1-(3-methoxyphenyl)-2-(phenylsulfinyl)ethanone | 128867-25-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(3-methoxyphenyl)-2-(phenylsulfinyl)ethanone
• 英文别名: 2-(Benzenesulfinyl)-1-(3-methoxyphenyl)ethanone
• CAS: 128867-25-4
• 化学式: C₁₅H₁₄O₃S
• 分子量: 274.34
• InChiKey: MBVHMPJCTCRVRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  62.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 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 2.0h， 生成 1-(3-methoxyphenyl)-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

• 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。
• A New Synthesis of β-Keto Sulfoxides from Chloromethyl Aryl Sulfoxide and Aldehydes
  作者：Tsuyoshi Satoh、Takako Fujii、Koji Yamakawa

  DOI：10.1246/bcsj.63.1266

  日期：1990.4

  Addition of the carbanion of chloromethyl aryl sulfoxide to aldehyde gave the adduct, which was treated with three-equivalents of lithium diisopropylamide (LDA) to afford β-keto sulfoxide in high overall yield.

  将氯甲基芳基亚砜的碳负离子加成到醛中得到加合物，将其用三当量的二异丙基氨基锂（LDA）处理，以高总产率得到 β-酮亚砜。
• SATOH, TSUYOSHI;FUJII, TAKAKO;YAMAKAWA, KOJI, BULL. CHEM. SOC. JAP., 63,(1990) N, C. 1266-1268
  作者：SATOH, TSUYOSHI、FUJII, TAKAKO、YAMAKAWA, KOJI

  DOI：——

  日期：——
• 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.