1,3,5-tris(phenylthio)benzene | 3379-62-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1,3,5-tris(phenylthio)benzene
• 英文别名: 1,3,5-Tris-(phenylthio)-benzol；1,3,5-tri(phenylthio)benzene；1,3,5-Tris(phenylsulfanyl)benzene
• CAS: 3379-62-2
• 化学式: C₂₄H₁₈S₃
• 分子量: 402.605
• InChiKey: SZKJBOSLHMISRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  75.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,3,5-三溴苯 、 In(SPh)₃ 在 palladium diacetate 、 N,N-二异丙基乙胺 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以96%的产率得到1,3,5-tris(phenylthio)benzene
  参考文献：
  名称：

  Synthesis of Di-, Tri-, and Tetrasulfides through Multifold Carbon−Sulfur Cross-Coupling Reactions with Indium Tri(organothiolates) in a One-Pot Procedure

  摘要：

  Pd-catalyzed multifold (2-, 3-, and 4-fold) carbon sulfur cross-coupling reaction of indium tri(organothiolates) with polybromonated aromatic and heteroaromatic compounds was developed in a one-pot procedure. Both 2,5-dibromopyridine and 2,6-dibromopyridine reacted with indium tri(organothiolates) (0.68 equiv) in the presence of 4 mol A of Pd(OAc)(2), 4.2 mol % of Xantphos, and 1 equiv of diisopropylethylamine (DIPEA), producing disulfides in good to excellent yields. These results indicate that indium tri(organothiolates) transfer all three alkyl- or arylthio groups attached to indium metal to electrophilic coupling partners. Indium tri(organothiolates) derived from alkyl thiol having a low boiling point, such as n-propyl, isopropyl, and tert-butyl thiol, acted as good nucleophilic coupling partners. In addition, indium tri(arylthiolates) derived from aryl thiols possessing an electron-withdrawing or -donating group on the aromatic ring participated well in the Pd-catalyzed multifold carbon sulfur cross-coupling reaction. 4,4'-Dibromo-1,1'-biphenyl, 9,10-dibromoanthracene, 2,4-dibromoanisole, 2,7-dibromo-9,9-dimethylfluorene, 3,4-dibromothiophene, 2,3-dibromothiophene, 2,2'-bithiophene, 1,3,5-tribromobenzene, and 1,2,4,5-tetrabromobenzene were converted smoothly to the corresponding di-, tri-, and tetrasulfides.

  DOI：

  10.1021/jo102441t

文献信息

• A semiconducting supramolecular Co(<scp>ii</scp>)-metallohydrogel: an efficient catalyst for single-pot aryl–S bond formation at room temperature
  作者：Subhendu Dhibar、Amiya Dey、Rajkumar Jana、Arpita Chatterjee、Gourab Kanti Das、Partha Pratim Ray、Biswajit Dey

  DOI：10.1039/c9dt03373d

  日期：——

  A monoethanolamine based Co(ii)-metallohydrogel can act as a Schottky barrier diode device and a catalyst for single-pot aryl–S bond formation at room temperature.

  一种基于单乙醇胺的Co（II）-金属水凝胶可以作为肖特基势垒二极管器件，并且可以在室温下作为单锅芳基-S键形成的催化剂。
• Optical materials and optical part each containing aromatic sulfide compound and aromatic sulfide compound
  申请人：——

  公开号：US20030085387A1

  公开（公告）日：2003-05-08

  Optical materials with improved heat resistance, especially dopant-type GI POFs with improved heat resistance are provided. These optical materials each comprises at least one aromatic sulfide compound represented by the following formula (1): 1 wherein n stands for an integer of from 2 to 12, k stands for an integer of from 1 to n, A represents a substituted or unsubstituted, n-valent carbocyclic aromatic ring or heterocyclic aromatic ring, and B 1 to B n each independently represent a substituted or unsubstituted, carbocyclic aromatic group or heterocyclic aromatic group.

  提供了具有改进热稳定性的光学材料，特别是具有改进热稳定性的掺杂型GI POFs。这些光学材料每个包括至少一种由以下公式（1）表示的芳香硫化合物：1其中n代表2至12的整数，k代表1至n的整数，A代表取代或未取代的n价碳环芳香环或杂环芳香环，而B1至Bn各自独立地代表取代或未取代的碳环芳香基或杂环芳香基。
• OPTICAL MATERIAL AND OPTICAL PART EACH CONTAINING AROMATIC SULFIDE COMPOUND AND AROMATIC SULFIDE COMPOUND
  申请人：Mitsui Chemicals, Inc.

  公开号：EP1291679A1

  公开（公告）日：2003-03-12

  Optical materials with improved heat resistance, especially dopant-type GI POFs with improved heat resistance are provided. These optical materials each comprises at least one aromatic sulfide compound represented by the following formula (1): wherein    n stands for an integer of from 2 to 12,    k stands for an integer of from 1 to n,    A represents a substituted or unsubstituted, n-valent carbocyclic aromatic ring or heterocyclic aromatic ring, and    B1 to Bn each independently represent a substituted or unsubstituted, carbocyclic aromatic group or heterocyclic aromatic group.

  本研究提供了耐热性更好的光学材料，特别是耐热性更好的掺杂型 GI POF。这些光学材料各自包含至少一种由下式（1）表示的芳香族硫化物化合物： 其中 n 代表 2 到 12 之间的整数、 k 代表 1 至 n 的整数、 A 代表取代或未取代的 n 价碳环芳香环或杂环芳香环，以及 B1 至 Bn 各自独立地代表取代或未取代的碳环芳香基团或杂环芳香基团。
• Stabilizing Gold Adatoms by Thiophenyl Derivatives: A Possible Route toward Metal Redispersion
  作者：Bing Yang、Yi Pan、Xiao Lin、Niklas Nilius、Hans-Joachim Freund、Catherine Hulot、Anne Giraud、Siegfried Blechert、Sergio Tosoni、Joachim Sauer

  DOI：10.1021/ja300304s

  日期：2012.7.11

  Tris(phenylthio)benzene molecules have been synthesized in order to explore their ability to trap single Au adatoms on an Au(111) surface. The resulting metal organic complexes have been characterized with low-temperature scanning tunneling microscopy and infrared reflection absorption spectroscopy; possible structure models have been derived from density functional calculations. Upon room temperature deposition, the thiophenyl derivatives form dimer structures, comprising two molecules and six Au adatoms. Below 100 K, isolated molecules are found as well that have trapped up to six Au atoms. On the basis of the experimental results and calculated formation energies of the complexes, we discuss potential applications of the thioethers for the redispersion of metals on a catalyst surface. First experiments performed on Au particle ensembles prepared on alumina thin films suggest that the molecular ligands are indeed able to change the distribution of gold on the oxide surface.
• Synthesis of Di-, Tri-, and Tetrasulfides through Multifold Carbon−Sulfur Cross-Coupling Reactions with Indium Tri(organothiolates) in a One-Pot Procedure
  作者：Phil Ho Lee、Youngchul Park、Sangkyun Park、Euijae Lee、Sunggak Kim

  DOI：10.1021/jo102441t

  日期：2011.2.4

  Pd-catalyzed multifold (2-, 3-, and 4-fold) carbon sulfur cross-coupling reaction of indium tri(organothiolates) with polybromonated aromatic and heteroaromatic compounds was developed in a one-pot procedure. Both 2,5-dibromopyridine and 2,6-dibromopyridine reacted with indium tri(organothiolates) (0.68 equiv) in the presence of 4 mol A of Pd(OAc)(2), 4.2 mol % of Xantphos, and 1 equiv of diisopropylethylamine (DIPEA), producing disulfides in good to excellent yields. These results indicate that indium tri(organothiolates) transfer all three alkyl- or arylthio groups attached to indium metal to electrophilic coupling partners. Indium tri(organothiolates) derived from alkyl thiol having a low boiling point, such as n-propyl, isopropyl, and tert-butyl thiol, acted as good nucleophilic coupling partners. In addition, indium tri(arylthiolates) derived from aryl thiols possessing an electron-withdrawing or -donating group on the aromatic ring participated well in the Pd-catalyzed multifold carbon sulfur cross-coupling reaction. 4,4'-Dibromo-1,1'-biphenyl, 9,10-dibromoanthracene, 2,4-dibromoanisole, 2,7-dibromo-9,9-dimethylfluorene, 3,4-dibromothiophene, 2,3-dibromothiophene, 2,2'-bithiophene, 1,3,5-tribromobenzene, and 1,2,4,5-tetrabromobenzene were converted smoothly to the corresponding di-, tri-, and tetrasulfides.