1-(ethoxycarbonyl)ethyl phenyl sulfoxide | 90425-30-2

• 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: 1-(ethoxycarbonyl)ethyl phenyl sulfoxide
• 英文别名: ethyl α-sulfinylphenylpropionate；ethyl 2-(phenylsulfinyl)propanoate；ethyl (phenylsulfinyl)propanoate；Ethyl 2-(benzenesulfinyl)propanoate
• CAS: 90425-30-2；90425-31-3；56631-66-4
• 化学式: C₁₁H₁₄O₃S
• 分子量: 226.296
• InChiKey: DVXUVHRWZPTJMO-UHFFFAOYSA-N

物化性质

• 沸点：
  363.8±25.0 °C(Predicted)
• 密度：
  1.21±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(ethoxycarbonyl)ethyl phenyl sulfoxide 以 1,4-二氧六环 为溶剂， 生成 丙烯酸乙酯
  参考文献：
  名称：

  Tsukurimichi, Eiichi; Yoshimura, Toshiaki; Yoshizawa, Masaki, Phosphorus, Sulfur and Silicon and the Related Elements, 1989, vol. 46, p. 113 - 120

  摘要：

  DOI：
• 作为产物：
  描述：

  2-氯丙酸乙酯 在 溴 、 silica gel 、 三乙胺 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 1-(ethoxycarbonyl)ethyl phenyl sulfoxide
  参考文献：
  名称：

  A Facile and Selective Procedure for Oxidation of Sulfides to Sulfoxides with Molecular Bromine on Hydrated Silica Gel in Dichloromethane

  摘要：

  DOI：

  10.1055/s-1998-6097

文献信息

• .ALPHA.-Fluorination of Methyl Phenyl Sulfoxide and Related Compounds by Molecular Fluorine: A Novel Method for the Introduction of Fluorine into Sulfoxides Bearing .ALPHA.-H Atoms.
  作者：Akemi TOYOTA、Yoshinori ONO、Jun CHIBA、Takumichi SUGIHARA、Chikara KANEKO

  DOI：10.1248/cpb.44.703

  日期：——

  Direct formation of α-fluorosulfones from sulfoxides bearing α-H atoms merely by reaction with molecular fluorine (5% F2/N2) is reported, and a novel non-Pummerer-type mechanism is proposed for this α-fluorination reaction.

  据报道，通过与分子氟（5% F2/N2）反应，仅直接从含有α-H原子的亚砜生成α-氟磺醚，为此α-氟化反应提出了一种新型非Pummerer型机理。
• A Facile and Selective Procedure for Oxidation of Sulfides to Sulfoxides on Silica Gel Supported Magnesium Monoperoxyphthalate (MMPP) in Dichloromethane
  作者：Mohammed Hashmat Ali、William C. Stevens

  DOI：10.1055/s-1997-1420

  日期：1997.7

  The scope of the magnesium monoperoxyphthalate (MMPP) oxidation of sulfides to sulfoxides has been extended by using hydrated silica gel as a solid support in dichloromethane media. This procedure works in the presence of a number of functional groups on the sulfides, including carbonyl and alkene groups that have been known to undergo Baeyer-Villiger oxidation and epoxidation with MMPP when using more conventional procedures. To our knowledge, this is the first example of oxidation of sulfides containing a carbonyl group with MMPP in non-aqueous media without any Baeyer-Villiger reaction. The reported procedure is easy to perform, product separation is trivial and it produces excellent yields.

  水合硅胶作为固体载体在二氯甲烷介质中扩大了镁单过氧邻苯二甲酸酯(MMPP)对硫化物氧化生成亚砜的适用范围。该方法在硫化物中含有多种官能团的情况下均有效，包括已知在常规方法中会与MMPP发生拜耶尔-维利格氧化和环氧化反应的羰基和烯烃官能团。据我们所知，这是首次在非水介质中使用MMPP对含有羰基的硫化物进行氧化而不发生拜耶尔-维利格反应的例子。该方法操作简便，产物分离简单，且产率优异。
• Oxidation of Sulfides with N‐Bromosuccinimide in the Presence of Hydrated Silica Gel
  作者：Mohammed Hashmat Ali、Melanie Hartman、Kimberly Lamp、Chad Schmitz、Tim Wencewicz

  DOI：10.1080/00397910600618988

  日期：2006.7

  Abstract An efficient and highly selective procedure for oxidation of sulfides to sulfoxides with N‐bromosuccinimide (NBS) in the presence of hydrated silica gel has been developed. Hydrated silica gel supplies the water necessary for decomposition of the intermediate bromosulfonium salt to the product, allowing the reaction to employ a nonaqueous media. Also, this procedure has increased the scope

  摘要 开发了一种在水合硅胶存在下用 N-溴代琥珀酰亚胺 (NBS) 将硫化物氧化成亚砜的高效且高选择性的方法。水合硅胶为产物提供中间体溴锍盐分解所需的水，使反应能够使用非水介质。此外，该过程通过氧化更广泛的硫化物扩大了反应范围，这在以前是不可能的。
• Pummerer Reaction of Sulfoxides in Acetic Anhydride Catalyzed by Al-MCM-41
  作者：Suguru Ito、Yoshihiro Kubota、Masatoshi Asami

  DOI：10.1246/cl.150896

  日期：2016.1.5

  The Pummerer reaction of acetic anhydride with both alkyl aryl sulfoxides and dialkyl sulfoxides was efficiently promoted by a mesoporous aluminosilicate Al-MCM-41 to afford the corresponding α-ace...

  乙酸酐与烷基芳基亚砜和二烷基亚砜的Pummerer反应被介孔铝硅酸盐Al-MCM-41有效促进，得到相应的α-ace...
• Selective and mild oxidation of sulfides to sulfoxides by oxodiperoxo molybdenum complexes adsorbed onto silica gel
  作者：Fabiana Batigalhia、Marcelo Zaldini-Hernandes、Antônio G Ferreira、Ivani Malvestiti、Quezia B Cass

  DOI：10.1016/s0040-4020(01)00969-3

  日期：2001.11

  Aliphatic and aromatic sulfides, ketosulfides, sulfinyl acids and esters, and olefinic sulfides were oxidized to sulfoxides using oxodiperoxo complexes of molybdenum coated on silica gel (150 Å pore size) in very high yields. Complete chemoselectivity was observed for the oxidation of all functional sulfides. Sulfones were, however, the main products of the reaction when the complexes were not coated

  使用涂在硅胶上（孔径为150Å）的钼的氧代二氧杂配合物，脂肪族和芳香族硫化物，酮硫醚，亚磺酸基酸和酯以及烯属硫化物被氧化为亚砜。观察到所有功能性硫化物的氧化具有完全的化学选择性。然而，当配合物未涂覆在硅胶上时，砜是反应的主要产物。还研究了硅胶作为这些反应支持物的影响，并证明了它改变了配合物的反应性，但对配合物的优异的化学选择性不负责任。络合物[MoO（O 2）2（吡唑）（H 2 O）]被证明比[MoO（O 2）具有更高的反应性2（Opyr）（H 2 O）]。