O-benzyl-N-(tert-butoxycarbonyl)-N-(1-pyrenyl)hydroxylamine | 177859-59-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: O-benzyl-N-(tert-butoxycarbonyl)-N-(1-pyrenyl)hydroxylamine
• 英文别名: tert-butyl N-phenylmethoxy-N-(pyren-1-ylmethyl)carbamate
• CAS: 177859-59-5
• 化学式: C₂₉H₂₇NO₃
• 分子量: 437.538
• InChiKey: FIKJHIMFYPBDOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  O-benzyl-N-(tert-butoxycarbonyl)-N-(1-pyrenyl)hydroxylamine 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以89%的产率得到N-phenylmethoxy-1-pyren-1-ylmethanamine
  参考文献：
  名称：

  Fluorescent, Siderophore-Based Chelators. Design and Synthesis of a Trispyrenyl Trishydroxamate Ligand, an Intramolecular Excimer-Forming Sensing Molecule Which Responds to Iron(III) and Gallium(III) Metal Cations

  摘要：

  Two pyrene-labeled hydroxylamines, 5-Bn and 5-Bz, O-protected with the benzyl and the benzoyl group, respectively, have been prepared for the generation of siderophore-based new chelators incorporating both the pyrene chromophore and the hydroxamic acid functionality. 5-Bz formed the starting point toward the synthesis of the tripod-shaped trishydroxamate, 1. That trichromophoric ligand displays remarkable fluorescence emission properties (dual emission: ''monomer'' and excimer type) which are markedly and selectively modified by binding Fe(NO3)(3) and Ga(NO3)(3). Ferric ions induce a quasi total quenching of the pyrene fluorescence, whereas the nonquenching Ga(III) cations are observed to affect the value of the excimer-to-monomer fluorescence intensity ratio. Ethylenediaminetetraacetic acid (EDTA) competition reactions yielded an estimated value of 3.8 for log K* of the complex LFe in methanol/water (80/20 v/v), where K* = ([LFe][H+](3)/([LH(3)][Fe3+]) and L is the ligand in its totally deprotonated form. Compound 1 is the prototype of a new class of photoresponsive molecular systems which could act as sensitive probes for metal cation detection and recognition.

  DOI：

  10.1021/jo960191h
• 作为产物：
  描述：

  1-氯甲基芘 、 N-(苄氧基)氨基甲酸叔丁酯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以71%的产率得到O-benzyl-N-(tert-butoxycarbonyl)-N-(1-pyrenyl)hydroxylamine
  参考文献：
  名称：

  Fluorescent, Siderophore-Based Chelators. Design and Synthesis of a Trispyrenyl Trishydroxamate Ligand, an Intramolecular Excimer-Forming Sensing Molecule Which Responds to Iron(III) and Gallium(III) Metal Cations

  摘要：

  Two pyrene-labeled hydroxylamines, 5-Bn and 5-Bz, O-protected with the benzyl and the benzoyl group, respectively, have been prepared for the generation of siderophore-based new chelators incorporating both the pyrene chromophore and the hydroxamic acid functionality. 5-Bz formed the starting point toward the synthesis of the tripod-shaped trishydroxamate, 1. That trichromophoric ligand displays remarkable fluorescence emission properties (dual emission: ''monomer'' and excimer type) which are markedly and selectively modified by binding Fe(NO3)(3) and Ga(NO3)(3). Ferric ions induce a quasi total quenching of the pyrene fluorescence, whereas the nonquenching Ga(III) cations are observed to affect the value of the excimer-to-monomer fluorescence intensity ratio. Ethylenediaminetetraacetic acid (EDTA) competition reactions yielded an estimated value of 3.8 for log K* of the complex LFe in methanol/water (80/20 v/v), where K* = ([LFe][H+](3)/([LH(3)][Fe3+]) and L is the ligand in its totally deprotonated form. Compound 1 is the prototype of a new class of photoresponsive molecular systems which could act as sensitive probes for metal cation detection and recognition.

  DOI：

  10.1021/jo960191h

文献信息

• Fluorescent, Siderophore-Based Chelators. Design and Synthesis of a Trispyrenyl Trishydroxamate Ligand, an Intramolecular Excimer-Forming Sensing Molecule Which Responds to Iron(III) and Gallium(III) Metal Cations
  作者：Frédéric Fages、Bruno Bodenant、Tanja Weil

  DOI：10.1021/jo960191h

  日期：1996.1.1

  Two pyrene-labeled hydroxylamines, 5-Bn and 5-Bz, O-protected with the benzyl and the benzoyl group, respectively, have been prepared for the generation of siderophore-based new chelators incorporating both the pyrene chromophore and the hydroxamic acid functionality. 5-Bz formed the starting point toward the synthesis of the tripod-shaped trishydroxamate, 1. That trichromophoric ligand displays remarkable fluorescence emission properties (dual emission: ''monomer'' and excimer type) which are markedly and selectively modified by binding Fe(NO3)(3) and Ga(NO3)(3). Ferric ions induce a quasi total quenching of the pyrene fluorescence, whereas the nonquenching Ga(III) cations are observed to affect the value of the excimer-to-monomer fluorescence intensity ratio. Ethylenediaminetetraacetic acid (EDTA) competition reactions yielded an estimated value of 3.8 for log K* of the complex LFe in methanol/water (80/20 v/v), where K* = ([LFe][H+](3)/([LH(3)][Fe3+]) and L is the ligand in its totally deprotonated form. Compound 1 is the prototype of a new class of photoresponsive molecular systems which could act as sensitive probes for metal cation detection and recognition.