(Z)-α-(methylthio)styryl methyl sulfoxide | 35453-10-2

• 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: (Z)-α-(methylthio)styryl methyl sulfoxide
• 英文别名: [(Z)-2-methylsulfanyl-2-methylsulfinylethenyl]benzene
• CAS: 35453-10-2
• 化学式: C₁₀H₁₂OS₂
• 分子量: 212.337
• InChiKey: IGGPZGRBJMMXBV-NTMALXAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-α-(methylthio)styryl methyl sulfoxide 在 三甲基氯硅烷 、 magnesium 、 苯酚 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以19%的产率得到(E)-β-(methylthio)styrene
  参考文献：
  名称：

  β-芳基乙烯基砜衍生物的镁促进立体选择性脱磺化

  摘要：

  β-芳基乙烯基对甲苯砜很容易通过芳香醛与各种对甲苯砜的碱催化缩合制备，通过镁促进的还原以立体选择性的方式有效地转化为相应的（E）-β-取代的芳香烯烃。该反应可以通过从金属镁到乙烯基砜的电子转移引发，得到相应的阴离子物质，然后立体选择性地消除磺酰基。

  DOI：

  10.1246/cl.2002.478
• 作为产物：
  描述：

  methyl[(E)-1-(methylsulfinyl)-2-phenylvinyl]sulfane 以65%的产率得到
  参考文献：
  名称：

  OGURA, KATSUYUKI;ARAI, KAZUTAKA;TSUCHIHASHI, GEN-ICHI, BULL. CHEM. SOC. JAP., 1982, 55, N 11, 3669-3670

  摘要：

  DOI：

文献信息

• Two-Step, Practical, and Diversity-Oriented Synthesis of Multisubstituted Benzofurans from Phenols through Pummerer Annulation Followed by Cross-coupling
  作者：Kei Murakami、Hideki Yorimitsu、Atsuhiro Osuka

  DOI：10.1246/bcsj.20140241

  日期：2014.12.15

  Practical and diversity-oriented synthesis of multisubstituted benzofurans has been accomplished from simple phenols through a Pummerer annulation/cross-coupling sequence. Operationally simple and rapid reactions of phenols with ketene dithioacetal monoxides (KDMs) with the aid of trifluoroacetic anhydride provide the corresponding 2-methylsulfanylbenzo[b]furans. The scope of the reaction encompasses phenols and KDMs having a broad range of substituents. The remaining methylsulfanyl group in the annulation products is converted to various aryl groups through cross-coupling reactions that we improved specially to this end. This two-step approach to multisubstituted benzofurans is powerful enough to synthesize highly fluorescent benzofuran derivatives as well as the naturally occurring Eupomatenoid family.

  已成功实现从简单酚类化合物合成多取代苯并呋喃的实用且多样化的合成方法，采用了Pummerer环化/交叉偶联序列。酚类与酮硫酰单氧化物（KDMs）在三氟乙酸酐的帮助下发生操作简便、迅速的反应，生成相应的2-甲基硫苯并[b]呋喃。该反应的适用范围涵盖了具有广泛取代基的酚类和KDMs。环化产物中的剩余甲基硫基团通过我们特别改进的交叉偶联反应转化为各种芳基。此两步法合成多取代苯并呋喃的能力足以合成高度荧光的苯并呋喃衍生物，以及天然存在的Eupomatenoid家族。
• Highly Chemoselective Oxidation of Dithioester Enethiolates to Sulfenates:  Application to the Synthesis of Ketene Dithioacetal <i>S</i>-Oxides
  作者：Franck Sandrinelli、Gaëlle Fontaine、Stéphane Perrio、Pierre Beslin

  DOI：10.1021/jo0492362

  日期：2004.10.1

  Enethiolates derived from dithioesters were efficiently converted into the corresponding vinyl sulfenates by oxidation with a unique N-sulfonyloxaziridine la derived from pinacolone. Subsequent alkylation with alkyl halides led to ketene dithioacetal S-oxides in good to excellent yields.
• OGURA K.; ITO Y.; TSUCHIHASHI G., BULL. CHEM. SOC. JAP., 1979, 52, NO 7, 2013-2022
  作者：OGURA K.、 ITO Y.、 TSUCHIHASHI G.

  DOI：——

  日期：——
• Mg-Promoted Stereoselective Desulfonation of β-Arylvinyl Sulfone Derivatives
  作者：Ikuzo Nishiguchi、Takeshi Matsumoto、Takeshi Kuwahara、Makoto Kyoda、Hirofumi Maekawa

  DOI：10.1246/cl.2002.478

  日期：2002.4

  p-tolylsulfones, easily prepared from base-catalyzed condensation of aromatic aldehydes with a variety of p-tolylsulfones, were efficiently transformed to the corresponding (E)-β-substituted aromatic olefins in a stereoselective manner through Mg-promoted reduction. The reaction may be initiated through electron transfer from Mg metal to the vinyl sulfones to give the corresponding anionic species

  β-芳基乙烯基对甲苯砜很容易通过芳香醛与各种对甲苯砜的碱催化缩合制备，通过镁促进的还原以立体选择性的方式有效地转化为相应的（E）-β-取代的芳香烯烃。该反应可以通过从金属镁到乙烯基砜的电子转移引发，得到相应的阴离子物质，然后立体选择性地消除磺酰基。
• OGURA, KATSUYUKI;ARAI, KAZUTAKA;TSUCHIHASHI, GEN-ICHI, BULL. CHEM. SOC. JAP., 1982, 55, N 11, 3669-3670
  作者：OGURA, KATSUYUKI、ARAI, KAZUTAKA、TSUCHIHASHI, GEN-ICHI

  DOI：——

  日期：——