4-(2-氨基乙基)-5-硝基苯-1,2-二醇 | 21581-49-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 4-(2-氨基乙基)-5-硝基苯-1,2-二醇
• 英文名称: 4-(2-aminoethyl)-5-nitrobenzene-1,2-diol
• 英文别名: 2-nitrodopamine；6-nitrodopamine；nitrodopamine；ND；5-nitrodopamine；6-Nitrodopamin；1,2-Benzenediol, 4-(2-aminoethyl)-5-nitro-
• CAS: 21581-49-7
• 化学式: C₈H₁₀N₂O₄
• 分子量: 198.178
• InChiKey: GAWRYVJRKWPEFX-UHFFFAOYSA-N

物化性质

• 溶解度：
  可溶于DMSO（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(2-氨基乙基)-5-硝基苯-1,2-二醇 在 三乙胺 、 sodium hydroxide 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 20.0h， 生成 N-(4,5-dihydroxy-2-nitrophenethyl)octanamide
  参考文献：
  名称：

  Radiofluorinated N-Octanoyl Dopamine ([¹⁸F]F-NOD) as a Tool To Study Tissue Distribution and Elimination of NOD in Vitro and in Vivo

  摘要：

  To mitigate pretransplantation injury in organs of potential donors, N-octanoyl dopamine (NOD) treatment might be considered as it does not affect hemodynamic parameters in braindead (BD) donors. To better assess optimal NOD concentrations for donor treatment, we report on the fast and facile radiofluorination of the NOD-derivative [F-18]F-NOD [F-18]5 for in vivo assessment of NOD's elimination kinetics by means of PET imaging. [F-18]5 was synthesized in reproducibly high radiochemical yields and purity (>98%) as well as high specific activities (>20 GBq/mu mol). Stability tests showed no decomposition of [F-18]5 over a period of 120 min in rat plasma. In-vitro, low cell association was found for [F-18]5, indicating no active transport mechanism into cells. In vivo, [F-18]5 exhibited a fast blood clearance and a predominant hepatobiliary elimination. As these data suggest that also NOD might be cleared fast, further pharmacokinetic evaluation is warranted.

  DOI：

  10.1021/acs.jmedchem.6b01191
• 作为产物：
  描述：

  盐酸多巴胺 在 硫酸 、 sodium nitrite 作用下， 以 水 为溶剂， 以77%的产率得到4-(2-氨基乙基)-5-硝基苯-1,2-二醇
  参考文献：
  名称：

  生物启发的水下粘合和按需脱胶

  摘要：

  贻贝胶：据报道，受生物启发的水下化学键合具有光触发脱胶的可能性。合成了由硝基多巴胺末端官能化的四臂星形聚乙二醇。硝基多巴胺提供了邻苯二酚的反应性和可光裂解的邻硝基苯乙基的化学性质（见图）。

  DOI：

  10.1002/anie.201108629

文献信息

• [EN] METAL NANOPARTICLE SURFACE LIGAND REPLACEMENT METHOD<br/>[FR] PROCÉDÉ DE REMPLACEMENT DE LIGAND DE SURFACE DE NANOPARTICULE MÉTALLIQUE
  申请人：UNIV WIEN BODENKULTUR

  公开号：WO2018091666A1

  公开（公告）日：2018-05-24

  The invention relates to a method of producing inorganic nanoparticles with a polar surface, a) providing an inorganic nanoparticle with a coordinated organic ligand to the nanoparticles surface, b) providing a replacement salt comprising a replacement ion and a counterion, c) treating the inorganic nanoparticle with the coordinated organic ligand with the replacement salt in the presence of a chelating agent that complexes the counterion, thereby increasing the replacements ion's reactivity and replacing the organic ligand on the nanoparticle surface by the replacement ion which results in an inorganic nanoparticle with a polar surface; and a kit.

  这项发明涉及一种制备具有极性表面的无机纳米颗粒的方法，a)提供具有配位有机配体的无机纳米颗粒至纳米颗粒表面，b)提供包括替代离子和对离子的替代盐，c)在存在络合剂的情况下，用替代盐处理具有配位有机配体的无机纳米颗粒，络合剂络合对离子，从而增加替代离子的反应性并通过替代离子替换纳米颗粒表面上的有机配体，从而得到具有极性表面的无机纳米颗粒；以及一个试剂盒。
• Multifunctional microparticles with uniform magnetic coatings and tunable surface chemistry
  作者：Tobias P. Niebel、Florian J. Heiligtag、Jessica Kind、Michele Zanini、Alessandro Lauria、Markus Niederberger、André R. Studart

  DOI：10.1039/c4ra09698c

  日期：——

  Microplatelets and fibers that can be manipulated using external magnetic fields find potential applications as miniaturized probes, micromirrors in optical switches, remotely actuated micromixers and tunable reinforcements in composite materials. Controlling the surface chemistry of such microparticles is often crucial to enable full exploitation of their mechanical, optical and sensorial functions. Here, we report a simple and versatile procedure to directly magnetize and chemically modify the surface of inorganic microplatelets and polymer fibers of inherently non-magnetic compositions. As opposed to other magnetization approaches, the proposed non-aqueous sol–gel route enables the formation of a dense and homogeneous coating of superparamagnetic iron oxide nanoparticles (SPIONs) on the surface of the microparticles. Such coating provides a suitable platform for the direct chemical functionalization of the microparticles using catechol-based ligands displaying high affinity towards iron oxide surfaces. By adsorbing for example nitrodopamine palmitate (ND-PA) on the surface of hydrophilic magnetite-coated alumina platelets (Fe3O4@Al2O3) we can render them sufficiently surface active to generate magnetically responsive Pickering emulsions. We also show that microplatelets and fibers coated with a uniform iron oxide layer can be easily manipulated using low magnetic fields despite their intrinsic non-magnetic nature. These examples illustrate the potential of the proposed approach in generating functional, magnetically responsive microprobes and building blocks for several emerging applications.

  利用外部磁场操控微型板状物和纤维，有望作为微型探针、光学开关中的微镜、远程驱动的微混合器以及复合材料中可调增强材料。控制这类微粒的表面化学性质，往往对充分发挥其力学、光学和传感功能至关重要。在此，我们报道了一种简便且通用的方法，直接磁化并化学改性原本非磁性组成的无机微板状物和聚合物纤维的表面。与其它磁化方法不同，这一提出的非水相溶胶-凝胶路线使得超顺磁性氧化铁纳米粒子（SPIONs）在微粒表面形成致密且均匀的涂层。这样的涂层为一个适宜的平台，可利用对氧化铁表面显示出高亲和性的基于邻苯二酚的配体，直接对微粒进行化学功能化。例如，通过吸附硝基多巴胺棕榈酸酯（ND-PA）在亲水性的磁铁矿涂层氧化铝片（Fe3O4@Al2O3）表面，我们能使它们表面活性足够强，从而生成磁响应性的Pickering乳液。我们还展示出，即使微板状物和纤维本身不具有磁性，一个均匀的氧化铁涂层足以让它们在低磁场下轻松操控。这些例子展示了所提出方法在生成具备磁响应性的功能性微探针，以及多个新兴应用中的构建模块的潜力。
• Synthesis and Characterization of Bifunctional Compounds:  Templates for Metal Crown Ether Assemblies
  作者：D. Luke Nelsen、Peter S. White、Michel R. Gagné

  DOI：10.1021/om050639h

  日期：2005.10.1

  (dppe)Pd-salicylimine cations and (dppe)Pd-catecholate complexes with dangling primary ammonium ions are excellent donors for 18-crown-6 (18-c-6) and benzo-18-c-6 receptors. The self-assembly of these host−guest complexes from their constituent components is efficient, and two X-ray-generated structures showing atom connectivity are reported. A discussion of N-imine isomers of the Schiff base-derived

  （dppe）Pd-水杨酰亚胺阳离子和（dppe）Pd-儿茶酚酸酯配合物与悬空的伯铵离子是18冠6（18-c-6）和苯并18-c-6受体的优良供体。这些主客体络合物从其组成成分的自组装是有效的，并且报道了两个显示原子连通性的X射线产生的结构。还包括了席夫碱衍生的4-氨基苄胺的N-亚胺异构体的讨论。
• Catechol reactivity: Synthesis of dopamine derivatives substituted at the 6-position
  作者：Jennifer C. Rote、Sarah N. Malkowski、C. Skyler Cochrane、Gabrielle E. Bailey、Noah S. Brown、Mauricio Cafiero、Larryn W. Peterson

  DOI：10.1080/00397911.2016.1269350

  日期：2017.3.4

  catechol core can modulate its stereoelectronic properties, the acidity of its phenolic hydroxyl groups, and the overall hydrophobicity of the molecule. Herein, we report the synthesis of a series of four novel dopamine analogues substituted at the 6-position of catechol core. The 1H NMR chemical shift of the aromatic proton meta to the substituent correlated strongly with the Hammett σm constant, confirming

  摘要 多巴胺是一种普遍存在的神经递质，对人体的正常运作至关重要。除了这一关键作用之外，儿茶酚胺核心还显示出可用作多种药物和其他应用（如金属检测和粘合材料）的支架。多巴胺儿茶酚核心 6 位的取代基可以调节其立体电子特性、酚羟基的酸度和分子的整体疏水性。在此，我们报告了在儿茶酚核心的 6 位取代的一系列四种新型多巴胺类似物的合成。芳族质子间位到取代基的 1H NMR 化学位移与哈米特 σm 常数密切相关，证实了取代基的电子特性。图形概要
• Nitration of catecholamines with nitrogen oxides in mild conditions: a hypothesis for the reactivity of NO in physiological systems
  作者：Marie-Laure de la Bretèche、Claudine Servy、Maryse Lenfant、Claire Ducrocq

  DOI：10.1016/0040-4039(94)85368-1

  日期：1994.9

  Dopamine, norepinephrine and epinephrine react at room temperature, in acetate buffer (36) with sodium nitrite or in non-deaerated phosphate buffer (pH 7.4) with NO. The corresponding 6-nitro derivatives are formed.

  多巴胺，去甲肾上腺素和肾上腺素在室温下于乙酸缓冲液（36）中与亚硝酸钠反应，或在非脱气磷酸盐缓冲液（pH 7.4）中与NO反应。形成相应的6-硝基衍生物。