabatini、Valerija Karaluka、Rachel M. Lanigan、Lee T. Boulton、Matthew Badland、Tom D. Sheppard

  DOI：10.1002/chem.201800372

  日期：2018.5.11

  Amidation of unprotected amino acids has been investigated using a variety of ‘classical“ coupling reagents, stoichiometric or catalytic group(IV) metal salts, and boron Lewis acids. The scope of the reaction was explored through the attempted synthesis of amides derived from twenty natural, and several unnatural, amino acids, as well as a wide selection of primary and secondary amines. The study also

  已使用多种“经典”偶联剂，化学计量或催化基团（IV）金属盐和硼路易斯酸研究了未保护氨基酸的酰胺化。通过尝试合成衍生自二十种天然和几种非天然氨基酸以及广泛选择的伯胺和仲胺的酰胺，探索了反应的范围。该研究还研究了药用相关化合物的合成，以及这种直接酰胺化方法的可扩展性。最后，我们提供了对在这些反应中观察到的化学选择性的见解。
• Abderhalden; Nienburg, Fermentforschung, 1933, vol. 13, p. 573,594
  作者：Abderhalden、Nienburg

  DOI：——

  日期：——
• Ekou, Lynda; Ekou, Tchirioua; Opalinski, Isabelle, E-Journal of Chemistry, 2011, vol. 8, # SUPPL. 1, p. S79-S84
  作者：Ekou, Lynda、Ekou, Tchirioua、Opalinski, Isabelle、Gesson, Jean Pierre

  DOI：——

  日期：——