1-[2-(4-Methoxyphenyl)sulfanylphenyl]hexan-2-one | 1190852-59-5

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-[2-(4-Methoxyphenyl)sulfanylphenyl]hexan-2-one
• 英文别名: 1-[2-(4-methoxyphenyl)sulfanylphenyl]hexan-2-one
• CAS: 1190852-59-5
• 化学式: C₁₉H₂₂O₂S
• 分子量: 314.448
• InChiKey: VPVKVRPNQGYUON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  51.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  苯基对甲氧基苯基亚砜 、 1-己炔 在 silver hexafluoroantimonate 、 三苯基膦氯金 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 1-(5-Methoxy-2-phenylsulfanylphenyl)hexan-2-one 、 1-[2-(4-Methoxyphenyl)sulfanylphenyl]hexan-2-one
  参考文献：
  名称：

  Gold(I)-Catalyzed Intermolecular Oxyarylation of Alkynes: Unexpected Regiochemistry in the Alkylation of Arenes

  摘要：

  The reaction between acetylenes and sulfoxides, studied as a test case for gold-catalyzed intermolecular addition, provides the oxyarylation compounds 3 in good yields. Unpredictably, in all cases a single regioisomer arising from the electrophilic aromatic alkylation at the position adjacent to the sulfur atom is obtained instead of the expected Friedel-Crafts regioisomer. A new concerted mechanism based on DFT calculations is proposed to account for the products in this intermolecular gold(I)-catalyzed reaction.

  DOI：

  10.1021/ol9020578

文献信息

• Gold(I)-Catalyzed Intermolecular Oxyarylation of Alkynes: Unexpected Regiochemistry in the Alkylation of Arenes
  作者：Ana B. Cuenca、Sergi Montserrat、Kabir M. Hossain、Gisela Mancha、Agustí Lledós、Mercedes Medio-Simón、Gregori Ujaque、Gregorio Asensio

  DOI：10.1021/ol9020578

  日期：2009.11.5

  The reaction between acetylenes and sulfoxides, studied as a test case for gold-catalyzed intermolecular addition, provides the oxyarylation compounds 3 in good yields. Unpredictably, in all cases a single regioisomer arising from the electrophilic aromatic alkylation at the position adjacent to the sulfur atom is obtained instead of the expected Friedel-Crafts regioisomer. A new concerted mechanism based on DFT calculations is proposed to account for the products in this intermolecular gold(I)-catalyzed reaction.