p-bromophenyl phenacyl sulfoxide | 22773-47-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-bromophenyl phenacyl sulfoxide
• 英文别名: benzoylmethyl 4-bromophenyl sulfoxide；2-[(4-bromophenyl)sulfinyl]-1-phenylethan-1-one；p-Brom-phenyl-phenacyl-sulfoxid；2-(4-Bromophenyl)sulfinyl-1-phenylethanone
• CAS: 22773-47-3
• 化学式: C₁₄H₁₁BrO₂S
• mdl: MFCD21421818
• 分子量: 323.21
• InChiKey: GVPHJLOHAYNPOA-UHFFFAOYSA-N

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：

  p-bromophenyl phenacyl sulfoxide 、 乙腈 在 三氟甲磺酸酐 作用下， 反应 0.5h， 以86%的产率得到4-((4-bromophenyl)thio)-2-methyl-5-phenyloxazole
  参考文献：
  名称：

  Tf2O 介导的 β-酮亚砜和腈直接合成 4-亚磺酰化恶唑

  摘要：

  描述了一种合成 4-亚磺酰化恶唑的通用且有效的方法。由 β-酮亚砜和腈以良好至优异的产率获得三取代的恶唑。机理研究表明，反应通过将腈亲核加成原位形成的 α-羰基阳离子，然后进行分子内环化来进行。

  DOI：

  10.1021/acs.joc.2c01630
• 作为产物：
  描述：

  2-(4-bromophenylthio)-1-phenylethanone 在 过氧乙酸 作用下， 生成 p-bromophenyl phenacyl sulfoxide
  参考文献：
  名称：

  The synthesis of chiral β-ketosulfoxides by enantioselective oxidation and their stereocontrolled reduction to β-hydroxysulfoxides

  摘要：

  Various chiral non-racemic beta-ketosulfoxides, a class of compounds frequently used in asymmetric synthesis, were prepared in good yields by tert-butyl hydroperoxide oxidation of the corresponding sulfides in the presence of a complex between titanium and (S,S)-hydrobenzoin. The ee values of almost all of the purified products were > 98%. As ascertained by X-ray analysis and/or by NMR spectroscopy, the use of the (S,S)-form of the ligand led to aryl beta-ketosulfoxides with (R-S)-configuration and to methyl phenacyl sulfoxide with the (S-S)-configuration. Some of the aryl ketosulfoxides were subjected to reduction with DIBAL-H/ZnCl2 and the corresponding beta-sulfinylalcohols with an (R,R-S)-configuration produced. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.12.004

文献信息

• Switchable Synthesis of Sulfoxides and α-Alkoxy-β-ketothioethers Regulated by Temperature in a Selectfluor–Methanol System
  作者：Jiateng Wang、Mengxia Liu、Yue Zhang、Gehua Bi、Yi Zhao、Kai Yang、Xin Huang

  DOI：10.1021/acs.joc.1c01146

  日期：2021.11.5

  A switchable and benign protocol for chemoselective synthesis of sulfoxides and α-alkoxy-β-ketothioethers has been developed. It was determined that various thiophenols and alkenes/alkynes are compatible to realize the target compounds from a medium to a high yield by regulating the reaction temperature. In particular, methanol not only served as a solvent but also participated in the reaction process

  亚砜和 α-烷氧基-β-酮硫醚的化学选择性合成的可切换和良性协议已经开发。确定了各种苯硫酚和烯烃/炔烃相容，通过调节反应温度实现目标化合物从中等收率到高收率。特别是甲醇不仅作为溶剂，而且作为氢供体参与反应过程。在这项研究中，Selectfluor 已被证明是反应系统中一种高效的多功能试剂。
• 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...
• 一种含硫2，4，5-三取代噁唑类化合物及其制备方法和应用
  申请人：山东理工大学

  公开号：CN114790179A

  公开（公告）日：2022-07-26

  本发明提供一种含硫2，4，5‑三取代噁唑类化合物，其特征在于，具有如式I所示的结构：其中，R1选自萘环、芳杂基、C1‑4烃基、苯基或者含有环上取代基团的苯环；R2选自：环己基、苄基、苯基或者含有环上取代基团的苯环；R3选自：C1‑4烃基、乙烯基、环戊基、苄基苯基或者含有环上取代基团的苯环。本发明还提供了对应的制备方法和应用。克服了传统合成方法中前体合成复杂，反应体系复杂，副产物多等缺点。
• The synthesis of chiral β-ketosulfoxides by enantioselective oxidation and their stereocontrolled reduction to β-hydroxysulfoxides
  作者：Cosimo Cardellicchio、Omar Hassan Omar、Francesco Naso、Maria Annunziata M. Capozzi、Francesco Capitelli、Valerio Bertolasi

  DOI：10.1016/j.tetasy.2005.12.004

  日期：2006.1

  Various chiral non-racemic beta-ketosulfoxides, a class of compounds frequently used in asymmetric synthesis, were prepared in good yields by tert-butyl hydroperoxide oxidation of the corresponding sulfides in the presence of a complex between titanium and (S,S)-hydrobenzoin. The ee values of almost all of the purified products were > 98%. As ascertained by X-ray analysis and/or by NMR spectroscopy, the use of the (S,S)-form of the ligand led to aryl beta-ketosulfoxides with (R-S)-configuration and to methyl phenacyl sulfoxide with the (S-S)-configuration. Some of the aryl ketosulfoxides were subjected to reduction with DIBAL-H/ZnCl2 and the corresponding beta-sulfinylalcohols with an (R,R-S)-configuration produced. (c) 2005 Elsevier Ltd. All rights reserved.
• Tf₂O-Mediated Direct Synthesis of 4-Sulfenylated Oxazoles from β-Keto Sulfoxides and Nitriles
  作者：Jiateng Wang、Yunqing Zhuang、Bingxue Yu、Xiaofeng Wang、Gehua Bi、Xin Huang、Weimin Zhang

  DOI：10.1021/acs.joc.2c01630

  日期：2022.11.4

  A general and efficient method for the synthesis of 4-sulfenylated oxazoles is described. Trisubstituted oxazoles are obtained in good to excellent yields from β-keto sulfoxides and nitriles. The mechanistic study suggests that the reaction proceeds via the nucleophilic addition of nitriles to the in situ formed α-carbonyl cation followed by intramolecular cyclization.

  描述了一种合成 4-亚磺酰化恶唑的通用且有效的方法。由 β-酮亚砜和腈以良好至优异的产率获得三取代的恶唑。机理研究表明，反应通过将腈亲核加成原位形成的 α-羰基阳离子，然后进行分子内环化来进行。