N-benzyloxy-N-(2-(benzyloxycarbonyl)ethyl) 3-bis(2'-hydroxyethyl)aminopropionamide | 1013313-69-3

• 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-benzyloxy-N-(2-(benzyloxycarbonyl)ethyl) 3-bis(2'-hydroxyethyl)aminopropionamide
• 英文别名: Benzyl 3-[3-[bis(2-hydroxyethyl)amino]propanoyl-phenylmethoxyamino]propanoate；benzyl 3-[3-[bis(2-hydroxyethyl)amino]propanoyl-phenylmethoxyamino]propanoate
• CAS: 1013313-69-3
• 化学式: C₂₄H₃₂N₂O₆
• 分子量: 444.528
• InChiKey: QIIJYWRBMSUJNS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  32
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  99.5
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-formylmethyl 2,3-dibenzyloxybenzamide 、 N-benzyloxy-N-(2-(benzyloxycarbonyl)ethyl) 3-bis(2'-hydroxyethyl)aminopropionamide 、 (三苯基膦烯)乙烯酮 在 苯甲酸 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 以55%的产率得到N-benzyloxy-N-(2-(benzyloxycarbonyl)ethyl) 3-di[8'-aza-3'-oxa-4',9'-dioxo-9'-(2'',3''-dibenzyloxyphenyl)non-5'-enyl]aminopropionamide
  参考文献：
  名称：

  Mixed catechol-hydroxamate and catechol-(o-hydroxy)phenacyl siderophores: synthesis and uptake studies with receptor-deficient Escherichia coli mutants

  摘要：

  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.

  DOI：

  10.1016/j.tet.2007.12.004
• 作为产物：
  描述：

  N-benzyloxy-N-(2-(benzyloxycarbonyl)ethyl) acryl amide 、 二乙醇胺 以 乙醇 为溶剂， 反应 24.0h， 以60%的产率得到N-benzyloxy-N-(2-(benzyloxycarbonyl)ethyl) 3-bis(2'-hydroxyethyl)aminopropionamide
  参考文献：
  名称：

  Mixed catechol-hydroxamate and catechol-(o-hydroxy)phenacyl siderophores: synthesis and uptake studies with receptor-deficient Escherichia coli mutants

  摘要：

  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.

  DOI：

  10.1016/j.tet.2007.12.004

文献信息

• 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.