1,3-Bis(2-methoxyphenyl)-2-phenylsulfanylbenzene | 1227939-98-1

• 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: 1,3-Bis(2-methoxyphenyl)-2-phenylsulfanylbenzene
• CAS: 1227939-98-1
• 化学式: C₂₆H₂₂O₂S
• 分子量: 398.525
• InChiKey: HQGBSSIQJIRQLA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  43.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  二苯二硫醚 、 1,3-二氯苯 、 alkaline earth salt of/the/ methylsulfuric acid 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以54%的产率得到1,3-Bis(2-methoxyphenyl)-2-phenylsulfanylbenzene
  参考文献：
  名称：

  Synthesis and Structure of m-Terphenyl Thio-, Seleno-, and Telluroethers

  摘要：

  Several routes for the synthesis of m-terphenyl thio-, seleno-, and telluroethers were investigated. m-Terphenyl iodides react with diphenyl diselenides or ditellurides (CsOH center dot H2O, DMSO, 110 degrees C) to give the desired compounds in 19-84% yield which significantly extends the previously reported such reactions because o-benzyne cannot be an intermediate as previously suggested. However, the most general synthetic route was that involving reaction of 2,6-diaryl Grignard reagents with sulfur, selenium, or tellurium electrophiles. The m-terphenyl thio-, seleno-, and telluroethers were characterized spectroscopically and, in one case, by single-crystal X-ray analysis. Certain of these compounds showed atropisomerism and barriers for interconversion of isomers were determined by variable-temperature NMR spectroscopy. The barriers for interconverting the syn and anti atropisomers increase on going from the analogous S to Se to Te compounds. Calculations on this isomerization revealed that the barriers are due to rotation about the aryl-aryl bond and that the barriers for rotation about the aryl-chalcogen bond are much lower.

  DOI：

  10.1021/jo101299x

文献信息

• Synthesis and Structure of <i>m</i>-Terphenyl Thio-, Seleno-, and Telluroethers
  作者：Uzma I. Zakai、Anna Błoch-Mechkour、Neil E. Jacobsen、Leif Abrell、Guangxin Lin、Gary S. Nichol、Thomas Bally、Richard S. Glass

  DOI：10.1021/jo101299x

  日期：2010.12.17

  Several routes for the synthesis of m-terphenyl thio-, seleno-, and telluroethers were investigated. m-Terphenyl iodides react with diphenyl diselenides or ditellurides (CsOH center dot H2O, DMSO, 110 degrees C) to give the desired compounds in 19-84% yield which significantly extends the previously reported such reactions because o-benzyne cannot be an intermediate as previously suggested. However, the most general synthetic route was that involving reaction of 2,6-diaryl Grignard reagents with sulfur, selenium, or tellurium electrophiles. The m-terphenyl thio-, seleno-, and telluroethers were characterized spectroscopically and, in one case, by single-crystal X-ray analysis. Certain of these compounds showed atropisomerism and barriers for interconversion of isomers were determined by variable-temperature NMR spectroscopy. The barriers for interconverting the syn and anti atropisomers increase on going from the analogous S to Se to Te compounds. Calculations on this isomerization revealed that the barriers are due to rotation about the aryl-aryl bond and that the barriers for rotation about the aryl-chalcogen bond are much lower.