1-(4-bromophenyl)-2-(phenylsulfinyl)ethanone | 17698-51-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-bromophenyl)-2-(phenylsulfinyl)ethanone
• 英文别名: 4-bromophenylcarbonylmethyl phenyl sulfoxide；Phenyl-(4-brom-phenacyl)-sulfoxid；2-(Benzenesulfinyl)-1-(4-bromophenyl)ethanone
• CAS: 17698-51-0
• 化学式: C₁₄H₁₁BrO₂S
• mdl: MFCD21421690
• 分子量: 323.21
• InChiKey: HZMKPAOMHWEECN-UHFFFAOYSA-N

物化性质

• 熔点：
  90-94 °C
• 沸点：
  507.0±35.0 °C(Predicted)
• 密度：
  1.58±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.071
• 拓扑面积：
  53.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-bromophenyl)-2-(phenylsulfinyl)ethanone 、 乙酸酐 在 aluminum-incorporated MCM-41 作用下， 反应 1.0h， 以88%的产率得到4-bromophenylcarbonyl(phenylthio)methyl acetate
  参考文献：
  名称：

  Al-MCM-41催化乙酐中亚砜的Pummerer反应

  摘要：

  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...

  DOI：

  10.1246/cl.150896
• 作为产物：
  描述：

  甲基苯基亚砜 在 吡啶 、 四(三苯基膦)钯 、 溴 、 cesium fluoride 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 3.0h， 生成 1-(4-bromophenyl)-2-(phenylsulfinyl)ethanone
  参考文献：
  名称：

  First Synthesis of β-Keto Sulfoxides by a Palladium-Catalyzed Carbonylative Suzuki Reaction

  摘要：

  An unprecedented palladium-catalyzed three-component cross-coupling reaction between alpha-bromo sulfoxide, carbon monoxide, and aromatic boronic acids provides a new and efficient approach to the synthesis of beta-ketosulfoxides. The reaction takes place under mild conditions with a wide range of variously substituted aryl and heteroaryl boronic acids. The carbonylative cross-coupling reaction is strongly favored over competing direct cross-coupling and homocoupling processes, except with boronic acids carrying strong electron-withdrawing substituents.

  DOI：

  10.1021/ol0518737

文献信息

• Nuclear Magnetic Resonance Studies of Sulfur Compounds. II. The Substituent Effect on Geminal Coupling Constants and on Magnetic Nonequivalence of the Methylene Protons of Sulfoxides.
  作者：Motohiro Nishio

  DOI：10.1248/cpb.15.1669

  日期：——

  Nuclear magnetic resonance spectra were obtained for a number of sulfoxides, whose methylene protons are magnetically nonequivalent. The coupling constants between these protons depend on the electronic properties of the substituent adjacent to the coupling protons. The substituent effect on magnetic nonequivalence was also studied and it is demonstrated that the electronic properties of the substituent constitute an important factor responsible for the magnitude of magnetic nonequivalence.

  为若干亚砜得到了核磁共振谱，它们的甲撑质子在磁性上是属于非等性的。这些质子之间的偶合常数依赖于和偶合质子临近的取代基的电子性质。也对取代基对磁性非等性的影响作了研究，并证明取代基的电子性质是对磁性非等性大小起决定作用的一个重要因素。
• Visible light organophotoredox catalysis: a general approach to β-keto sulfoxidation of alkenes
  作者：Twinkle Keshari、Vinod K. Yadav、Vishnu P. Srivastava、Lal Dhar S. Yadav

  DOI：10.1039/c4gc00857j

  日期：——

  A mild, simple, efficient and metal-free approach to β-keto sulfoxides utilising eosin Y as an organophotoredox catalyst has been developed. This general protocol offers a direct and rapid difunctionalization of alkenes using thiophenols and atmospheric oxygen at room temperature in a one-pot procedure. The utilisation of visible light and air (O2) as inexpensive, readily available, non-toxic and eco-sustainable

  已经开发出一种温和，简单，有效且不含金属的方法，利用曙红Y作为有机光氧化还原催化剂来合成β-酮亚砜。该通用方案在室温下通过一锅法使用硫酚和大气中的氧气提供了烯烃的直接快速双官能化。可见光和空气（O 2）作为廉价，易于获得，无毒且生态可持续的试剂的利用使该协议与绿色化学要求兼容。
• 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...
• First Synthesis of β-Keto Sulfoxides by a Palladium-Catalyzed Carbonylative Suzuki Reaction
  作者：Mercedes Medio-Simón、Cristian Mollar、Nuria Rodríguez、Gregorio Asensio

  DOI：10.1021/ol0518737

  日期：2005.10.1

  An unprecedented palladium-catalyzed three-component cross-coupling reaction between alpha-bromo sulfoxide, carbon monoxide, and aromatic boronic acids provides a new and efficient approach to the synthesis of beta-ketosulfoxides. The reaction takes place under mild conditions with a wide range of variously substituted aryl and heteroaryl boronic acids. The carbonylative cross-coupling reaction is strongly favored over competing direct cross-coupling and homocoupling processes, except with boronic acids carrying strong electron-withdrawing substituents.