[1,1':3',1"-terphenyl]-2'-yl(methyl)sulfane | 1227939-96-9

• 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: [1,1':3',1"-terphenyl]-2'-yl(methyl)sulfane
• 英文别名: 2-Methylsulfanyl-1,3-diphenylbenzene
• CAS: 1227939-96-9
• 化学式: C₁₉H₁₆S
• 分子量: 276.402
• InChiKey: ILUCCUMNSDWUKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  二甲基二硫 、 2,6-二苯基苯胺 在 亚硝酸异戊酯 作用下， 以42%的产率得到[1,1':3',1"-terphenyl]-2'-yl(methyl)sulfane
  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

• Suzuki–Miyaura synthesis of m-terphenyl thioethers and their facilitated oxidation caused by through-space π⋯S⋯π interaction
  作者：Takuhei Yamamoto、Malika Ammam、Sue A. Roberts、George S. Wilson、Richard S. Glass

  DOI：10.1016/j.tet.2016.03.040

  日期：2016.5

  synthesized by Suzuki–Miyaura coupling reactions with 2,6-dibromo-S-tert-butylthio benzene. Selective monocoupling could be achieved with o-substituted boronic acids. This facilitated the synthesis of unsymmetrical S-tert-butyl m-terphenyl thioethers and bis(S-tert-butyl m-terphenyl thioether)s. The study of their electrochemistry showed facilitated oxidations resulting from through-space π⋯S⋯π interactions

  小号-叔丁基米三联苯硫醚已经通过铃木-宫浦偶联反应被有效地合成用2,6-二溴小号-叔丁硫基苯。选择性单偶联可以用邻位取代的硼酸实现。这便于不对称合成小号-叔丁基米三联苯硫醚和双（小号-叔丁基米三联苯硫醚）类。他们的电化学研究表明，通过空间π⋯S⋯π相互作用会促进氧化。
• [EN] MATERIALS FOR ORGANIC ELECTROLUMINESCENT DEVICES<br/>[FR] MATIÈRES POUR DISPOSITIFS ÉLECTROLUMINESCENTS ORGANIQUES
  申请人：MERCK PATENT GMBH

  公开号：WO2017102063A1

  公开（公告）日：2017-06-22

  The present invention relates to compounds of the formula (1) which are suitable for use in electronic devices, in particular organic electroluminescent devices, and to electronic devices which comprise these compounds.

  本发明涉及式（1）的化合物，其适用于电子设备，特别是有机电致发光设备，并且涉及包含这些化合物的电子设备。
• US5932586A
  申请人：——

  公开号：US5932586A

  公开（公告）日：1999-08-03
• 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.