(E)-1-methylthio-2-(3-methoxyphenyl)ethene | 89761-21-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-1-methylthio-2-(3-methoxyphenyl)ethene
• 英文别名: (E)-(3-methoxystyryl)(methyl)sulfane；1-methoxy-3-[(E)-2-methylsulfanylethenyl]benzene
• CAS: 89761-21-7
• 化学式: C₁₀H₁₂OS
• 分子量: 180.271
• InChiKey: IJXSCNUOUIAZNW-VOTSOKGWSA-N

物化性质

• 沸点：
  299.4±23.0 °C(Predicted)
• 密度：
  1.070±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.03
• 重原子数：
  12.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (E)-1-methylthio-2-(3-methoxyphenyl)ethene 反应 22.0h， 以33%的产率得到(E)-(S)-(+)-methyl-<2-phen-(3'methoxy)-yl> vinyl sulfoxide
  参考文献：
  名称：

  Microbiological and chemical methods in the asymmetric oxidation of sulfides: A comparative study for the preparation of (S)-vinyl sulfoxides

  摘要：

  The enantiogenicity of biological and chemical oxidation at the sulfur atom was studied on a series of prochiral vinyl sulfides for the preparation of sulfoxides of (S)-absolute configuration. Using either fungal cultures, Sharpless-modified reagent or chiral oxaziridine, the enantiomeric excesses varied according to the substrate's steric and/or electronic structure; the three methods were complementary.

  DOI：

  10.1016/s0957-4166(00)82296-x
• 作为产物：
  描述：

  (E)-1-methylsulfinyl-1-methylthio-2-(3-methoxyphenyl)ethene 在 四丁基碘化铵 、 苯酚 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以78%的产率得到(E)-1-methylthio-2-(3-methoxyphenyl)ethene
  参考文献：
  名称：

  非水介质中汞电极电解还原 1-Methylsulfinyl-1-methylthio-1-烯烃

  摘要：

  在电解还原通式有机硫化合物时（注：图略），R=芳基的底物比R=烷基的底物更容易还原，前者得到脱亚磺酰化的化合物，E-异构体RCH=CH(SMe)，产率良好，但后面的底物不会产生相应的脱亚磺酰化合物。

  DOI：

  10.1246/bcsj.59.2009

文献信息

• ELECTROLYTIC REDUCTION OF 1-METHYLSULFINYL-1-METYLTHIO-2-ARYLETHENES AT MERCURY AND PLATINUM ELECTRODES IN ACETONITRIL
  作者：Akira Kunugi、Kyo Abe

  DOI：10.1246/cl.1984.159

  日期：1984.2.5

  The electrolytic reduction of 1-methylsulfinyl-1-methylthio-2-arylethenes involves a cleavage of one carbon–sulfur bond, resulting in formation of E-1-methylthio-2-arylethenes in good yields, but not Z-isomers, in the presence of excess phenol as a proton donor.

  1-甲基亚磺酰基-1-甲硫基-2-芳基乙烯的电解还原涉及一个碳-硫键的断裂，导致以良好的产率形成E-1-甲硫基-2-芳基乙烯，但不形成Z-异构体。存在过量的苯酚作为质子供体。
• Zincation of Styrylsulfonium Salts
  作者：Kodai Yamada、Mika B. Kintzel、Gregory J. P. Perry、Hayate Saito、Hideki Yorimitsu

  DOI：10.1021/acs.orglett.2c03013

  日期：2022.10.14

  We report the formation of zinc reagents by the reaction of styrylsulfonium salts with zinc powder. Transition metals and other additives are not required for promoting zincation. Zincation tolerates a variety of sensitive functional groups, including esters, bromides, and boronic esters, and proceeds with complete retention of stereochemistry. This method presents a practical approach to the formation

  我们报道了通过苯乙烯基锍盐与锌粉反应形成锌试剂。不需要过渡金属和其他添加剂来促进锌化。锌化可耐受多种敏感官能团，包括酯、溴化物和硼酸酯，并完全保留立体化学。该方法提供了一种形成锌试剂的实用方法，可用于各种官能化，例如卤化、羧化和根岸交叉偶联。
• Microbiological and chemical methods in the asymmetric oxidation of sulfides: A comparative study for the preparation of (S)-vinyl sulfoxides
  作者：Claude Rossi、Annie Fauve、Michel Madesclaire、Danielle Roche、Franklin A. Davis、R. Thimma Reddy

  DOI：10.1016/s0957-4166(00)82296-x

  日期：1992.5

  The enantiogenicity of biological and chemical oxidation at the sulfur atom was studied on a series of prochiral vinyl sulfides for the preparation of sulfoxides of (S)-absolute configuration. Using either fungal cultures, Sharpless-modified reagent or chiral oxaziridine, the enantiomeric excesses varied according to the substrate's steric and/or electronic structure; the three methods were complementary.
• Electrolytic Reduction of 1-Methylsulfinyl-1-methylthio-1-alkenes at Mercury Electrode in Nonaqueous Media
  作者：Akira Kunugi、Kyo Abe、Toshio Hagi、Taketsugu Hirai

  DOI：10.1246/bcsj.59.2009

  日期：1986.6

  In the electrolytic reduction of organic sulfur compounds of general formular (Remark: Graphics omitted.), the substrates with R=aryl are much easier to reduce than those with R=alkyl, and the former substrates afford the desulfinylated compounds, E-isomers of RCH=CH(SMe), in good yields, but the later substrates do not give the corresponding desulfinylated compounds.

  在电解还原通式有机硫化合物时（注：图略），R=芳基的底物比R=烷基的底物更容易还原，前者得到脱亚磺酰化的化合物，E-异构体RCH=CH(SMe)，产率良好，但后面的底物不会产生相应的脱亚磺酰化合物。