phenyl o-tolyl selenide | 94800-50-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: phenyl o-tolyl selenide
• 英文别名: 2-methylphenyl phenyl selenide；2-tolyl phenyl selenide；2-tolyl-phenyl-selenide；phenyl 2-tolyl selenide；2-tolyl-phenylselenide；2-tolylphenylselenide；1-Methyl-2-(phenylselanyl)benzene；1-methyl-2-phenylselanylbenzene
• CAS: 94800-50-7
• 化学式: C₁₃H₁₂Se
• 分子量: 247.198
• InChiKey: XLKXWMZWJSGONP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.65
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为产物：
  描述：

  phenyl o-tolyl sulfone 在 selenium 作用下， 生成 phenyl o-tolyl selenide
  参考文献：
  名称：

  Chierici; Passerini, Atti della Accademia Nazionale dei Lincei, Classe di Scienze Fisiche, Matematiche e Naturali, Rendiconti, 1953, vol. <8> 15, p. 69,72

  摘要：

  DOI：

文献信息

• A Simple Copper Salt-Catalyzed Synthesis of Unsymmetrical Diaryl Selenides and Tellurides from Arylboronic Acids with Diphenyl Diselenide and Ditelluride
  作者：Lei Wang、Min Wang、Fuping Huang

  DOI：10.1055/s-2005-871936

  日期：——

  In the presence of a catalytic amount of simple copper salt, the reaction of arylboronic acids with diphenyl diselenide and ditelluride was accomplished without any additive to afford the corresponding unsymmetrical diarylselenides and tellurides in good yields.

  在催化量的简单铜盐存在下，芳基硼酸与二苯基二硒化物和二碲化物的反应在没有任何添加剂的情况下完成，以良好的产率得到相应的不对称二芳基硒化物和碲化物。
• Copper-Catalyzed Synthesis of Unsymmetrical Diorganyl Chalcogenides (Te/Se/S) from Boronic Acids under Solvent-Free Conditions
  作者：Sumbal Saba、Giancarlo Botteselle、Marcelo Godoi、Tiago Frizon、Fábio Galetto、Jamal Rafique、Antonio Braga

  DOI：10.3390/molecules22081367

  日期：——

  The efficient and mild copper-catalyzed synthesis of unsymmetrical diorganyl chalcogenides under ligand- and solvent-free conditions is described. The cross-coupling reaction was performed using aryl boric acids and 0.5 equiv. of diorganyl dichalcogenides (Te/Se/S) in the presence of 3 mol % of CuI and 3 equiv. of DMSO, under microwave irradiation. This new protocol allowed the preparation of several

  描述了在无配体和无溶剂条件下有效和温和的铜催化合成不对称二有机基硫属元素化物。使用芳基硼酸和 0.5 当量进行交叉偶联反应。在 3 mol % CuI 和 3 equiv. 存在下二有机基二硫属化物 (Te/Se/S) DMSO，在微波辐射下。这种新方案允许以良好到极好的收率制备几种不对称的二有机基硫属元素化物。
• A general method for the formation of diaryl selenides using copper(I) catalysts
  作者：Rattan K Gujadhur、D Venkataraman

  DOI：10.1016/s0040-4039(02)02480-2

  日期：2003.1

  We report a mild, palladium-free synthetic protocol for the cross coupling reaction of aryl iodides and phenyl selenol using 10 mol% CuI/neocuproine, NaOt-Bu or K2CO3 as base, in toluene, at 110°C. Using this protocol, we show that a variety of diaryl selenides can be synthesized in good yields from commercially available aryl iodides.

  我们报告了一种温和的，不含钯的合成方案，用于在110°C的甲苯中，使用10 mol％CuI /新磷腈，NaO t -Bu或K 2 CO 3作为碱，对芳基碘化物和苯基硒酚进行交叉偶联反应。使用该协议，我们表明可以从商业上可获得的芳基碘化物以高收率合成多种二芳基硒化物。
• Synthesis of Unsymmetrical Diorganyl Chalcogenides under Greener Conditions: Use of an Iodine/DMSO System, Solvent- and Metal-Free Approach
  作者：Sumbal Saba、Jamal Rafique、Antonio L. Braga

  DOI：10.1002/adsc.201500024

  日期：2015.5.4

  Herein, we report a greener iodine‐catalyzed protocol to access different types of unsymmetrical diorganyl chalcogenides. This new approach works in the absence of solvent and metal. The desired products were obtained in good to excellent yields using one equivalent of arylboronic acids, half an equivalent of various diorganyl dichalcogenides, iodine (10 mol%) as a catalyst and 2 equivalents of dimethyl

  本文中，我们报告了一种绿色的碘催化方案，可用于访问不同类型的不对称二有机基硫属元素化物。这种新方法可以在没有溶剂和金属的情况下使用。使用一当量的芳基硼酸，一半当量的各种二有机基二卤代二硫化物，碘（10摩尔％）作为催化剂和2当量的二甲基亚砜（DMSO；作为氧化剂），以良好的产率获得所需的产物。在微波照射下10分钟的时间。
• CuS/Fe: a novel and highly efficient catalyst system for coupling reaction of aryl halides with diaryl diselenides
  作者：Yaming Li、Huifeng Wang、Xiaoying Li、Tao Chen、Defeng Zhao

  DOI：10.1016/j.tet.2010.09.061

  日期：2010.11

  The CuS catalyzed coupling reactions of aryl halides and diaryl diselenides were accelerated by the addition of Fe powder in only 3–12 h with good to excellent yields. SEM–EDX indicated that the in situ iron oxides as support against catalyst agglomeration accelerated the reaction. This catalyst system was also demonstrated recyclable without significant loss of catalytic activity.

  仅在3到12 h内加入铁粉即可加快CuS催化的芳基卤化物和二芳基二硒化物的偶联反应。SEM-EDX表明，原位氧化铁作为载体防止催化剂的团聚加速了反应。还证明了该催化剂体系是可回收的，而没有明显的催化活性损失。