N-{4'-[di-[8''-aza-3''-oxa-4'',9''-dioxo-9''-(2''',3'''-dihydroxyphenyl)nonyl]amino]-4-oxobutyl}-2,3-(dihydroxy)benzamide | 1013313-91-1

• 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-{4'-[di-[8''-aza-3''-oxa-4'',9''-dioxo-9''-(2''',3'''-dihydroxyphenyl)nonyl]amino]-4-oxobutyl}-2,3-(dihydroxy)benzamide
• 英文别名: 2-[4-[(2,3-Dihydroxybenzoyl)amino]butanoyl-[2-[4-[(2,3-dihydroxybenzoyl)amino]butanoyloxy]ethyl]amino]ethyl 4-[(2,3-dihydroxybenzoyl)amino]butanoate
• CAS: 1013313-91-1
• 化学式: C₃₇H₄₄N₄O₁₄
• 分子量: 768.775
• InChiKey: MLCBYKKIVPCLOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  55
• 可旋转键数：
  23
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  282
• 氢给体数：
  9
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  N-{4'-[di-(8''-aza-3''-oxa-4'',9''-dioxo-9''-(2''',3'''-dibenzyloxyphenyl)non-5''-enyl)amino]-4'-oxobut-2-enyl}-2,3-(dibenzyloxy)benzamide 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 16.0h， 以92%的产率得到N-{4'-[di-[8''-aza-3''-oxa-4'',9''-dioxo-9''-(2''',3'''-dihydroxyphenyl)nonyl]amino]-4-oxobutyl}-2,3-(dihydroxy)benzamide
  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