N-[2-(2',3'-dibenzyloxybenzamido)ethyl]-3-(bis[2'''-(3''''-N-benzyloxyacetamido)propanoyloxyethyl]amino)propionamide | 1013313-74-0

• 分子结构分类: 有机化合物 - 苯类化合物
• 英文名称: N-[2-(2',3'-dibenzyloxybenzamido)ethyl]-3-(bis[2'''-(3''''-N-benzyloxyacetamido)propanoyloxyethyl]amino)propionamide
• CAS: 1013313-74-0
• 化学式: C₅₄H₆₃N₅O₁₂
• 分子量: 974.121
• InChiKey: XTVATZMLJGWLAI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.21
• 重原子数：
  71.0
• 可旋转键数：
  31.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  191.58
• 氢给体数：
  2.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  N-[2-(2',3'-dibenzyloxybenzamido)ethyl]-3-(bis[2'''-(3''''-N-benzyloxyacetamido)propanoyloxyethyl]amino)propionamide 在 palladium on activated charcoal 氢气 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 7.0h， 以95%的产率得到N-[2-(2',3'-dihydroxybenzamido)ethyl]-3-(bis[2'''-(3''''-N-hydroxyacetamido)propanoyloxyethyl]amino)propionamide
  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-[2-(2',3'-dibenzyloxybenzamido)ethyl]-3''-bis(2'''-hydroxyethyl)aminopropionamide 、 3-[N-(benzyloxy)acetamido]propionic acid 在 氯甲酸乙酯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以56%的产率得到N-[2-(2',3'-dibenzyloxybenzamido)ethyl]-3-(bis[2'''-(3''''-N-benzyloxyacetamido)propanoyloxyethyl]amino)propionamide
  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