1-bromo-4-(4-tolylsulfonylmethyl)benzene | 26885-97-2

• 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-bromo-4-(4-tolylsulfonylmethyl)benzene
• 英文别名: 1-bromo-4-(p-tolylsulfonylmethyl)benzene；4-bromobenzyl 4-methylphenyl sulfone；1-bromo-4-(tosylmethyl)benzene；(4-bromo-benzyl)-p-tolyl sulfone；(4-Brom-benzyl)-p-tolyl-sulfon；p-Brombenzyl-p-Tolylsulfon；1-Bromo-4-{[(4-methylphenyl)sulfonyl]methyl}benzene；1-[(4-bromophenyl)methylsulfonyl]-4-methylbenzene
• CAS: 26885-97-2
• 化学式: C₁₄H₁₃BrO₂S
• 分子量: 325.226
• InChiKey: CQIBZBQBIIUBEK-UHFFFAOYSA-N

物化性质

• 熔点：
  171-172 °C
• 沸点：
  479.5±45.0 °C(Predicted)
• 密度：
  1.449±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  18
• 可旋转键数：
  3
• 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

• 作为反应物：
  描述：

  1-bromo-4-(4-tolylsulfonylmethyl)benzene 在 di-μ-chlorobis{(acetophenone oxime)palladium(II)} 、 potassium carbonate 、 magnesium 、 mercury dichloride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 66.0h， 生成 4-联苯乙酸
  参考文献：
  名称：

  Synthetic Applications of o- and p-Halobenzyl Sulfones as Zwitterionic Synthons:  Preparation of Ortho-Substituted Cinnamates and Biarylacetic Acids

  摘要：

  The synthetic applications of o-halobenzyl and p-halobenzyl sulfones as precursors of 1,3- and 1,5-zwitterionic synthons, respectively, are described. Their alpha-sulfonyl carbanions, generated by means of the phosphazene base P-2-Et or BuLi or K2CO3 under PTC conditions, reacted with different electrophiles such as alkyl halides, aldehydes, and electrophilic olefins. Palladium-catalyzed cross-coupling processes such as Heck, Suzuki, and Sonogashira reactions can be efficiently performed at the halogen atom. These two sequential functionalization processes are applied to the synthesis of ortho-substituted cinnamates and pharmaceuticals belonging to the family of p-biarylacetic acids such as 4-biphenylacetic acid, namoxyrate, xenyhexenic acid, and bipherylpropionic acid.

  DOI：

  10.1021/jo025620s
• 作为产物：
  描述：

  potassium thiotosylate 在 六乙基亚磷酸胺 作用下， 以 乙醚 为溶剂， 生成 1-bromo-4-(4-tolylsulfonylmethyl)benzene
  参考文献：
  名称：

  Organic sulfur chemistry. IX. Chemistry of thiolsulfonates and related derivatives. Nucleophilic reactions on sulfenyl sulfur

  摘要：

  DOI：

  10.1021/jo00801a017

文献信息

• Silver-Catalyzed C(sp3)-H Sulfonylation for the Synthesis of Benzyl Sulfones Using Toluene Derivatives and α-Amino Acid Sulfonamides
  作者：Kyalo Stephen Kanyiva、Kanako Uchida、Takanori Shibata

  DOI：10.1246/bcsj.20200393

  日期：2021.4.15

  We describe a simple and practical protocol for the synthesis of benzyl sulfones using readily available toluene derivatives and α-amino acid sulfonamides. The reaction proceeds to afford a broad range of benzyl sulfones in moderate to high yields under silver catalysis. The mechanism possibly involves a Minisci-type formation of α-aminoalkyl radical, homolytic cleavage of a N-S bond to generate a

  我们描述了一种简单实用的方案，用于使用容易获得的甲苯衍生物和α-氨基酸磺酰胺合成苄基砜。在银催化下，反应进行以中等至高收率提供了广泛范围的苄基砜。该机理可能涉及α-氨基烷基基团的Minisci型形成，NS键的均相裂解以产生磺酰基基团，以及磺酰基基团与经由硫酸根阴离子自由基的氢提取形成的苄基基团偶联。该反应的实用性通过抗癌活性化合物的克级合成和一步合成来证明。研究的机理是通过使用自由基清除剂和氘代甲苯进行的。
• Application of the polyacrylonitrile fiber as a support for the green heterogeneous base catalyst and supported phase-transfer catalyst
  作者：Xian-Lei Shi、Minli Tao、Huikun Lin、Wenqin Zhang

  DOI：10.1039/c4ra12069h

  日期：——

  Highly efficient and recyclable polyethylene polyamine functionalized polyacrylonitrile fiber as the heterogeneous base catalyst and supported phase-transfer catalyst.

  高度高效且可回收的聚乙烯聚胺官能化聚丙烯腈纤维作为异质基催化剂和支撑的相转移催化剂。
• A Protocol To Transform Sulfones into Nitrones and Aldehydes
  作者：Eduardo Rodrigo、Inés Alonso、M. Belén Cid

  DOI：10.1021/acs.orglett.8b02483

  日期：2018.9.21

  A simple method to transform sulfones into nitrones and therefore into the corresponding carbonyl derivatives has been developed. Some examples demonstrate that it is a new reliable and versatile reaction in the toolbox of sulfones that has great synthetic potential. NMR and computational studies were used to elucidate the mechanism.

  已经开发了一种将砜转化为硝酮并因此转化为相应的羰基衍生物的简单方法。一些例子表明，这是砜工具箱中一种可靠且用途广泛的新型反应，具有巨大的合成潜力。核磁共振和计算研究用于阐明机理。
• Selective Oxidation of Sulfides to Sulfoxides and Sulfones Using<b><i>n</i></b>-Butyltriphenylphosphonium Dichromate (Bu^<i>n</i>PPh₃)₂Cr₂O₇in the Presence of Aluminium Chloride in Solution and Under Microwave Irradiation
  作者：Iraj Mohammadpoor-Baltork、Hamid Reza Memarian、Kiumars Bahrami、Karim Esmayilpour

  DOI：10.1080/104265090968091

  日期：2005.12

  sulfones in excellent yields using n-butyltriphenylphosphonium dichromate (BTPPDC) in the presence of aluminium chloride in acetonitrile solution and under microwave irradiation. In addition, selective oxidation of sulfides in the presence of functional groups such as a carbon–carbon double bond, ketone, oxime, aldehyde, ether, and acetal can be considered as a noteworthy advantage of this method.

  使用正丁基三苯基重铬酸鏻 (BTPPDC) 在乙腈溶液中的氯化铝存在下并在微波辐射下，可以将多种硫化物有效氧化为相应的亚砜和砜，产率极好。此外，在碳-碳双键、酮、肟、醛、醚和缩醛等官能团存在下选择性氧化硫化物可被认为是该方法的显着优势。
• Synthesis, spectra (FT-IR, NMR) investigations, DFT, FMO, MEP, NBO analysis and catalytic activity of MoO2(VI) complex with ONO tridentate hydrazone Schiff base ligand
  作者：Hadi Kargar、Mehdi Fallah-Mehrjardi、Reza Behjatmanesh-Ardakani、Khurram Shahzad Munawar

  DOI：10.1016/j.molstruc.2021.131259

  日期：2021.12

  dioxomolybdenum(VI) complex has been successfully prepared by the reaction of an ONO donor Schiff base, derived by condensing 4-amino-2-hydroxybenzohydrazide and 3-ethoxysalicylaldehyde, with MoO2(acac)2. The structures of synthesized products were explored spectroscopically through FT-IR, 1H & 13C NMR and by elemental composition (CHN) through combustion analysis. The tridentate Schiff base ligand is bonded

  一种新的二氧钼 (VI) 配合物已通过 ONO 供体席夫碱的反应成功制备，席夫碱是由 4-氨基-2-羟基苯甲酰肼和 3-乙氧基水杨醛与 MoO 2 (acac) 2缩合得到的。合成产物的结构通过 FT-IR, 1 H & 13C NMR 和通过燃烧分析的元素组成 (CHN)。三齿席夫碱配体通过其去质子化的烯醇和酚氧原子以及偶氮甲碱基团的氮与中心金属键合。通过衍射分析获得的数据的解释验证了制备的金属配合物的扭曲八面体几何形状。此外，探索了钼配合物的催化潜力，用于在乙醇中 30% 的 H 2 O 2水溶液存在下将芳基和烷基硫化物选择性氧化成相应的砜。目前催化工作的主要优势是反应时间短、产率高、后处理简单。