2-hydroxyethyl p-tolyl sulfoxide | 87943-26-8

• 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: 2-hydroxyethyl p-tolyl sulfoxide
• 英文别名: 2-(toluene-4-sulfinyl)-ethanol；(β-Oxy-aethyl)-p-tolyl-sulfoxyd；2-(Toluol-4-sulfinyl)-aethanol；Ethanol, 2-[(4-methylphenyl)sulfinyl]-；2-(4-methylphenyl)sulfinylethanol
• CAS: 87943-26-8
• 化学式: C₉H₁₂O₂S
• 分子量: 184.259
• InChiKey: SLYNYMYUQSNHOM-UHFFFAOYSA-N

物化性质

• 沸点：
  368.1±35.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  56.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-hydroxyethyl p-tolyl sulfoxide 在 吡啶 、 lithium anion of δ-valerolactam 作用下， 以 四氢呋喃 为溶剂， 生成 1-chlorovinyl p-tolyl sulfoxide
  参考文献：
  名称：

  The first example of γ-chloromagnesio γ-lactones: their generation from γ-tolylsulfinyl γ-lactones with isopropylmagnesium chloride, stability, and reaction with electrophiles

  摘要：

  The treatment of gamma-lactones having a sulfinyl group at the gamma-position, which were synthesized from I-chlorovinyl p-tolyl sulfoxides with lithium enolate of carboxylic esters, with isopropyl magnesium chloride in THF at -78 degrees C gave gamma-chloromagnesio gamma-lactones by the sulfoxide-magnesium exchange reaction in high yields. The generated gamma-chloromagnesio gamma-lactones were found to be stable at below -50 degrees C for at least 2 h. The reaction of these gamma-chloromagnesio gamma-lactones with electrophiles and the stereochemistry of the reactions were investigated. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.09.165
• 作为产物：
  描述：

  2-(对甲苯硫代)-乙醇 在 双氧水 、 溶剂黄146 作用下， 生成 2-hydroxyethyl p-tolyl sulfoxide
  参考文献：
  名称：

  Fromm; Kohn, Chemische Berichte, 1921, vol. 54, p. 323

  摘要：

  DOI：

文献信息

• A novel method for the reduction of sulfoxides with the N,N,N’,N’-tetrabromobenzene-1,3-disulfonamide (TBBDA)/PPh3 system
  作者：Ramin Ghorbani-Vaghei、Lotfi Shiri、Arash Ghorbani-Choghamarani

  DOI：10.1016/j.crci.2013.11.006

  日期：2014.10

  Résumé A new method is described for the reduction of sulfoxides to sulfides using N,N,N’,N’-tetrabromobenzene-1,3-disulfonamide [TBBDA] in combination with triphenylphosphine. Good to excellent yields, short reaction times, high efficiency and facile isolation of the desired products are the advantages of this method.

  摘要 描述了一种使用N,N,N',N'-四溴苯-1,3-二磺酰胺[TBBDA]与三苯基膦结合的方法，将磺氧化物还原为硫化物。该方法具有良好至优异的产率、短反应时间、高效性和便捷的产物分离等优点。
• Fromm; Kohn, Chemische Berichte, 1921, vol. 54, p. 323
  作者：Fromm、Kohn

  DOI：——

  日期：——
• McCormick, Joan E.; McElhinney, R. Stanley, Journal of Chemical Research, Miniprint, 1983, # 7, p. 1736 - 1800
  作者：McCormick, Joan E.、McElhinney, R. Stanley

  DOI：——

  日期：——
• Remote participation during photooxidation at sulfur. Evidence for sulfurane intermediates
  作者：E. L. Clennan、Kang Yang

  DOI：10.1021/jo00042a031

  日期：1992.7

  The photooxidations of geminally substituted gamma-hydroxy sulfides results in formation of unusual oxidative elimination products. Detailed spectral data and the independent synthesis of a close analogue provide compelling evidence for the structures of these olefins. The formation of the olefins is attributed to decomposition of sulfurane intermediates. This conclusion is supported by a detailed kinetic study which separated the chemical, k(r), and physical, k(q), components to the overall deactivation of singlet oxygen. Those sulfides with the best geometry for sulfide-hydroxyl interaction are also the substrates which react most rapidly with singlet oxygen to give oxidation products. In addition, sulfone yields are in excess of 50% for the hydroxy-substituted sulfides but less than 5% for their hydrocarbon analogues. Several mechanisms that provide explanations for these unusually high sulfone yields are presented.
• The first example of γ-chloromagnesio γ-lactones: their generation from γ-tolylsulfinyl γ-lactones with isopropylmagnesium chloride, stability, and reaction with electrophiles
  作者：Shimpei Sugiyama、Hitomi Shimizu、Tsuyoshi Satoh

  DOI：10.1016/j.tetlet.2006.09.165

  日期：2006.12

  The treatment of gamma-lactones having a sulfinyl group at the gamma-position, which were synthesized from I-chlorovinyl p-tolyl sulfoxides with lithium enolate of carboxylic esters, with isopropyl magnesium chloride in THF at -78 degrees C gave gamma-chloromagnesio gamma-lactones by the sulfoxide-magnesium exchange reaction in high yields. The generated gamma-chloromagnesio gamma-lactones were found to be stable at below -50 degrees C for at least 2 h. The reaction of these gamma-chloromagnesio gamma-lactones with electrophiles and the stereochemistry of the reactions were investigated. (c) 2006 Elsevier Ltd. All rights reserved.