(E)-1-bromo-3-(2-tosylvinyl)benzene | 56759-14-9

• 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-(2-tosylvinyl)benzene
• 英文别名: 1-bromo-3-[(E)-2-(4-methylphenyl)sulfonylethenyl]benzene
• CAS: 56759-14-9
• 化学式: C₁₅H₁₃BrO₂S
• 分子量: 337.237
• InChiKey: QKWHMSKRWCDOCY-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  3-(3-bromophenyl)prop-2-en-1-al 在 碘 、 四氯化钛 、 potassium carbonate 、 溴乙酸乙酯 、 三苯基膦 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 10.0h， 生成 (E)-1-bromo-3-(2-tosylvinyl)benzene
  参考文献：
  名称：

  Iodine-Catalyzed Facile Approach to Sulfones Employing TosMIC as a Sulfonylating Agent

  摘要：

  A novel iodine-catalyzed functionalization of a variety of olefins and alkynes and direct decarboxylative functionalization of cinnamic and propiolic acids with TosMIC to provide access to various vinyl, allyl, and beta-iodo vinylsulfones is described. This simple, efficient, and environmentally benign approach employing inexpensive molecular iodine as a catalyst demonstrates a versatile protocol for the synthesis of highly valuable sulfones, rendering it attractive to both synthetic and medicinal chemistry.

  DOI：

  10.1021/acs.orglett.7b00896

文献信息

• Electrosynthesis of vinyl sulfones from alkenes and sulfonyl hydrazides mediated by KI: Аn electrochemical mechanistic study
  作者：Alexander O. Terent'ev、Olga M. Mulina、Dmitry A. Pirgach、Alexey I. Ilovaisky、Mikhail A. Syroeshkin、Nadezhda I. Kapustina、Gennady I. Nikishin

  DOI：10.1016/j.tet.2017.10.047

  日期：2017.12

  sulfones were prepared from alkenes and sulfonyl hydrazides via electrochemical oxidative sulfonylation. The reaction proceeds in an experimentally convenient undivided electrochemical cell equipped with graphite and iron electrodes employing KI as a redox catalyst and a supporting electrolyte. Applying extremely high current density up to 270 mA/cm2 permits rapid synthesis in a compact reactor and

  由烯烃和磺酰肼通过电化学氧化磺酰化反应制备了各种乙烯基砜。该反应在配备了石墨和铁电极且使用KI作为氧化还原催化剂和支持电解质的实验方便的未分隔电化学电池中进行。施加高达270 mA / cm 2的极高电流密度，可以在紧凑的反应器中以小表面积电极快速合成。利用循环伏安法提出了一种可能的反应机理。在该反应中阳极和阴极过程的结合使得可以在温和的条件下以中等至高的产率获得产物。
• Electrochemical Synthesis of Vinyl Sulfones by Sulfonylation of Styrenes with a Catalytic Amount of Potassium Iodide
  作者：Hui Gao、Pin-Hua Li、Pei-Long Wang、Zhi-Sheng Jiang、Chao Li、Zhi-Ao Tian

  DOI：10.1055/s-0040-1707249

  日期：2020.10

  An electrochemical sulfonylation reaction of styrenes was developed in which sodium arylsulfinates were used as sulfonylating reagents, a catalytic amount of KI was used as a redox mediator, and Bu4NBF4 was used as the electrolyte. In addition to various styrenes, sodium arylsulfinates with either electron-donating or electron-withdrawing groups were tolerated.

  一种苯乙烯的电化学磺化反应被开发出来，其中使用苯基亚砜钠作为磺化试剂，使用催化量的碘化钾作为氧化还原中介体，以及使用Bu4NBF4作为电解质。除了各种苯乙烯外，带有供电子基团或吸电子基团的苯基亚砜钠也能被容忍。
• Revealing the metal-like behavior of iodine: an iodide-catalysed radical oxidative alkenylation
  作者：Shan Tang、Yong Wu、Wenqing Liao、Ruopeng Bai、Chao Liu、Aiwen Lei

  DOI：10.1039/c4cc00644e

  日期：——

  Catalytic HI elimination similar to the β-hydride elimination of transition metals was realized for the radical alkenylation of sulfonyl hydrazides.

  类似于过渡金属的β-氢化物消除反应，对磺酰基肼的自由基烯基化实现了催化HI消除反应。
• Copper-Catalyzed Radical Reaction of <i>N</i>-Tosylhydrazones: Stereoselective Synthesis of (<i>E</i>)-Vinyl Sulfones
  作者：Shuai Mao、Ya-Ru Gao、Xue-Qing Zhu、Dong-Dong Guo、Yong-Qiang Wang

  DOI：10.1021/acs.orglett.5b00461

  日期：2015.4.3

  radical reaction to synthesize vinyl sulfones from readily available N-tosylhydrazones has been described. The protocol provides a novel strategy for the synthesis of various vinyl sulfones including α, β-disubstituted ones and terminal ones. The advantages of the transformation include excellent E stereoselectivity, broad substrate scope, low cost of reagents, and convenient operation. A novel and efficient

  已经描述了肼的新化学反应，该化学反应是铜催化的自由基反应，以从容易获得的N-甲苯磺酰基hydr酮合成乙烯基砜。该方案为合成各种乙烯基砜提供了一种新颖的策略，包括α，β-二取代的和端基的。转化的优点包括出色的E立体选择性，广泛的底物范围，低成本的试剂以及方便的操作。已经实现了由N-甲苯磺酰基hydr酮新颖且有效的一锅法合成炔烃。这些研究为乙烯基砜和炔烃的合成提供了重要的补充方法。
• Synthesis of vinyl sulfones through sulfonylation of styrenes with sulfonyl chlorides under metal-free conditions
  作者：Xia Wang、Bo Hu、Peng Yang、Qian Zhang、Dong Li

  DOI：10.1016/j.tet.2020.131082

  日期：2020.4

  sulfonylation of styrenes with sulfonyl chlorides was developed for the synthesis of vinyl sulfones. The reaction proceeded under metal-free, mild and neutral conditions without extra oxidants or bases. It also exhibited good air and moisture tolerance, broad substrate scope and high chemo-selectivity, affording the vinyl sulfones in moderate to good yields.

  开发了一种高价碘试剂介导的苯乙烯与磺酰氯的磺酰化反应，用于合成乙烯基砜。反应在无金属，温和和中性的条件下进行，没有额外的氧化剂或碱。它还表现出良好的耐空气和湿气性，广泛的底物范围和高的化学选择性，从而以中等至良好的收率提供了乙烯基砜。