1-methyl-3-tosylbenzene | 53046-20-1

• 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: 1-methyl-3-tosylbenzene
• 英文别名: m-methylphenyl p-tolyl sulfone；1-Methyl-3-(4-methylbenzene-1-sulfonyl)benzene；1-methyl-3-(4-methylphenyl)sulfonylbenzene
• CAS: 53046-20-1
• 化学式: C₁₄H₁₄O₂S
• 分子量: 246.33
• InChiKey: CVVSKVPTZYSPSY-UHFFFAOYSA-N

物化性质

• 熔点：
  102-103 °C
• 沸点：
  408.2±34.0 °C(Predicted)
• 密度：
  1.171±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  3-methyl-2-phenylseleno-1-(p-toluenesulfonyl)-1,4-cyclohexadiene 在 MeCu(SePh)Li 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以78%的产率得到1-methyl-3-tosylbenzene
  参考文献：
  名称：

  Cycloaddition Reactions of 1-Phenylseleno-2-(p-toluenesulfonyl)ethyne

  摘要：

  1-Phenylseleno-2-(p-toluenesulfonyl)ethyne (1) is an effective dienophile and dipolarophile. It underwent facile Diels-Alder reactions with a variety of dienes to afford vicinal sulfone- and selenide-functionalized 1,4-cyclohexadienes. Unexpected regiochemistry that is the opposite of what is obtained with simple acetylenic sulfones was observed with several unsymmetrical dienes containing methyl or methoxy substituents at the 1- or 2-position. Acetylene 1 reacted with (trimethylsilyl)methyl azide, diazomethane, and 2,4,6-trimethylbenzonitrile N-oxide via 1,3-dipolar cycloadditions to afford the corresponding triazole, 1,2-diazole, and isoxazole products. It also underwent an ene reaction with beta-pinene that showed anomalous regiochemistry compared to other acetylenic sulfones. The Diels-Alder cycloadducts obtained from the reaction of 1 with 2,3-dimethyl-1,3,butadiene and 1,3-cyclohexadiene were readily converted into the corresponding beta-keto sulfones and ketones, thus rendering 1 as the synthetic equivalent of p-toluenesulfonylketene and ketene, respectively. Base-catalyzed elimination of TsOH from the Diels-Alder cycloadduct obtained with 2,3-dimethyl-1,3-butadiene afforded the corresponding aryl phenyl selenide, while the adduct from piperylene underwent oxidation to its selenoxide, followed by a Pummerer-type reaction to produce 2-(phenylseleno)-3-(p-toluenesulfonyl)toluene. The reaction of the bicyclic Diels-Alder product obtained from 1,3-cyclohexadiene with MeCu(SePh)Li resulted in substitution of the phenylseleno moiety by a methyl group, whereas similar treatment, of the monocyclic adduct derived from piperylene effected elimination of PhSeH and aromatization.

  DOI：

  10.1021/jo990730t

文献信息

• 一种醋酸钯催化制备二苯基砜类化合物的方 法
  申请人：浙江农林大学暨阳学院

  公开号：CN109824558B

  公开（公告）日：2020-10-09

  本发明公开了一种醋酸钯催化制备式（Ⅲ）所示的二苯基砜类化合物的方法，制备方法为：式（Ⅰ）所示的溴代苯类化合物、硫酸钠和式（Ⅱ）所示的苯甲酸类化合物在二甲基甲酰胺（DMF）为溶剂的反应介质中，在醋酸钯作为催化剂、碱金属碳酸盐作为碱的作用下充分反应，制得反应物，反应物通过后处理制得二苯基砜类化合物；催化剂为20 mol%当量的醋酸钯，碱金属碳酸盐为碳酸铯；反应式中R1选自下列之一：氢、甲基；R2选自下列之一：氢、甲基、甲氧基、三氟甲氧基；本发明原料简便易得，制备条件温和；成本低，对设备的要求较低；后处理方便；催化体系适应性广，适用于大规模工业化生产。
• Method for acylation or sulphonylation of an aromatic compound
  申请人：Rhodia Chimie

  公开号：US06348631B1

  公开（公告）日：2002-02-19

  The present invention relates to a process for the acylation or sulphonylation of an aromatic compound. More particularly, the invention relates to a process for the acylation or sulphonylation of an activated or deactivated aromatic compound. The invention is applied to the preparation of aromatic ketones or sulphones. The process for the acylation or sulphonylation of an aromatic compound which consists in reacting at least one aromatic compound with an acylating or sulphonylating agent, in the presence of a Friedel-Crafts catalyst is characterized in that the acylation or sulphonylation reaction is carried out in liquid phase under microwave irradiation.

  本发明涉及一种芳香化合物的酰化或磺化过程。 更具体地，该发明涉及一种对活化或去活化的芳香化合物进行酰化或磺化的过程。 该发明应用于芳香酮或磺酮的制备。 将至少一种芳香化合物与酰化剂或磺化剂在弗里德尔-克拉夫茨催化剂存在下反应的芳香化合物酰化或磺化过程的特征在于，在微波辐射下在液相中进行酰化或磺化反应。
• Copper-mediated sulfonylation of aryl iodides and bromides with arylsulfonyl hydrazides in PEG-400
  作者：Xiangmei Wu、Yan Wang

  DOI：10.1039/c8nj00075a

  日期：——

  Sulfonylation using stable and readily available arylsulfonyl hydrazides and aryl iodides or bromides mediated by cupric acetate has been achieved. Using polyethylene glycol (PEG-400) as an eco-friendly medium, the coupling reaction could afford a series of unsymmetrical diaryl sulfones in moderate to good yields without the presence of additional ligands and base.

  已经实现了使用稳定且容易获得的芳基磺酰基酰肼和由乙酸铜介导的芳基碘化物或溴化物进行的磺酰化。使用聚乙二醇（PEG-400）作为生态友好型介质，偶联反应可以以中等至良好的收率得到一系列不对称的二芳基砜，而无需其他配体和碱的存在。
• An efficient method for aromatic Friedel–Crafts alkylation, acylation, benzoylation, and sulfonylation reactions
  作者：Ravi P Singh、Rajesh M Kamble、Kusum L Chandra、P Saravanan、Vinod K Singh

  DOI：10.1016/s0040-4020(00)01005-x

  日期：2001.1

  Aromatic electrophilic substitution reactions such as alkylation, acylation, benzoylation, and sulfonylation were studied in the presence of a catalytic amount of Cu(OTf)2 and Sn(OTf)2. Cu(OTf)2 was very efficient for alkylation, acylation, and benzoylation reactions. However, in case of sulfonylation reactions, Sn(OTf)2 gave better results.

  在催化量的Cu（OTf）2和Sn（OTf）2存在下，研究了烷基化，酰化，苯甲酰化和磺酰化等芳香亲电取代反应。Cu（OTf）2对于烷基化，酰化和苯甲酰化反应非常有效。然而，在磺酰化反应的情况下，Sn（OTf）2给出了更好的结果。
• Heterogeneous copper-catalyzed synthesis of diaryl sulfones
  作者：Xinchi Gong、Zhengqi Shen、Ganghu Wang、Lingling Qu、Chunyin Zhu

  DOI：10.1039/d1ob01830b

  日期：——

  A carbon-supported copper nanoparticle (Cu-NP) with high catalytic activity for the synthesis of diaryl sulfones is reported. For the first time, this Cu-NP is proved to be able to effectively promote the reaction of arylboronic acids and arylsulfonyl hydrazides to generate diaryl sulfones at room temperature. The reaction shows excellent substrate universality, and substrates with different substituents

  报道了一种用于合成二芳基砜的具有高催化活性的碳负载铜纳米粒子（Cu-NP）。首次证明该Cu-NP能够有效促进芳基硼酸和芳基磺酰肼在室温下生成二芳基砜的反应。该反应具有优异的底物普适性，不同取代基的底物均能顺利进行反应，以良好的收率得到所需产物。基于XRD，发现Cu-NP由低价Cu制成。因此，据信由 Cu-NP 催化的反应涉及 Cu 介导的有机金属循环。