2,4-二氯-1-苯氧基-苯 | 51892-26-3

• 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: 2,4-二氯-1-苯氧基-苯
• 中文别名: 9H-芴-9-基甲基3-氰基哌啶-1-羧酸酯
• 英文名称: 2,4-dichloro-diphenyl ether
• 英文别名: 2,4-Dichlor-diphenylaether；2,4-Dichlorodiphenyl ether；2,4-dichloro-1-phenoxybenzene
• CAS: 51892-26-3
• 化学式: C₁₂H₈Cl₂O
• 分子量: 239.101
• InChiKey: KXIPYLZZJZMMPD-UHFFFAOYSA-N

物化性质

• 溶解度：
  2.34e-05 M
• 蒸汽压力：
  9.20e-04 mmHg
• 保留指数：
  1693.3

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  15
• 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：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2909309090

反应信息

• 作为产物：
  描述：

  (2,4-dichlorophenoxy)-tetraphenyl-λ5-stibane 反应 2.0h， 以90%的产率得到2,4-二氯-1-苯氧基-苯
  参考文献：
  名称：

  Synthesis, structure, and thermal destruction of aroxytetraphenylstiboranes

  摘要：

  A series of aroxytetraphenylstiboranes, Ph(4)SbOAr, were obtained by the reaction of pentaphenylstiborane with phenols at similar to 20 degrees C. The thermolysis of these compounds gives O- or o-C-phenylation products. The thermolysis of stiboranes, which incorporate aryl groups containing electron-withdrawing substituents (Ar = 2,4-Br-2, 2,4-Cl-2, 2-NO2, 4-OPh) produces predominantly simple diaryl ethers of asymmetric structure in 58%, 90%, 32%, and 60% yields, respectively.

  DOI：

  10.1007/bf00696931

文献信息

• Fe₃ O₄ @SiO₂ -copper sucrose xanthate as a green nanocatalyst for N-, O- and S-arylation
  作者：Iman Radfar、Maryam Kazemi Miraki、Naghmeh Esfandiary、Leila Ghandi、Akbar Heydari

  DOI：10.1002/aoc.4619

  日期：2019.1

  Formation of C(sp2)–X bonds was carried out using a Fe3O4@SiO2‐copper(I) sucrose xanthate nanoparticle catalyst with the aid of the copper(I) xanthate moiety in the catalyst which was prepared from the reaction between sucrose and carbon disulfide through an alkaline medium via the traditional Zeise approach. Various techniques were employed for the characterization of these novel nanoparticles. Three

  C（sp 2）–X键的形成是利用Fe 3 O 4 @SiO 2－铜（I）蔗糖黄原酸酯纳米颗粒催化剂，借助由该催化剂制备的催化剂中的黄原酸铜（I）部分进行的。传统的Zeise方法通过碱性介质使蔗糖和二硫化碳之间发生反应。各种技术被用于表征这些新颖的纳米颗粒。三种杂原子N，O和S成功地进行了杂原子芳基化反应，分别生成仲胺或叔胺，醚和硫醚。
• Ullmann diaryl ether synthesis catalyzed by copper (I)/pyridine-functionalized silane
  作者：Baohua Zhang、Lanxiang Shi、Ruixia Guo、Sijie Liu

  DOI：10.1080/10426507.2015.1119135

  日期：2016.6.2

  GRAPHICAL ABSTRACT ABSTRACT Ullmann-type diaryl ether synthesis was performed under mild conditions in DMF/K2CO3 using a pyridine-functionalized silane as a ligand. The products were obtained in good yields. This method tolerates a variety of functional groups and is effective in the synthesis of hindered diaryl ethers and heteroaryl ethers.

  图形摘要 摘要 Ullmann 型二芳基醚合成在温和条件下在 DMF/K2CO3 中使用吡啶官能化硅烷作为配体进行。以良好的收率获得了产物。该方法耐受多种官能团，在受阻二芳基醚和杂芳基醚的合成中有效。
• Mild Conditions for Copper-Catalyzed Coupling Reaction of Phenols and Aryl Iodides and Bromides
  作者：Armelle Ouali、Jean-Francis Spindler、Henri-Jean Cristau、Marc Taillefer

  DOI：10.1002/adsc.200505385

  日期：2006.3

  be efficiently performed by means of catalytic amounts of copper iodide and the inexpensive ligand 1 (structure given in Table 1). The reaction is applicable to a wide range of substrates and proceeds at 60–80 °C, the lowest temperatures reported to date for an Ullmann-type synthesis of diaryl ethers. Moreover, the use of aryl bromides and inexpensive K3PO4 as base make this method attractive for applications

  苯酚和芳基溴化物的偶联可通过催化量的碘化铜和廉价的配体1（表1中给出的结构）有效地进行。该反应适用于多种底物，反应温度为60–80°C，这是迄今为止报道的Ullmann型二芳基醚合成的最低温度。此外，使用芳基溴化物和廉价的K 3 PO 4作为碱使得该方法对于工业规模的应用具有吸引力。
• A General and Mild Ullmann-Type Synthesis of Diaryl Ethers
  作者：Henri-Jean Cristau、Pascal P. Cellier、Samy Hamada、Jean-Francis Spindler、Marc Taillefer

  DOI：10.1021/ol036290g

  日期：2004.3.1

  [reaction: see text] An efficient method for the synthesis of diaryl ethers under particularly mild conditions is described. Inexpensive ligands were found to greatly accelerate the Ullmann-type coupling of aryl bromides or iodides with phenols. A series of diaryl ethers were obtained with excellent yields in acetonitrile in the presence of Cs(2)CO(3) and catalytic copper(I) oxide. The reaction tolerates

  [反应：见正文]描述了一种在特别温和的条件下合成二芳基醚的有效方法。发现廉价的配体极大地促进了芳基溴化物或碘化物与苯酚的乌尔曼型偶联。在Cs（2）CO（3）和氧化铜（I）的存在下，在乙腈中以优异的收率获得了一系列二芳基醚。该反应容许具有不利取代模式的底物，例如空间受阻的偶联配偶体或富电子的芳基卤化物。
• Nitrogen Ligands in Copper-Catalyzed Arylation of Phenols: Structure/Activity Relationships and Applications
  作者：Armelle Ouali、Jean-Francis Spindler、Anny Jutand、Marc Taillefer

  DOI：10.1002/adsc.200600628

  日期：2007.8.6

  importance of ligand/copper-catalyzed arylations of nucleophiles in organic chemistry, the structural and electronic features that make a ligand efficient in these reactions have not been determined until now. In this work, several bidentate ligands involving pyridine and/or imine nitrogen binding sites such as our lead ligand 1 have been synthesized, and tested in phenol arylations with a view to

  尽管在有机化学中亲核体的配体/铜催化的芳基化很重要，但到目前为止，尚未确定使配体在这些反应中有效的结构和电子特征。在这项工作中，已经合成了几个涉及吡啶和/或亚胺氮结合位点的二齿配体，例如我们的先导配体1，并在苯酚芳基化中进行了测试，以突出螯合物的结构与其功效之间的关系。这项研究使我们能够更精确地定义每个类型为N的作用-在催化过程中结合位点，并发现新的有效的配体。其中，亚氨基吡啶6a廉价且易于高收率制备，对于工业应用非常有吸引力。这里介绍了其应用领域的一些示例。将来，这项工作的发展可能允许在芳基化反应中更合理地设计有效配体，而无需借助经典的配体筛选。