2,6-diiodo-4-(methylthio)anisole | 128733-84-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2,6-diiodo-4-(methylthio)anisole
• 英文别名: 2,6-diiodo-4-methylthioanisole；1,3-diiodo-5-methyl-2-methylsulfanylbenzene
• CAS: 128733-84-6
• 化学式: C₈H₈I₂S
• 分子量: 390.027
• InChiKey: FWGZLCYGACDVHM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.93
• 重原子数：
  11.0
• 可旋转键数：
  1.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  2,6-diiodo-4-(methylthio)anisole 在 氢氧化钾 、 四(三苯基膦)钯 、 乙醇 、 三溴化硼 、 sodium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 异丙醇 、 苯 为溶剂， 反应 239.0h， 生成 4-tert-butyl-2-[3-[5-tert-butyl-2-hydroxy-3-(hydroxymethyl)phenyl]-5-methyl-2-methylsulfanylphenyl]-6-(hydroxymethyl)phenol
  参考文献：
  名称：

  Host-guest complexation. 53. Functional groups preorganized in hemispherands for binding alkali metal and ammonium cations

  摘要：

  DOI：

  10.1021/jo00302a028
• 作为产物：
  描述：

  2,6-二碘-4-甲基苯胺 生成 2,6-diiodo-4-(methylthio)anisole
  参考文献：
  名称：

  BRYANT, JUDI A.;HELGESON, ROGER C.;KNOBLER, CAROLYN B.;DEGRANDPRE, MARK P+, J. ORG. CHEM., 55,(1990) N5, C. 4622-4634

  摘要：

  DOI：

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.