3-[N-(benzyloxy)acetamido]propionic acid | 170455-80-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-[N-(benzyloxy)acetamido]propionic acid
• 英文别名: N-acetyl-N-benzyloxy-β-alanine；3-[Acetyl(phenylmethoxy)amino]propanoic acid
• CAS: 170455-80-8
• 化学式: C₁₂H₁₅NO₄
• 分子量: 237.255
• InChiKey: FBCMEINPCRRMEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-[N-(benzyloxy)acetamido]propionic acid 在 palladium on activated charcoal 氢气 、 1-羟基苯并三唑一水物 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 2.0h， 生成 N,N-di(N-hydroxy-N-acetyl-β-alanyl)lysine methyl ester
  参考文献：
  名称：

  Easy Synthesis of Unnatural Siderophores

  摘要：

  N-Acetyl-N-benzyloxy-beta-alanine was obtained by Michael addition of N-acetyl-N-benzyloxyamine on terbutylacrylate under solvent-free PTC conditions followed by elimination of the terbutyl group. Polyamines were acylated with N-acetyl-N-benzyloxy-beta-alanine. The prepared compounds exhibited a moderate activity against HIV protease.

  DOI：

  10.1080/00397919508011794
• 作为产物：
  描述：

  3-[acetyl(benzyloxy)amino]propanoic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以91%的产率得到3-[N-(benzyloxy)acetamido]propionic acid
  参考文献：
  名称：

  Easy Synthesis of Unnatural Siderophores

  摘要：

  N-Acetyl-N-benzyloxy-beta-alanine was obtained by Michael addition of N-acetyl-N-benzyloxyamine on terbutylacrylate under solvent-free PTC conditions followed by elimination of the terbutyl group. Polyamines were acylated with N-acetyl-N-benzyloxy-beta-alanine. The prepared compounds exhibited a moderate activity against HIV protease.

  DOI：

  10.1080/00397919508011794

文献信息

• Iron(III) Complexes with Hybrid-Type Artificial Siderophores Containing Catecholate and Hydroxamate Sites
  作者：Tomohiko Inomata、Suguru Endo、Hiroki Ido、Reon Mori、Yusuke Iwai、Tomohiro Ozawa、Hideki Masuda

  DOI：10.1021/acs.inorgchem.3c01786

  日期：2023.10.9

  potentiometrically, and electrochemically. The results were compared with those previously reported for iron complexes with non-hybridized siderophores containing either catecholate or hydroxamate groups, K3[FeIIILC3] and [FeIIILH3]. Both K2[FeIIILC2H1] and K[FeIIILC1H2] formed six-coordinate octahedral iron(III) complexes. Evaluation of the thermodynamic properties of the complexes in an aqueous solution

  两种混合型人工铁载体配体，同时含有儿茶酚和异羟肟酸基团作为铁捕获位点，双（2,3-二羟基苯甲酰胺丙基）单[2-丙基]氨基甲烷（ H 5 L C2H1 ）和单（2,3-二羟基苯甲酰胺-丙基） ）设计并合成了双[2-丙基]氨基甲烷（H 4 L C1H2） 。制备了铁 (III) 配合物 K 2 [ Fe III L C2H1 ] 和 K[ Fe III L C1H2 ]，并通过光谱、电位和电化学进行了表征。将结果与之前报道的含有儿茶酚或异羟肟酸基团、K 3 [ Fe III L C3 ] 和 [ Fe III L H3 ] 的非杂交铁载体的铁络合物的结果进行比较。K 2 [ Fe III L C2H1 ] 和 K[ Fe III L C1H2 ] 均形成六配位八面体铁(III)配合物。对水溶液中配合物热力学性质的评估表明，K 2 [ Fe III L C2H1 ] 和 K[ Fe III L C1H2
• Mixed catechol-hydroxamate and catechol-(o-hydroxy)phenacyl siderophores: synthesis and uptake studies with receptor-deficient Escherichia coli mutants
  作者：Rainer Schobert、Andreas Stangl、Kerstin Hannemann

  DOI：10.1016/j.tet.2007.12.004

  日期：2008.2

  Biscatechol-hydroxamate and catechol-bishydroxamate chelators of similar architecture were synthesized by a small set of acylation reactions, Michael additions, and domino Wittig alkenations and they were tested for siderophoric activity in various receptor-deficient mutants of Escherichia coli under iron starvation. Growth promotion occurred only in mutants featuring catecholate recognizing receptors. Simplified mimics of the natural siderophores parabactin and agrobactin, carrying an o-hydroxybenzamide instead of the 2-(o-hydroxyphenyl)oxazoline ligand, were prepared analogously. Unlike the originals these mimics are fully functional siderophores in E. coli. (C) 2007 Elsevier Ltd. All rights reserved.