2-溴-4'-硝基二苯醚 | 86607-76-3

• 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-溴-4'-硝基二苯醚
• 英文名称: 1-bromo-2-(4-nitrophenoxy)benzene
• CAS: 86607-76-3
• 化学式: C₁₂H₈BrNO₃
• mdl: MFCD02106046
• 分子量: 294.104
• InChiKey: CPZPDDSHJZQKSD-UHFFFAOYSA-N

物化性质

• 熔点：
  80-82 °C
• 沸点：
  351.5±22.0 °C(Predicted)
• 密度：
  1.563±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  55
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2909309090

反应信息

• 作为反应物：
  描述：

  2-溴-4'-硝基二苯醚 在 溴 、 碘 、 溶剂黄146 作用下， 生成 2,4-二溴-1-(4-硝基苯氧基)苯
  参考文献：
  名称：

  SOME DERIVATIVES OF DIPHENYL ETHER

  摘要：

  DOI：

  10.1021/ja01366a062
• 作为产物：
  描述：

  2-溴苯酚 、 对硝基氯苯 在 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 0.67h， 生成 2-溴-4'-硝基二苯醚
  参考文献：
  名称：

  Functionalized 2,1-benzothiazine 2,2-dioxides as new inhibitors of Dengue NS5 RNA-dependent RNA polymerase

  摘要：

  Over recent years, many RNA viruses have been "re-discovered", including life-threatening flaviviruses, such as Dengue, Zika, and several encephalitis viruses. Since no specific inhibitors are currently available to treat these infections, there is a pressing need for new therapeutics. Among the flaviviral proteins, NS5 RNA-dependent RNA polymerase (RdRp) represents a validated target being essential for viral replication and it has no human analog. To date, few NS5 RdRp inhibitor chemotypes have been reported and no inhibitors are currently in clinical development. In this context, after an in vitro screening against Dengue 3 NS5 RdRp of our in-house HCV NS5B inhibitors focused library, we found that 2,1-benzothiazine 2,2-dioxides are promising non-nucleoside inhibitors of flaviviral RdRp with compounds 8 and 10 showing IC50 of 0.6 and 0.9 mu M, respectively. Preliminary structure-activity relationships indicated a key role for the C-4 benzoyl group and the importance of a properly functionalized C-6 phenoxy moiety to modulate potency. Compound 8 acts as non-competitive inhibitor and its proposed pose in the so-called N pocket of the RdRp thumb domain allowed to explain the key contribution of the benzoyl and the phenoxy moieties for the ligand binding. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.10.064

文献信息

• Ultrasound-promoted intramolecular direct arylation in a capillary flow microreactor
  作者：Lei Zhang、Mei Geng、Peng Teng、Dan Zhao、Xi Lu、Jian-Xin Li

  DOI：10.1016/j.ultsonch.2011.07.008

  日期：2012.3

  An intramolecular direct arylation of various aryl bromides was performed using ultrasonic irradiation and a continuous flow capillary microreactor. The present procedure provided a higher functional group tolerance, ligand-free, milder reaction conditions and a shorter reaction time for the direct arylation compared with the conventional methods. The ultrasonic irritation not only greatly promoted

  使用超声波辐射和连续流动的毛细管微反应器进行各种芳基溴的分子内直接芳基化。与常规方法相比，本方法为直接芳基化提供了更高的官能团耐受性，无配体，更温和的反应条件和更短的反应时间。超声刺激不仅大大促进了直接芳基化反应的转化和选择性，而且解决了微反应器发生固相反应的堵塞问题，使反应顺利进行。
• Quinoline Ligands Improve the Classic Direct C−H Functionalisation/Intramolecular Cyclisation of Diaryl Ethers to Dibenzofurans
  作者：Katrina Mackey、David J. Jones、Leticia M. Pardo、Gerard P. McGlacken

  DOI：10.1002/ejoc.202001416

  日期：2021.1.22

  Intramolecular arylation through direct C−H functionalisation is a convenient method for the formation of dibenzofurans. In the Pd‐mediated process, the use of quinoline ligands alleviates a number of the existing issues with the use of phosphine ligands.

  通过直接CHH官能化进行的分子内芳基化是形成二苯并呋喃的便捷方法。在Pd介导的过程中，使用喹啉配体可缓解使用膦配体的许多现有问题。
• Palladium-catalysed cyclisation of 2-substituted halogenoarenes by dehydrohalogenation
  作者：D.E. Ames、A. Opalko

  DOI：10.1016/s0040-4020(01)91149-4

  日期：1984.1

  satisfactory system being palladium(II) acetate in NN-dimethylacetamide (DMA) with sodium carbonate as base) has been examined as a route to some heterocyclic systems. Whereas dehydrogenative cyclisation processes require stoichiometric amounts of palladium(II) reagent, the present procedure involves only catalytic amounts (0.1 molar proportion, or less), of palladium compound. The preparation of dibenzofuran

  已经研究了由各种钯催化剂和具有不同碱的溶剂（最普遍满意的体系是在碳酸钠为碱的NN-二甲基乙酰胺（DMA）中的乙酸钯（II））介导的环氢化卤化反应。尽管脱氢环化过程需要化学计量的钯（II）试剂，但本程序仅涉及催化量（0.1摩尔比例或更少）的钯化合物。二苯并呋喃，咔唑，芴酮，菲啶酮，6H-二苯并c，e] [l，2]噻嗪-5,5-二氧化物，6H-二苯并[b，d]吡喃和苯并呋喃并[2,3b]吡啶衍生物的制备方法为描述。3-苯甲酰胺基-2-氯吡啶环化为6-羟基苯并] [1,5]萘吡啶说明了该方法的区域特异性。
• Synthesis of Dibenzofurans Directly from Aryl Halides and ortho-Bromophenols via One-Pot Consecutive SNAr and Intramolecular Palladium-Catalyzed Aryl-Aryl Coupling Reactions
  作者：Hui Xu、Ling-Ling Fan

  DOI：10.1248/cpb.56.1496

  日期：——

  A series of dibenzofurans were efficiently and conveniently synthesized via one-pot consecutive C(sp(2))-O bond formation reaction (SNAr) in the presence of anhydrous K(2)CO(3), followed by C(sp(2))-C(sp(2)) bond formation reaction (intramolecular palladium-catalyzed aryl-aryl coupling reaction) between aryl halides and ortho-bromophenols. The desired dibenzofurans were obtained in 32-99% isolated

  在无水K（2）CO（3）存在下，通过一锅连续C（sp（2））-O键形成反应（SNAr），有效地合成了一系列二苯并呋喃，随后是C（sp（2 ））-C（sp（2））芳基卤化物和邻溴酚之间的键形成反应（分子内钯催化的芳基-芳基偶联反应）。以32-99％的分离产率获得所需的二苯并呋喃。
• One-pot Synthesis of Dibenzofurans via S_NAr and Subsequent Ligand-free Palladium-catalyzed Intramolecular Aryl-aryl Cross-coupling Reactions under Microwave Irradiation
  作者：Zhiping Che、Hui Xu

  DOI：10.1515/znb-2011-0808

  日期：2011.8.1

  An efficient one-pot synthesis of dibenzofurans, via SNAr reaction of aryl halides and ortho-bromophenols in the presence of anhydrous K₂CO₃ and subsequent ligand-free palladium-catalyzed intramolecular aryl-aryl cross-coupling cyclization under microwave irradiation, is described.

  通过在无水K2CO3存在下，对芳基卤代物和邻溴酚进行SNAr反应，并在微波辐射下进行无配体钯催化的分子内芳基-芳基交叉偶联环化反应，实现了二苯并呋喃的高效一锅合成。