N-formylmethyl 2,3-dibenzyloxybenzamide | 909704-32-1

• 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: N-formylmethyl 2,3-dibenzyloxybenzamide
• 英文别名: N-(2-oxoethyl)-2,3-bis(phenylmethoxy)benzamide
• CAS: 909704-32-1
• 化学式: C₂₃H₂₁NO₄
• 分子量: 375.424
• InChiKey: LOIPTBOIHNTODS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-formylmethyl 2,3-dibenzyloxybenzamide 、 2-(2',3'-dibenzyloxyphenyl)-1-[3'-di(2''-hydroxyethyl)amino]propenoyl-4,5-dihydroimidazole 、 (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2-(2',3'-dibenzyloxyphenyl)-1-{3'-di-[8''-aza-3''-oxa-4'',9''-dioxo-9''-(2''',3'''-dibenzyloxyphenyl)non-5''-enyl]amino}propanoyl-4,5-dihydroimidazole
  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：

  苯甲酸,二羟基- 在 吡啶 、 盐酸 、 甲醇 、 sodium hydroxide 、 氯化亚砜 、 potassium carbonate 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 20.5h， 生成 N-formylmethyl 2,3-dibenzyloxybenzamide
  参考文献：
  名称：

  Conjugates of methyl 6-aminopenicillanate with biscatechol-hydroxamate chelators: synthesis and siderophoric activity

  摘要：

  A synthesis of biscatechol-hydroxamate and triscatechol chelators and of conjugates of the former with methyl 6-aminopenicillanate is described. It is based on the multiple use of the ylide Ph3PCCO as a C-2 building block in one-pot coupling reactions between aldehydes and alcohols or amines. These conjugates were actively internalized into siderophore-deficient Escherichia coli mutant H5596. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.05.056

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.
• Conjugates of methyl 6-aminopenicillanate with biscatechol-hydroxamate chelators: synthesis and siderophoric activity
  作者：Rainer Schobert、Andreas Stangl、Kerstin Hannemann

  DOI：10.1016/j.tet.2006.05.056

  日期：2006.8

  A synthesis of biscatechol-hydroxamate and triscatechol chelators and of conjugates of the former with methyl 6-aminopenicillanate is described. It is based on the multiple use of the ylide Ph3PCCO as a C-2 building block in one-pot coupling reactions between aldehydes and alcohols or amines. These conjugates were actively internalized into siderophore-deficient Escherichia coli mutant H5596. (c) 2006 Elsevier Ltd. All rights reserved.