2-[(4-硝基苯基)氨基]乙醇 | 1965-54-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-[(4-硝基苯基)氨基]乙醇
• 英文名称: N-(2-hydroxyethyl)-4-nitroaniline
• 英文别名: 2-(4-nitrophenylamino)ethanol；2-((4-nitrophenyl)amino)ethan-1-ol；N-(2-Hydroxyaethyl)-p-nitroanilin；2-<4-Nitro-anilino>-aethanol；N-<4-Nitro-phenyl>-aethanolamin；N-(2-hydroxyethyl)-4-nitrobenzenamine；2-[(4-Nitrophenyl)amino]ethanol；2-(4-nitroanilino)ethanol
• CAS: 1965-54-4
• 化学式: C₈H₁₀N₂O₃
• mdl: MFCD00156330
• 分子量: 182.179
• InChiKey: VPRLWNAMKBZKRR-UHFFFAOYSA-N

物化性质

• 熔点：
  111-111.5 °C
• 沸点：
  389.5±22.0 °C(Predicted)
• 密度：
  1.352±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  78.1
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2922199090

反应信息

• 作为反应物：
  描述：

  2-[(4-硝基苯基)氨基]乙醇 在 palladium on activated charcoal TEA 、 一水合肼 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 70.5h， 生成 N-(2-diethylaminoethyl)benzene-1,4-diamine
  参考文献：
  名称：

  Structure−Activity Relationship of Quinoline Derivatives as Potent and Selective α_2C-Adrenoceptor Antagonists

  摘要：

  Starting from two acridine compounds identified in a high-throughput screening campaign (1 and 2, Table 1), a series of 4-aminoquinolines was synthesized and tested for their properties on the human alpha(2)-adrenoceptor subtypes (alpha(2A), alpha(2B), and alpha(2C.)). A number of compounds with good antagonist potencies against the alpha(2C)-adrenoceptor and excellent subtype selectivities over the other two subtypes were discovered. For example, (R)-{4-[4-(3,4-dimethylpiperazin-1-yl) phenylamino] quinolin- 3- yl} methanol 6j had an antagonist potency of 8.5 nM against, and a subtype selectivity of more than 200-fold for, the alpha(2C)-adrenoceptor. Investigation of the structure-activity relationship identified a number of structural features, the most critical of which was an absolute need for a substituent in the 3-position of the quinoline ring. The 3-position on the piperazine ring was also found to play an appreciable role, as substitutions in that position exerted a significant and stereospecific beneficial effect on the alpha(2C)-adrenoceptor affinity and potency. Replacing the piperazine ring proved difficult, with 1,4-diazepanes representing the only viable alternative.

  DOI：

  10.1021/jm060262x
• 作为产物：
  描述：

  4-硝基苯氧乙酸 在 18-冠醚-6 、 水 、 potassium hydride 、 N,N'-羰基二咪唑 作用下， 反应 1.5h， 生成 2-[(4-硝基苯基)氨基]乙醇
  参考文献：
  名称：

  Alkoxide-accelerated Smiles rearrangements. Synthesis of N-(2-hydroxyethyl)anilines from N-(2-hydroxyethyl)(aryloxy)acetamides

  摘要：

  DOI：

  10.1021/jo00173a076

文献信息

• New Uses for the Burgess Reagent in Chemical Synthesis: Methods for the Facile and Stereoselective Formation of Sulfamidates, Glycosylamines, and Sulfamides
  作者：K. C. Nicolaou、Scott A. Snyder、Deborah A. Longbottom、Annie Z. Nalbandian、Xianhai Huang

  DOI：10.1002/chem.200400503

  日期：2004.11.19

  Although the Burgess reagent (methoxycarbonylsulfamoyltriethylammonium hydroxide, inner salt) has found significant use in chemical synthesis as a dehydrating agent, almost no work has been directed towards its potential in other synthetic applications. As this article will detail, we have found that the Burgess reagent is remarkably effective at accomplishing a number of non-dehydrative synthetic

  尽管Burgess试剂（甲氧基羰基氨磺酰基三乙铵氢氧化物，内盐）已发现在化学合成中作为脱水剂具有重要用途，但几乎没有工作针对其在其他合成应用中的潜力。正如本文将要详细介绍的那样，我们发现，将Burgess试剂应用于适当的底物上，例如从1,2-二醇或环氧醇，α-和C-形成氨基磺酸盐时，在完成许多非脱水合成任务方面非常有效。来自碳水化合物的β-糖胺和来自1,2-氨基醇的环状磺酰胺 除了描述这些新反应歧管的功能之外，我们还描述了一组替代的Burgess型试剂的构造，这些试剂进一步扩展了这些新反应的范围。
• Copper(II)-Catalyzed C–N Coupling of Aryl Halides and N-Nucleophiles Promoted by Quebrachitol or Diethylene Glycol
  作者：Fangyu Du、Qifan Zhou、Yang Fu、Yuanguang Chen、Ying Wu、Guoliang Chen

  DOI：10.1055/s-0039-1690707

  日期：2019.12

  Herein, we report the natural ligand quebrachitol (QCT) as a promoter for a Cu(II) catalyst, which is highly effective for N-arylation of various amines and related aryl halides. A series of diarylamine derivatives were obtained in high yields by using diethylene glycol (DEG) as both ligand and solvent. The C–N coupling reactions proceed under mild conditions and exhibit good functional group tolerance

  在本文中，我们报告了天然配体 quebrachitol (QCT) 作为 Cu(II) 催化剂的促进剂，它对各种胺和相关芳基卤化物的 N-芳基化非常有效。通过使用二甘醇（DEG）作为配体和溶剂，以高收率获得了一系列二芳胺衍生物。C-N偶联反应在温和的条件下进行并表现出良好的官能团耐受性。
• Cu(II)-Catalyzed C-N Coupling of (Hetero)aryl Halides and N-Nucleophiles Promoted by α-Benzoin Oxime
  作者：Chunling Yuan、Lei Zhang、Yingdai Zhao

  DOI：10.3390/molecules24224177

  日期：——

  We first reported the new application of a translate metal chelating ligand α-benzoin oxime for improving Cu-catalyzed C-N coupling reactions. The system could catalyse coupling reactions of (hetero)aryl halides with a wide of nucleophiles (e.g., azoles, piperidine, pyrrolidine and amino acids) in moderate to excellent yields. The protocol allows rapid access to the most common scaffolds found in FDA-approved pharmaceuticals.

  我们首次报道了一种新的应用于改进铜催化的C-N偶联反应的金属螯合配体α-苯甲醛肟。该体系能够催化(hetero)芳基卤代物与各种亲核试剂（例如唑类化合物、哌啶、吡咯啉和氨基酸）的偶联反应，产率从中等到优良不等。该方案可快速获得FDA批准的药物中常见的骨架。
• Synthesis of non-symmetrical sulfamides using burgess-type reagents
  申请人：The Scripps Research Institute

  公开号：US20040138448A1

  公开（公告）日：2004-07-15

  A practical and high-yielding method for the efficient, one-step synthesis of diverse classes of N,N′-differentiated sulfamides employs a wide range of amino alcohols and simple amines using Burgess-type reagents. This methodology extends the application and availability of sulfamides within the fields of chemical biology, medicinal chemistry, asymmetric synthesis, and supramolecular chemistry.

  一种实用且高产的方法，用于高效、一步合成多种类别的N,N′-差异化磺酰胺，利用广泛的氨基醇和简单胺类，使用伯吉斯型试剂。这种方法扩展了磺酰胺在化学生物学、药物化学、不对称合成和超分子化学领域的应用和可用性。
• Organosilicon polymers, and dyes, exhibiting nonlinear optical response
  申请人：Hercules Incorporated

  公开号：US05663308A1

  公开（公告）日：1997-09-02

  Organosilicon polymers, including crosslinked polymers and crosslinkable prepolymers, of cyclic polysiloxane, organic dyes, and, optionally, polyenes. The dyes include those with delocalized Pi electron systems linking electron donor groups and electron acceptor groups, and with at least two carbon-carbon double bond-containing pendant groups attached to at least two different sites from among the indicated delocalized Pi electron systems, donor groups, and acceptor groups.

  有机硅聚合物，包括环状聚硅氧烷、有机染料和可交联预聚物，以及可选的聚烯烃。这些染料包括具有离域π电子系统的染料，连接电子给体基团和电子受体基团，并且至少有两个碳-碳双键含有的挂链基团，连接至所述离域π电子系统、给体基团和受体基团中的至少两个不同位置。

表征谱图