(R)-benzyl 2-(tert-butoxycarbonylamino)-4-oxo-4-(phenylamino)butanoate | 207502-24-7

• 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: (R)-benzyl 2-(tert-butoxycarbonylamino)-4-oxo-4-(phenylamino)butanoate
• 英文别名: benzyl (2S)-4-anilino-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoate
• CAS: 207502-24-7
• 化学式: C₂₂H₂₆N₂O₅
• 分子量: 398.459
• InChiKey: UKKWFYPGAVQDEY-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-benzyl 2-(tert-butoxycarbonylamino)-4-oxo-4-(phenylamino)butanoate 在 吡啶 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 (S)-2-(2-Acetylsulfanylmethyl-3-phenyl-propionylamino)-N-phenyl-succinamic acid benzyl ester
  参考文献：
  名称：

  New orally active enkephalinase inhibitors: their synthesis, biological activity, and analgesic properties

  摘要：

  A series of (4S)-4-[(2S)-benzyl-3-mercaptopropionylamino]-4-(N-phenylcarbamoyl)-butyric acids has been identified as potent systemically active enkephalinase inhibitors. Structure-activity relationships (SAR) are discussed. Further chemical modification of the inhibitors was carried out in order to identify the inhibitors which are orally active in an animal model. Compounds of particular interest are the prodrug-like analogues, including 5b (ONO-9902). Their analgesic effects after oral administration were evaluated. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(97)10048-7
• 作为产物：
  描述：

  Boc-L-天冬氨酸 1-苄酯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 (R)-benzyl 2-(tert-butoxycarbonylamino)-4-oxo-4-(phenylamino)butanoate
  参考文献：
  名称：

  New orally active enkephalinase inhibitors: their synthesis, biological activity, and analgesic properties

  摘要：

  A series of (4S)-4-[(2S)-benzyl-3-mercaptopropionylamino]-4-(N-phenylcarbamoyl)-butyric acids has been identified as potent systemically active enkephalinase inhibitors. Structure-activity relationships (SAR) are discussed. Further chemical modification of the inhibitors was carried out in order to identify the inhibitors which are orally active in an animal model. Compounds of particular interest are the prodrug-like analogues, including 5b (ONO-9902). Their analgesic effects after oral administration were evaluated. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(97)10048-7

文献信息

• Both Amide-Bearing α- and β-Amino Acids from Natural Aspartic Acid Are Efficient Organocatalysts for Enantioselective Aldol Reactions
  作者：Gen-Fa Wen、Rui Zhang、Chao-Shan Da、Chu-Yu Zhang

  DOI：10.1055/a-1953-1656

  日期：2023.2

  of structurally similar α- and β-amino acids in an asymmetric aldol transformation. Interestingly, aspartic acid is not only an α-amino acid, but also a β-amino acid. Thus, by modifying one of the two acidic groups of aspartic acid, two sets of α- and β-amino acids, 14 amino acids in total, were prepared and used as organocatalysts. The two types of amino acid, interestingly, achieved similar high catalytic

  这项工作旨在比较和探索结构相似的α-和β-氨基酸在不对称醛醇转化中的不同催化效率。有趣的是，天冬氨酸不仅是一种α-氨基酸，也是一种β-氨基酸。因此，通过修饰天冬氨酸的两个酸性基团之一，制备了两组α-和β-氨基酸，总共14个氨基酸，并用作有机催化剂。有趣的是，这两种氨基酸在不同的最佳条件下在不对称醛醇转化中实现了相似的高催化效率。在某些情况下，理想的 β-氨基酸甚至比理想的 α-氨基酸实现了显着更高的对映选择性，尽管 α-氨基酸在这种不对称转化中被广泛证明是高效的有机催化剂。
• Thio FCMA Intermediates as Strong Acyl Donors: A General Solution to the Formation of Complex Amide Bonds
  作者：Yu Rao、Xuechen Li、Samuel J. Danishefsky

  DOI：10.1021/ja906005j

  日期：2009.9.16

  Novel methodology for the formation of amide bonds under neutral conditions is described. Evidence is presented that the active acyl donors are thio FCMA intermediates, generated from the reactions of thioacids with isonitriles.