p-tolyl phenacyl sulphoxide | 17530-89-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-tolyl phenacyl sulphoxide
• 英文别名: 1-phenyl-2-(p-tolylsulfinyl)ethan-1-one；p-Tolyl-phenacyl-sulfoxid；Ethanone, 2-[(4-methylphenyl)sulfinyl]-1-phenyl-；2-(4-methylphenyl)sulfinyl-1-phenylethanone
• CAS: 17530-89-1
• 化学式: C₁₅H₁₄O₂S
• 分子量: 258.341
• InChiKey: JQIQTCZCJCVZOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 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-tolyl phenacyl sulphoxide 在 ammonium hydroxide 、 乙酸酐 作用下， 生成 (±)-扁桃酰胺
  参考文献：
  名称：

  Organic synthesis by the Pummerer reaction. II. Synthesis of .alpha.-hydroxy acid derivatives from .beta.-keto sulfoxides

  摘要：

  DOI：

  10.1021/ja00836a021
• 作为产物：
  描述：

  (NE)-N-[2-(4-methylphenyl)sulfinyl-1-phenylethylidene]hydroxylamine 在 benzyltriphenylphosphonium peroxodisulfate 作用下， 以 乙腈 为溶剂， 反应 0.97h， 以98%的产率得到p-tolyl phenacyl sulphoxide
  参考文献：
  名称：

  BENZYLTRIPHENYLPHOSPHONIUM PEROXODISULFATE (PhCH₂PPh₃)₂S₂O8: A MILD AND INEXPENSIVE REAGENT FOR HIGHLY ENANTIOMERIC PURITY OF α-SULFINYL OXIMES AND α-SULFINYL HYDRAZONES TO THE CORRESPONDING β-KETO SULFOXIDES

  摘要：

  Benzyltriphenylphosphonium peroxodisulfate (PhCH2PPh3)zS(2)O(8) (1) is readily prepared as an white solid from benzyltriphenylphosphonium chloride, performs conversion of alpha-sulfinyl oximes (2) and alpha-sulfinyl hydrazones (4) to the corresponding beta-keto sulfoxides (3) in high yields and high enantiomeric purity.

  DOI：

  10.1080/10426500008042103

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。
• 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。
• Solvent-Enabled Radical Selectivities: Controlled Syntheses of Sulfoxides and Sulfides
  作者：Huamin Wang、Qingquan Lu、Chaohang Qian、Chao Liu、Wei Liu、Kai Chen、Aiwen Lei

  DOI：10.1002/anie.201508729

  日期：2016.1.18

  Controlling selectivity is of central importance to radical chemistry. However, the highly reactive and unstable radical intermediates make this task especially challenging. Herein, a strategy for taming radical redox reactions has been developed, in which solvent‐bonding can alter the reactivity of the generated radical intermediates and thereby drastically alter the reaction selectivity at room temperature

  控制选择性对自由基化学至关重要。但是，高反应性和不稳定的自由基中间体使这一任务特别具有挑战性。在此，已经开发出一种用于抑制自由基氧化还原反应的策略，其中溶剂键合可以改变生成的自由基中间体的反应性，从而在室温下极大地改变反应选择性。可以轻松获得各种β-氧亚砜和β-羟基硫化物，其中有些很难用现有方法合成。值得注意的是，在这些方法中金属催化剂或任何其他添加剂都是不必要的。
• Photoredox-Mediated Synthesis of Functionalized Sulfoxides from Terminal Alkynes
  作者：Jaswant Kumar、Ajaz Ahmad、Masood Ahmad Rizvi、Majid Ahmed Ganie、Chhavi Khajuria、Bhahwal Ali Shah

  DOI：10.1021/acs.orglett.0c02055

  日期：2020.7.17

  A photoredox-mediated protocol for the synthesis of α-alkoxy-β-ketosulfoxides and α,β-dialkoxysulfoxides using alkynes, thiol, and alcohols is reported. This work presents a rare single-step synthesis of α-substituted sulfoxides, involving tandem introduction of a thiol and alcohol as a key enabling advancement. Furthermore, the method can be easily employed to access vinyl sulfoxides and β-ketosulfoxides

  报道了使用炔烃，硫醇和醇类的光氧化还原介导的方案，用于合成α-烷氧基-β-酮亚砜和α，β-二烷氧基亚砜。这项工作提出了一种罕见的单步合成α-取代的亚砜的方法，涉及串联引入硫醇和醇作为实现改进的关键。此外，该方法可以容易地用于获得乙烯基亚砜和β-酮亚砜。
• 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。