methyl (2S)-2-(methylideneamino)propanoate

• 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: methyl (2S)-2-(methylideneamino)propanoate
• 化学式: C₅H₉NO₂
• 分子量: 115.132
• InChiKey: YDXFXFNYLAHZDC-BYPYZUCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl (2S)-2-(methylideneamino)propanoate 在 propylphosphonic anhydride 、 N,N-二异丙基乙胺 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 56.0h， 生成 (S)-methyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-N-(cyanomethyl)propanamido)propanoate
  参考文献：
  名称：

  New Family of Peptidomimetics Based on the Imidazole Motif

  摘要：

  Starting from amino acid esters, new peptidomimetics based on the imidazole scaffold were prepared. An efficient and rapid sequence consisting of two subsequent one-pot procedures was developed and applied to various aminoacids. As they provide more substitution patterns, these heterocyclic mimics are promising tools for structural and biological studies.

  DOI：

  10.1021/ol102118u
• 作为产物：
  描述：

  聚合甲醛 、 L-丙氨酸甲酯盐酸盐 在 T406石油添加剂 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 生成 methyl (2S)-2-(methylideneamino)propanoate
  参考文献：
  名称：

  New Family of Peptidomimetics Based on the Imidazole Motif

  摘要：

  Starting from amino acid esters, new peptidomimetics based on the imidazole scaffold were prepared. An efficient and rapid sequence consisting of two subsequent one-pot procedures was developed and applied to various aminoacids. As they provide more substitution patterns, these heterocyclic mimics are promising tools for structural and biological studies.

  DOI：

  10.1021/ol102118u

文献信息

• Supramolecular Compounds from Multiple Ugi Multicomponent Macrocyclizations:  Peptoid-based Cryptands, Cages, and Cryptophanes
  作者：Daniel G. Rivera、Ludger A. Wessjohann

  DOI：10.1021/ja060720r

  日期：2006.6.1

  The first 3-fold multicomponent macrocyclizations of trifunctional building blocks were developed to produce, in one pot, cryptands, cages, and cryptophanes with peptoid tethers carrying additional recognition motifs. The straightforward, efficient, and diversity-oriented fashion by which these complex macromulticycles are obtained is suitable for building combinatorial libraries of synthetic receptors with potential applicability in catalysis and supramolecular and coordination chemistry. The strategy also easily allows creation of asymmetric macromulticyclic cavities, with up to 20 new bonds formed in one pot.
• Synthesis of peptidomimetic-spirostane hybrids via Ugi reaction: a versatile approach for the formation of peptide–steroid conjugates
  作者：Daniel G. Rivera、Orlando Pando、Francisco Coll

  DOI：10.1016/j.tet.2006.06.050

  日期：2006.8

  A general approach towards the preparation of peptide-steroid conjugates has been addressed. Utilizing the Ugi reaction, five peptidomimetic-steroid hybrids were achieved in good to excellent yields from carboxy- and amino-spirostanes and mono-protected alpha-amino acids. Diverse synthetic routes, specially focused on the formation of secosteroids, were implemented to introduce Ugi-type functionalities at different positions of the steroidal nucleus. This versatile approach is suitable for the formation of stable conjugates of steroids with other biologically relevant molecules. (c) 2006 Elsevier Ltd. All rights reserved.
• New Family of Peptidomimetics Based on the Imidazole Motif
  作者：Sylvain Petit、Corinne Fruit、Laurent Bischoff

  DOI：10.1021/ol102118u

  日期：2010.11.5

  Starting from amino acid esters, new peptidomimetics based on the imidazole scaffold were prepared. An efficient and rapid sequence consisting of two subsequent one-pot procedures was developed and applied to various aminoacids. As they provide more substitution patterns, these heterocyclic mimics are promising tools for structural and biological studies.