2-(苯磺酰基)-1,3,5-三甲基苯 | 3112-82-1

• 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-(苯磺酰基)-1,3,5-三甲基苯
• 英文名称: (2,4,6-trimethylphenyl) phenyl sulfone
• 英文别名: 1,3,5-trimethyl-2-(phenylsulfonyl)benzene；(2,4,6-trimethylphenyl)-phenyl sulfone；(2,4,6-Trimethylphenyl)phenyl sulfone；(2,4,6-trimethylphenyl)phenylsulfone；2,4,6-trimethylphenyl phenyl sulfone；mesityl phenyl sulfone；2-(benzenesulfonyl)-1,3,5-trimethylbenzene
• CAS: 3112-82-1
• 化学式: C₁₅H₁₆O₂S
• 分子量: 260.357
• InChiKey: KASDQDYPCNMNLM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  42.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(苯磺酰基)-1,3,5-三甲基苯 在 lithium amalgam 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以100%的产率得到均三甲苯
  参考文献：
  名称：

  Horner, Leopold; Schmitt, Rolf-Erhard, Phosphorus and Sulfur and the Related Elements, 1982, vol. 13, p. 301 - 308

  摘要：

  DOI：
• 作为产物：
  描述：

  2,4,6-三甲基二苯硫醚 在 双氧水 、 溶剂黄146 作用下， 生成 2-(苯磺酰基)-1,3,5-三甲基苯
  参考文献：
  名称：

  Leandri et al., Gazzetta Chimica Italiana, 1954, vol. 84, p. 73,82

  摘要：

  DOI：

文献信息

• 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。
• Synthesis of Diaryl Sulfones at Room Temperature: Cu-Catalyzed Cross-Coupling of Arylsulfonyl Chlorides with Arylboronic Acids
  作者：Feng Hu、Xiangyang Lei

  DOI：10.1002/cctc.201500174

  日期：2015.5.18

  An efficient and convenient method for the synthesis of diaryl sulfones was developed through the Cu‐catalyzed cross‐couplings of arylsulfonyl chlorides and arylboronic acids at room temperature in open air. This method is characterized by the use of inexpensive and readily available catalyst and substrates, mild reaction conditions, wide functionality tolerance, short reaction times for most substrates

  通过在室温下露天进行铜催化的芳基磺酰氯和芳基硼酸的交叉偶联反应，开发了一种有效，方便的合成二芳基砜的方法。该方法的特征在于使用廉价且容易获得的催化剂和底物，温和的反应条件，宽泛的功能耐受性，大多数底​​物的反应时间短以及中等至良好的产率。
• A practical synthesis of aryl sulfones via cross-coupling of sulfonyl hydrazides with aryltriazenes using copper/ionic liquid combination
  作者：Anand Kumar Pandey、Saurabh Kumar、Rahul Singh、Krishna Nand Singh

  DOI：10.1016/j.tet.2018.09.059

  日期：2018.11

  A new and efficient approach adopting copper-catalyzed cross-coupling of sulfonyl hydrazides with aryltriazenes has been developed to synthesize aryl sulfones using Brønsted acidic ionic liquid as promoter under ambient conditions. The process employs stable and easy to handle reacting partners, and is endowed with broad substrate scope.

  已开发出一种新的高效方法，该方法采用铜酰肼与磺酰基芳基三嗪的交叉偶联，在环境条件下使用布朗斯台德酸性离子液体作为促进剂来合成芳基砜。该方法使用稳定且易于处理的反应伙伴，并具有广泛的底物范围。
• Metal-Free Synthesis of Diaryl Sulfones from Arylsulfinic Acid Salts and Diaryliodonium Salts
  作者：Natalie Umierski、Georg Manolikakes

  DOI：10.1021/ol303248h

  日期：2013.1.4

  An efficient, high-yielding, and transition-metal-free synthesis of diaryl sulfones from arylsulfinic acid salts and diaryliodonium salts has been developed. The mild reaction conditions tolerate a range of functional groups, and unsymmetrical diaryliodonium salts show high chemoselectivity.

  已经开发了由芳基亚磺酸盐和二芳基碘鎓盐高效，高产率且无过渡金属的二芳基砜的合成方法。温和的反应条件可耐受一系列官能团，并且不对称的二芳基碘鎓盐显示出较高的化学选择性。
• Metal-free, high yielding synthesis of unsymmetrical biaryl, bi(heteroaryl), aryl vinyl, aryl alkyl sulfones via coupling of aryne with sulfinic acid salts
  作者：Sravan Kumar Aithagani、Kushalava Reddy Yempalla、Gurunadham Munagala、Ram A. Vishwakarma、Parvinder Pal Singh

  DOI：10.1039/c4ra07370c

  日期：——

  Here, we report a metal-free, high yielding method for the synthesis of unsymmetrical biaryl sulfones via coupling of aryne with sulfinic acid salts. The optimized condition also works efficiently for bi(heteroaryl), aryl vinyl and aryl alkyl sulfones. The present method took comparatively shorter reaction times and has good functional group compatibility.

  在这里，我们报告了一种无金属的高产率方法，该方法通过亚芳基与亚磺酸盐的偶联来合成不对称联芳基砜。优化的条件对于双（杂芳基），芳基乙烯基和芳基烷基砜也有效。本方法反应时间相对较短，并且具有良好的官能团相容性。

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