O-benzoyl-N-(1-pyrenyl)hydroxylamine | 177859-62-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: O-benzoyl-N-(1-pyrenyl)hydroxylamine
• 英文别名: (Pyren-1-ylmethylamino) benzoate
• CAS: 177859-62-0
• 化学式: C₂₄H₁₇NO₂
• 分子量: 351.404
• InChiKey: SYTXSOPDIDZFMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5,11,17,23-tetra-tert-butyl-25,27-dichloroformylmethoxy-26,28-dimethoxycalix[4]arene 、 O-benzoyl-N-(1-pyrenyl)hydroxylamine 在 吡啶 作用下， 以 四氢呋喃 为溶剂， 以21%的产率得到5,11,17,23-tetra(tert-butyl)-26,28-bis[N-(benzoyloxy)-N-(1-pyrenylmethyl)aminocarbonylmethoxy]-25,27-dimethoxycalix[4]arene
  参考文献：
  名称：

  Synthesis and Solution Structure Analysis of a Bispyrenyl Bishydroxamate Calix[4]arene-Based Receptor, a Fluorescent Chemosensor for Cu²⁺ and Ni²⁺ Metal Ions

  摘要：

  A bispyrenyl calix[4]arene-based receptor, 1, incorporating two hydroxamic acid functionalities has been designed for the optical detection of Cu2+ and Ni2+ metal ions in solution. The synthetic route is based on the utilization of pyrene-labeled, O-protected hydroxylamines that represent versatile building blocks for the generation of fluorescent siderophore-based chelators. Compound 1 is shown to exist in CDCl3 solution at room temperature as a mixture of mainly two conformers, namely, the cone and partial-cone species (partial-cone/cone ratio ca. 57/43). The full assignment of the proton and carbon resonances of the calix[4]arene core for both conformers is described. Ligand 1 exhibited in solution a dual fluorescence emission spectrum composed of monomer and excimer contributions, the latter resulting from intramolecular interactions between pyrene nuclei in the excited state. In methanol/water (80/20 v/v), the fluorescence intensity was shown to be sensitive to-proton concentration and to the presence of transition-metal ions. Addition of Cu2+ and Ni2+ metal cations induced a dramatic quenching of fluorescence of 1 depending on the value of -log[H+]. The excimer-forming photoresponsive ligand 1 belongs to a new class of sensitive chemosensors for the selective detection of transition-metal species in aqueous media.

  DOI：

  10.1021/jo9904720
• 作为产物：
  描述：

  tert-butyl (benzoyloxy)carbamate 在 盐酸 、 sodium hydride 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 O-benzoyl-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