2-(methylsulfinyl)phenyl phenyl ether | 395090-42-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(methylsulfinyl)phenyl phenyl ether
• 英文别名: methyl 2-phenoxyphenyl sulfoxide；1-Methylsulfinyl-2-phenoxybenzene
• CAS: 395090-42-3
• 化学式: C₁₃H₁₂O₂S
• 分子量: 232.303
• InChiKey: XTVAVBRTNOUXEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  三氟甲磺酸 、 2-(methylsulfinyl)phenyl phenyl ether 以 四氯化碳 为溶剂， 反应 24.0h， 以97%的产率得到5-methylphenoxathiinium triflate
  参考文献：
  名称：

  Synthetic Routes to Polyheteroacenes:  Characterization of a Heterocyclic Ladder Polymer Containing Phenoxathiinium-type Building Blocks

  摘要：

  The synthetic routes to ladder polymers that consist of benzenetetrayl subunits with oxo and methylsulfonio linkages are described. As the key intermediate, poly(phenylene oxide)s having pendant methylsulfenyl groups are prepared by copper-catalyzed oxidative polymerization of the corresponding phenols with O-2. The oxidation of the polymer with an equimolar amount of H2O2 in the presence of acetic acid effects the high-yielding conversion of methylsulfenyl to methylsulfinyl groups without the formation of the undesired methylsulfonyl groups. The superacidified condensation of the resulting polymer (Swern reaction of aryl sulfoxides) under dilution conditions induces the polymer-analogous intramolecular electrophilic ring-closing reaction of the hydroxymethylphenylsulfonium cation onto the adjacent benzene ring to yield the required ladder polymer, which has proved to be a semiconductor with an intrinsic electric conductivity of 2 x 10(-5) S/cm. A comparison of the spectroscopic properties of the ladder polymer with those of the model compounds such as 5-methylphenoxathiinium triflate and phenoxathiin discloses pi -electron delocalization over the methylsulfonio linkages, demonstrating the efficacy of the ladderization for p-pi /d-pi interactions in arylsulfonium moieties. This synthetic approach permits the thio and alkylsulfonio ladder linkages for a variety of phenyl ethers to form in high yields.

  DOI：

  10.1021/ma010961d
• 作为产物：
  描述：

  2-溴茴香硫醚 在 双氧水 、 sodium methylate 、 copper(l) chloride 作用下， 以 二氯甲烷 、 水 、 溶剂黄146 、 苯酚 为溶剂， 反应 48.0h， 生成 2-(methylsulfinyl)phenyl phenyl ether
  参考文献：
  名称：

  Synthetic Routes to Polyheteroacenes:  Characterization of a Heterocyclic Ladder Polymer Containing Phenoxathiinium-type Building Blocks

  摘要：

  The synthetic routes to ladder polymers that consist of benzenetetrayl subunits with oxo and methylsulfonio linkages are described. As the key intermediate, poly(phenylene oxide)s having pendant methylsulfenyl groups are prepared by copper-catalyzed oxidative polymerization of the corresponding phenols with O-2. The oxidation of the polymer with an equimolar amount of H2O2 in the presence of acetic acid effects the high-yielding conversion of methylsulfenyl to methylsulfinyl groups without the formation of the undesired methylsulfonyl groups. The superacidified condensation of the resulting polymer (Swern reaction of aryl sulfoxides) under dilution conditions induces the polymer-analogous intramolecular electrophilic ring-closing reaction of the hydroxymethylphenylsulfonium cation onto the adjacent benzene ring to yield the required ladder polymer, which has proved to be a semiconductor with an intrinsic electric conductivity of 2 x 10(-5) S/cm. A comparison of the spectroscopic properties of the ladder polymer with those of the model compounds such as 5-methylphenoxathiinium triflate and phenoxathiin discloses pi -electron delocalization over the methylsulfonio linkages, demonstrating the efficacy of the ladderization for p-pi /d-pi interactions in arylsulfonium moieties. This synthetic approach permits the thio and alkylsulfonio ladder linkages for a variety of phenyl ethers to form in high yields.

  DOI：

  10.1021/ma010961d

文献信息

• Supramolecular Activation of Hydrogen Peroxide in the Selective Sulfoxidation of Thioethers by a Self-Assembled Hexameric Capsule
  作者：Giorgio La Sorella、Laura Sperni、Giorgio Strukul、Alessandro Scarso

  DOI：10.1002/adsc.201600430

  日期：2016.11.3

  An efficient metal‐free organocatalytic activation of hydrogen peroxide (H2O2) towards thioethers leading to the corresponding sulfoxides in high yields at room temperature within hours was promoted by the hexameric capsule formed by the self‐assembly of resorcin[4]arene units. The capsule plays a dual role of activating the oxidant through hydrogen bonding and favouring the oxidation reaction inside

  间苯二酚[4]芳烃单元的自组装形成的六聚体胶囊促进了过氧化氢（H 2 O 2）向硫醚的高效无金属有机催化活化，从而在室温下数小时内以高收率产生了相应的亚砜。 。胶囊起着双重作用，即通过氢键活化氧化剂并促进腔体内的氧化反应。通过使用竞争性铵客体，模仿了竞争性抑制剂对酶的失活，观察到超分子有机催化剂的失活。