(E)-1-methyl-4-(2-(methylsulfonyl)vinyl)benzene | 69957-45-5

• 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-methyl-4-(2-(methylsulfonyl)vinyl)benzene
• 英文别名: 2-(p-Methylphenyl)vinylmethylsulfone；1-methyl-4-[(E)-2-methylsulfonylethenyl]benzene
• CAS: 69957-45-5
• 化学式: C₁₀H₁₂O₂S
• 分子量: 196.27
• InChiKey: FAXBAWDPIWJGMV-BQYQJAHWSA-N

物化性质

• 熔点：
  111 °C
• 沸点：
  381.2±21.0 °C(Predicted)
• 密度：
  1.170±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• 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：

  (E)-1-methyl-4-(2-(methylsulfonyl)vinyl)benzene 在 苯乙酮 作用下， 以 苯 为溶剂， 生成 cis-β-(4-Methyl-styryl)-methyl-sulfon
  参考文献：
  名称：

  Wegener, Wolfgang; Hoffmann, Katrin; Alder, Lutz, Zeitschrift fur Chemie, 1981, vol. 21, # 4, p. 151

  摘要：

  DOI：
• 作为产物：
  描述：

  (E)-2-Methanesulfonyl-3-p-tolyl-acrylic acid ethyl ester 在 lithium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以80%的产率得到(E)-1-methyl-4-(2-(methylsulfonyl)vinyl)benzene
  参考文献：
  名称：

  Preparation of α,β-Unsaturated Sulfones by the Knoevenagel Method

  摘要：

  DOI：

  10.1055/s-1980-29213

文献信息

• Ammonium iodide-induced sulfonylation of alkenes with DMSO and water toward the synthesis of vinyl methyl sulfones
  作者：Xiaofang Gao、Xiaojun Pan、Jian Gao、Huawen Huang、Gaoqing Yuan、Yingwei Li

  DOI：10.1039/c4cc07606k

  日期：——

  A novel ammonium iodide-induced sulfonylation of alkenes with DMSO and water toward the synthesis of vinyl methyl sulfones is described. The process proceeded smoothly under metal-free conditions with high stereoselectivity and good functional group tolerance. The reaction mechanism was revealed to proceed through a domino reaction of oxidation and elimination after the radical addition to alkenes

  描述了一种新型的碘化铵诱导的烯烃与DMSO和水的磺酰化反应，以合成乙烯基甲基砜。该过程在无金属条件下顺利进行，具有高立体选择性和良好的官能团耐受性。在自由基加成到烯烃上之后，揭示了反应机理是通过氧化和消除的多米诺反应进行的。
• Catalytic and direct methyl sulfonylation of alkenes and alkynes using a methyl sulfonyl radical generated from a DMSO, dioxygen and copper system
  作者：Yaojia Jiang、Teck-Peng Loh

  DOI：10.1039/c4sc01901f

  日期：——

  This paper describes an efficient method to β-keto methyl sulfones and (E)-vinyl methyl sulfones using DMSO as the substrate. The methyl sulfonyl radical generated from DMSO in the presence of catalytic Cu(I) under O2 atmosphere is believed to be involved in this reaction. Isotopic labeling and 18O2 experiments were performed to investigate the reaction mechanism.

  本文介绍了一种有效的方法，以DMSO为底物，制备β-酮甲基砜和（E）-乙烯基甲基砜。据信在O 2气氛下在催化性Cu（I）存在下由DMSO产生的甲基磺酰基自由基参与了该反应。进行同位素标记和18 O 2实验以研究反应机理。
• Heck Vinylations Using Vinyl Sulfide, Vinyl Sulfoxide, Vinyl Sulfone, or Vinyl Sulfonate Derivatives and Aryl Bromides Catalyzed by a Palladium Complex Derived from a Tetraphosphine
  作者：Henri Doucet、Maurice Santelli、Ahmed Battace、Touriya Zair

  DOI：10.1055/s-2006-950244

  日期：2006.10

  affords an efficient catalyst for the Heck reaction ofsulfur-containing alkenes with aryl bromides. The rates and yields of the reactions strongly depend on the oxidation state of the sulfur atom. Using vinyl sulfides with 1 mol% catalyst, low to moderate yields of arylated alkenes were obtained. Phenyl vinyl sulfoxide was found to be more reactive, and satisfactory yields of (E)-[2-(phenylsulfinyl)vinyl]benzene

  硫化合物对催化性能的不利影响是众所周知的。四膦cis,cis,cis-1,2,3,4-四[​​(二苯基膦基)甲基]环戊烷与烯丙基氯钯二聚体结合为含硫烯烃与芳基溴化物的Heck反应提供了有效的催化剂。反应的速率和产率很大程度上取决于硫原子的氧化态。使用具有 1 mol% 催化剂的乙烯基硫化物，获得了低至中等收率的芳基化烯烃。发现苯基乙烯基亚砜更具反应性，并且使用 1 mol% 催化剂获得了令人满意的 (E)-[2-(苯基亚磺酰基)乙烯基]苯衍生物产率。使用甲基乙烯基砜，使用 1-0.1 mol% 的催化剂获得了非常高产率的 (E)-[2-(甲基磺酰基)乙烯基]苯衍生物。
• Anion-Functionalized Ionic Liquids Enhance the CuI-Catalyzed Cross-Coupling Reaction of Sulfinic Acid Salts with Aryl Halides and Vinyl Bromides
  作者：Cheng Ma、Ming Bian、Fada Xu

  DOI：10.1055/s-2007-990778

  日期：2007.10

  An easily accessible, anion-functionalized ionic liquid, 1-ethyl-3-methylimidazolium (S)-2-amino-3-methylbutyric acid salt, [emim][Val], has been demonstrated to be an efficient additive for the CuI-catalyzed coupling reaction of sulfinic acid salts with aryl iodides, aryl bromides and vinyl bromides, leading to the formation of sulfones in good yields.

  一种易于获得、阴离子功能化的离子液体，即1-乙基-3-甲基咪唑（S）-2-氨基-3-甲基丁酸盐，[emim][Val]，已被证明是一种高效的添加剂，用于CuI催化的亚磺酸盐与碘苯、溴苯和乙烯基溴的偶联反应，从而以良好的产率形成砜。
• CuSO₄·5H₂O-<i>H</i>-Phosphonate-Catalyzed Intermolecular C-S Bond Formation: Synthesis of (<i>E</i>)-Vinyl Alkylsulfones from Alkynes­ and DMSO
  作者：Jian-Yu Chen、Xiao-Lan Chen、Xu Li、Ling-Bo Qu、Qing Zhang、Li-Kun Duan、Ying-Ya Xia、Xin Chen、Kai Sun、Zhi-Dong Liu、Yu-Fen Zhao

  DOI：10.1002/ejoc.201403278

  日期：2015.1

  A CuSO4·5H2O-H-phosphonate-catalyzed synthesis of (E)-vinyl alkylsulfones from alkynes and widely available DMSO was developed. The present protocol provides an alternative approach to various vinyl sulfones, with the advantages of cheap catalysts, readily available starting materials, operational simplicity and high stereo- and regioselectivity.

  开发了 CuSO4·5H2O-H-膦酸酯催化从炔烃和广泛使用的 DMSO 合成 (E)-乙烯基烷基砜。本协议为各种乙烯基砜提供了一种替代方法，其优点是催化剂便宜、原料易得、操作简单、立体选择性和区域选择性高。