乙烯基亚磺酰甲基苯 | 73927-19-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 乙烯基亚磺酰甲基苯
• 英文名称: benzyl vinyl sulfoxide
• 英文别名: Benzylvinylsulfoxide；ethenylsulfinylmethylbenzene
• CAS: 73927-19-2
• 化学式: C₉H₁₀OS
• 分子量: 166.244
• InChiKey: SMWJPJLZIVEXKQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  36.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙烯基亚磺酰甲基苯 在 对甲苯磺酸 、 对苯二酚 作用下， 以 xylene 为溶剂， 反应 13.0h， 生成 hexahydro-2-phenyl-4,6-methanocyclopent[e]-1,3-oxathiin
  参考文献：
  名称：

  Construction of 1,3-Oxathiane Ring through Pummerer Reaction of .GAMMA.,.DELTA.-Unsaturated Sulfinyl Compounds.

  摘要：

  制备了几种γ,δ-不饱和亚磺酰化合物，并考察了它们与对甲苯磺酸的反应。构象刚性的γ,δ-不饱和亚磺酰化合物，如内向(烷基亚磺酰基)降冰片烯或1-(烷基亚磺酰基)-2-异丙烯基苯衍生物，通过分子内Pummerer重排反应生成1,3-氧硫杂环烷。

  DOI：

  10.1248/cpb.45.778
• 作为产物：
  描述：

  乙烯基硫烷基甲基苯 生成 乙烯基亚磺酰甲基苯
  参考文献：
  名称：

  Annunziata,R.; Cinquini,M., Journal of the Chemical Society. Perkin transactions I, 1979, p. 1684 - 1686

  摘要：

  DOI：

文献信息

• The selective generation of trans-substituted lithium and sodium ethenesulfenate anions
  作者：Adrian L. Schwan、Mark F. Pippert、Hung H. Pham、Michael R. Roche

  DOI：10.1039/c39930001312

  日期：——

  The reaction of anti-alkyl thiirane S-oxides 1 with hindered amide bases affords trans-substituted ethenesulfenate anions viaa deprotonation–ring-opening sequence.

  抗烷基硫杂环丁烷S-氧化物1与受阻酰胺碱的反应通过去质子化-开环序列提供了反式取代的乙磺酸根阴离子。
• Theoretical and Experimental Analyses of the Deprotonation of Thiirane S-Oxides: The Stereoselective Formation of trans-Alkyl- and gem-Silylethenesulfenate Anions
  作者：Mitchell D. Refvik、Robert D. J. Froese、John D. Goddard、Hung H. Pham、Mark F. Pippert、Adrian L. Schwan

  DOI：10.1021/ja00106a022

  日期：1995.1

  Experimental and theoretical studies of the regioselective deprotonation of thiirane S-oxides are reported. Experimentally under the reaction conditions of LiHMDS/THF/-78 degrees C with anti-alkylthiirane S-oxides or anti-silylthiirane S-oxides as starting materials, the products of ring-opening are (E)-2-alkylethenesulfenate and 1-silylethenesulfenate anions, respectively. Experiments involving deuterium labeling clearly indicate that a regioselective deprotonation reaction was followed by a stereoselective ring-opening. Ab initio methods at both the Hartree-Fock and Moller-Plesset perturbation theory levels with the 6-31+G(d) basis set were used to examine both lithiated methyl- and silylthiirane S-oxides. Of the possible anti-substituted species, the coordination of the lithium anti to the methyl and gem to the silyl is predicted to be the most stable. These stable intermediates with the lithium syn to the sulfoxide could ring-open to yield the experimentally observed products.
• Hydrogenative Kinetic Resolution of Vinyl Sulfoxides
  作者：Joan R. Lao、Héctor Fernández-Pérez、Anton Vidal-Ferran

  DOI：10.1021/acs.orglett.5b02139

  日期：2015.8.21

  Enantiopure sulfoxides are valuable precursors of organosulfur compounds with broad application in organic and pharmaceutical chemistry. An unprecedented strategy for obtaining highly enantioenriched sulfoxides based on a hydrogenative kinetic resolution using Rh-complexes of phosphine-phosphite ligands as catalysts is reported. After optimization, highly efficient conditions for the kinetic resolution of racemic sulfoxides have been identified. This methodology has been applied to a set of racemic aralkyl or aryl vinyl sulfoxides and allowed the isolation of both recovered and reduced products in excellent yields and enantioselectivities (up to 99% and 97% ee, respectively; 16 examples).
• Schwan, Adrian L.; Roche, Michael R.; Gallagher, John F., Canadian Journal of Chemistry, 1994, vol. 72, # 2, p. 312 - 324
  作者：Schwan, Adrian L.、Roche, Michael R.、Gallagher, John F.、Ferguson, George

  DOI：——

  日期：——
• The one-pot generation and ring opening of alkyl and aryl thiirane-S-oxides
  作者：Adrian L. Schwan、David A. Wilson

  DOI：10.1016/s0040-4039(00)61083-3

  日期：1992.9

  Base induced dehydrochlorination of acyclic alpha-chlorosulfoxides affords thiirane-S-oxides which react further under the alkaline reaction conditions.