benzyl 3-(benzyloxyamino)propionate | 88517-41-3

• 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: benzyl 3-(benzyloxyamino)propionate
• 英文别名: Benzyl 3-(phenylmethoxyamino)propanoate
• CAS: 88517-41-3
• 化学式: C₁₇H₁₉NO₃
• 分子量: 285.343
• InChiKey: WPCRSBBJKWDNDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl 3-(benzyloxyamino)propionate 、 丙烯酰氯 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以85%的产率得到N-benzyloxy-N-(2-(benzyloxycarbonyl)ethyl) acryl amide
  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：

  O-苄基羟胺 在 三氟甲磺酸三甲基硅酯 sodium hydroxide 作用下， 以 二氯甲烷 、 水 、 苯 为溶剂， 反应 4.0h， 生成 benzyl 3-(benzyloxyamino)propionate
  参考文献：
  名称：

  A convenient synthesis of N-benzyloxy-.BETA.-lactams via N-benzyloxyimines.

  摘要：

  N-苄氧基-β-内酰胺是通过将N-苄氧基亚胺与亚甲酸三甲硅酯在三甲基硅基三氟甲磺酸盐存在下反应随后进行环化，或与锂酯烯醇盐一步反应制备的。

  DOI：

  10.1248/cpb.37.1179

文献信息

• Facile synthesis of alkyl β-benzyloxyaminocarboxyolates related to monocyclic β-lactams.
  作者：Kiyoshi Ikeda、Kazuo Achiwa、Minoru Sekiya

  DOI：10.1016/s0040-4039(00)86233-4

  日期：1983.1

  N-Benzyloxyimines have been shown to react with ketene silyl acetals in the presence of trimethylsilyl triflate catalyst to give alkyl β-benzyloxyaminocarboxylates. Conversion of them to β-lactams has been exemplified.

  已显示在三氟甲磺酸三甲基甲硅烷基酯催化剂存在下，N-苄氧基氧亚甲基与乙烯酮甲硅烷基缩醛反应，生成烷基β-苄氧基氨基羧酸酯。已经举例说明了它们向β-内酰胺的转化。
• IKEDA, KIYOSHI;ACHIWA, KAZUO;SEKIYA, MINORU, CHEM. AND PHARM. BULL., 37,(1989) N, C. 1179-1184
  作者：IKEDA, KIYOSHI、ACHIWA, KAZUO、SEKIYA, MINORU

  DOI：——

  日期：——
• A convenient synthesis of N-benzyloxy-.BETA.-lactams via N-benzyloxyimines.
  作者：Kiyoshi IKEDA、Kazuo ACHIWA、Minoru SEKIYA

  DOI：10.1248/cpb.37.1179

  日期：——

  N-Benzyloxy-β-lactams were prepared from N-benzyloxyimines by reaction with ketene trimethylsilyl acetals in the presence of trimethylsilyl triflate followed by cyclization, or with lithium ester enolates in one step.

  N-苄氧基-β-内酰胺是通过将N-苄氧基亚胺与亚甲酸三甲硅酯在三甲基硅基三氟甲磺酸盐存在下反应随后进行环化，或与锂酯烯醇盐一步反应制备的。
• 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.