(E)-1-bromo-3-(styrylsulfonyl)benzene | 138147-85-0

• 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: (E)-1-bromo-3-(styrylsulfonyl)benzene
• 英文别名: 1-bromo-3-[(E)-2-phenylethenyl]sulfonylbenzene
• CAS: 138147-85-0
• 化学式: C₁₄H₁₁BrO₂S
• 分子量: 323.21
• InChiKey: FFOHYPYLOSEBRA-MDZDMXLPSA-N

物化性质

• 沸点：
  486.1±45.0 °C(Predicted)
• 密度：
  1.494±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 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：

  m-Bromphenyl-trans-styrylsulfid 在 双氧水 、 溶剂黄146 作用下， 生成 (E)-1-bromo-3-(styrylsulfonyl)benzene
  参考文献：
  名称：

  Baliah,V.; Rathinasamy,T.K., Indian Journal of Chemistry, 1971, vol. 9, p. 220 - 225

  摘要：

  DOI：

文献信息

• Copper-Catalyzed Heck-Type Couplings of Sulfonyl Chlorides with Olefins: Efficient and Rapid Access to Vinyl Sulfones
  作者：Lixia Liu、Pan Xue、Qiulin Chen、Chengming Wang

  DOI：10.1016/j.tetlet.2021.153319

  日期：2021.9

  A copper-catalyzed redox-neutral alkene sulfonylation reaction has been developed. This reported protocol can be easily scale up to a gram scale, and smoothly applied to the late-stage modification of several bioactive molecules.

  已开发出铜催化的氧化还原-中性烯烃磺酰化反应。该报告的协议可以轻松扩展到克级，并顺利应用于几种生物活性分子的后期修饰。
• Silver-Catalyzed Denitrative Sulfonylation of β-Nitrostyrenes: A Conve­nient Approach to (<i>E</i>)-Vinyl Sulfones
  作者：Twinkle Keshari、Ritu Kapoorr、Lal Dhar S. Yadav

  DOI：10.1002/ejoc.201600237

  日期：2016.5

  (readily available by the Henry reaction) for a highly stereoselective, convenient, and catalytic synthesis of (E)-vinyl sulfones at room temperature was investigated. The protocol involves efficient silver-catalyzed denitrative radical cross-coupling of β-nitrostyrenes and sodium sulfinates by using potassium persulfate as an additive to complete the catalytic cycle.

  研究了首次利用 β-硝基苯乙烯（可通过亨利反应获得）在室温下高度立体选择性、方便和催化合成（E）-乙烯基砜。该协议涉及通过使用过硫酸钾作为添加剂来完成催化循环的 β-硝基苯乙烯和亚磺酸钠的有效银催化脱硝自由基交叉偶联。
• Aerobic Copper-Catalyzed Synthesis of (<i>E</i>)-Vinyl Sulfones by Direct C–S Bond Oxidative Coupling
  作者：Xiao Liang、Mingteng Xiong、Heping Zhu、Kexin Shen、Yuanjiang Pan

  DOI：10.1021/acs.joc.9b01400

  日期：2019.9.6

  Copper-catalyzed aerobic oxidative C–S bond coupling reaction between thiophenols and aryl-substituted alkenes for (E)-vinyl sulfones synthesis is reported here. With air utilized as a green oxidant, this transformation not only produces various vinyl sulfones in moderate to good yields but also possesses a simple and ecofriendly system. To clarify the mechanism, kinetic experiments has been investigated

  在此报道了铜催化的硫酚与芳基取代的烯烃之间的需氧氧化C-S键偶联反应，用于合成（E）-乙烯基砜。通过将空气用作绿色氧化剂，这种转化不仅可以以中等到良好的产率生产出各种乙烯基砜，而且还具有简单而环保的体系。为了阐明机理，已经研究了动力学实验。
• Controlled Synthesis of <i>β</i> ‐Keto Sulfones and Vinyl Sulfones under Electrochemical Oxidation
  作者：Yang Fang、Dongping Xu、Yingliang Yu、Rumeng Tang、Shuaishuai Dai、Zhenghua Wang、Wu Zhang

  DOI：10.1002/ejoc.202200091

  日期：2022.4.5

  Selective sulfonylation and oxosulfonylation of alkenes with sulfinates have been developed via anodic oxidation in an undivided cell. The novel electrosynthetic method provided β-keto sulfones and vinyl sulfones with good to excellent yields in the absence of any transition metal catalyst and oxidants. Mechanism studies show that two different pathways involved in these two transformations.

  烯烃与亚磺酸盐的选择性磺酰化和氧代磺酰化已通过在未分裂电池中的阳极氧化进行了开发。在没有任何过渡金属催化剂和氧化剂的情况下，新的电合成方法提供了具有良好至优异产率的 β-酮砜和乙烯基砜。机制研究表明，这两种转化涉及两种不同的途径。
• Metal-free catalyzed synthesis of the (E)-vinyl sulfones via aromatic olefins with arylsulfonyl hydrazides
  作者：Zhenzhen Zhan、Haojie Ma、Daidong Wei、Jinghong Pu、Yixin Zhang、Guosheng Huang

  DOI：10.1016/j.tetlet.2018.02.078

  日期：2018.4

  Synthesis of vinyl sulfones from aromatic olefins and arylsulfonyl hydrazides via I2-TBHP catalyzed system under the N2 atmosphere is described. Owing to no use of metal, only producing N2 and water as the byproducts and directly available reactants, this reaction could validly avoid many disadvantages of the transition metal catalysts. In addition, the desired product can be collected with moderate

  描述了在N 2气氛下经由I 2 -TBHP催化的系统由芳族烯烃和芳基磺酰肼合成乙烯基砜。由于不使用金属，仅产生N 2和水作为副产物和直接可得的反应物，该反应可有效避免过渡金属催化剂的许多缺点。另外，可以在合适的条件下以中等至极好的收率收集期望的产物。