(E)-(2-(methylsulfonyl)prop-1-en-yl)benzene

• 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)-(2-(methylsulfonyl)prop-1-en-yl)benzene
• 英文别名: Benzene, [2-(methylsulfonyl)-1-propenyl]-；[(E)-2-methylsulfonylprop-1-enyl]benzene
• 化学式: C₁₀H₁₂O₂S
• 分子量: 196.27
• InChiKey: BQIKBTDLRYLUAP-CMDGGOBGSA-N

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)-(2-(methylsulfonyl)prop-1-en-yl)benzene 、 N-溴代丁二酰亚胺(NBS) 以54%的产率得到
  参考文献：
  名称：

  DOOMES E.; OVERTON B. M., J. ORG. CHEM., 52,(1987) N 8, 1544-1548

  摘要：

  DOI：
• 作为产物：
  描述：

  丙-1,2-二烯基苯 、 sodium methansulfinate 在 溶剂红 43 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以82%的产率得到(E)-(2-(methylsulfonyl)prop-1-en-yl)benzene
  参考文献：
  名称：

  Photoredox-Catalyzed Hydrosulfonylation of Arylallenes

  摘要：

  (Het)Arylallenes undergo hydrosulfonylation under photoredox-catalyzed conditions. The reaction gives vinyl sulfones in a regio- and diastereoselective manner, employing sodium sulfinates as the sulfonyl source and eosin Y as the photocatalyst. Indol-1-yl, pyrrol-1-yl, phenyl, and naphtylallenes might be used. Aliphatic allenes are incompatible with the reaction conditions.

  DOI：

  10.1021/acs.joc.9b02960

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。
• 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。
• DOOMES E.; OVERTON B. M., J. ORG. CHEM., 52,(1987) N 8, 1544-1548
  作者：DOOMES E.、 OVERTON B. M.

  DOI：——

  日期：——
• Photoredox-Catalyzed Hydrosulfonylation of Arylallenes
  作者：Olga A. Storozhenko、Alexey A. Festa、Galina I. Detistova、Victor B. Rybakov、Alexey V. Varlamov、Erik V. Van der Eycken、Leonid G. Voskressensky

  DOI：10.1021/acs.joc.9b02960

  日期：2020.2.21

  (Het)Arylallenes undergo hydrosulfonylation under photoredox-catalyzed conditions. The reaction gives vinyl sulfones in a regio- and diastereoselective manner, employing sodium sulfinates as the sulfonyl source and eosin Y as the photocatalyst. Indol-1-yl, pyrrol-1-yl, phenyl, and naphtylallenes might be used. Aliphatic allenes are incompatible with the reaction conditions.