((4-nitrophenylthio)phenyl)((4-bromophenylthio)phenyl)thioether | 865179-29-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: ((4-nitrophenylthio)phenyl)((4-bromophenylthio)phenyl)thioether
• 英文别名: 1-[4-[4-(4-Bromophenyl)sulfanylphenyl]sulfanylphenyl]sulfanyl-4-nitrobenzene；1-[4-[4-(4-bromophenyl)sulfanylphenyl]sulfanylphenyl]sulfanyl-4-nitrobenzene
• CAS: 865179-29-9
• 化学式: C₂₄H₁₆BrNO₂S₃
• 分子量: 526.499
• InChiKey: XBGVGCXAIJNWTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  31
• 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：
  122
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ((4-nitrophenylthio)phenyl)((4-bromophenylthio)phenyl)thioether 在 trans-N,N'-dimethyl-1,2-cyclohexyldiamine 、 1,1'-双(二苯基膦)二茂铁 、 copper(l) iodide 、 potassium tert-butylate 、 sodium iodide 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 72.0h， 生成 1-(4-nitrophenylthio)phenylthio-4-(4-bromophenylthio)phenylthio-benzene
  参考文献：
  名称：

  A new approach to the synthesis of oligomers. Application to the synthesis of p-phenylene thioether wires

  摘要：

  Oligothioethers 4-RC6H4(SC6H4-4)(n)X (n = 1-3; X = Br, I; R = NO2; X = Br; R = MeO. n = 1 and 2; X = I; R = MeO. n = 4; X = Br; R = NO2) have been prepared through a process involving (i) palladium-catalyzed C-S coupling between 4-RC6H4(SC6H4-4),(n-1) and 4-BrC6H4SH to give 4-RC6H4(SC6H4-4)(n) Br and (ii) copper-catalyzed replacement of Br by I. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.143
• 作为产物：
  描述：

  1-(4-溴苯基)硫烷基-4-硝基苯 在 trans-N,N'-dimethyl-1,2-cyclohexyldiamine 、 1,1'-双(二苯基膦)二茂铁 、 copper(l) iodide 、 potassium tert-butylate 、 sodium iodide 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 144.0h， 生成 ((4-nitrophenylthio)phenyl)((4-bromophenylthio)phenyl)thioether
  参考文献：
  名称：

  A new approach to the synthesis of oligomers. Application to the synthesis of p-phenylene thioether wires

  摘要：

  Oligothioethers 4-RC6H4(SC6H4-4)(n)X (n = 1-3; X = Br, I; R = NO2; X = Br; R = MeO. n = 1 and 2; X = I; R = MeO. n = 4; X = Br; R = NO2) have been prepared through a process involving (i) palladium-catalyzed C-S coupling between 4-RC6H4(SC6H4-4),(n-1) and 4-BrC6H4SH to give 4-RC6H4(SC6H4-4)(n) Br and (ii) copper-catalyzed replacement of Br by I. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.06.143

文献信息

• Synthesis of molecular chains: phenylene thioether and sulfoxide oligomers
  作者：José Vicente、José A. Abad、Rosa M. López-Nicolás

  DOI：10.1016/j.tet.2008.04.108

  日期：2008.6

  The application of a general synthetic approach to prepare molecular chains is reported. It is based on a step-by-step method each consisting first in a Pd-catalyzed reaction between ArI and HXAr'Br (Ar=aryl, Ar'=arylene) to give ArXAr'Br followed by a Cu-catalyzed replacement of Br by I to give ArXAr'I that can be reacted with HXAr'Br in the following step. The application of this method is here illustrated to prepare phenylene sulfide oligomers (X=S). Starting from RC6H4I-4 (R=H, MeO, NO2, NH2) and HSC6H4BF-x (x=2, 4) it is possible to grow chains in one direction to give X(C6H4S-m)(n)C6H4R-4 (n=1, X=Br, m=4, R=H, MeO, NO2, NH2, SMe and m=2, R=H, MeO, NO2; n=1, X=I, m=2 or 4, R=H, MeO, NO2; n=2, X=Br, m=2 or 4, R=H, MeO, NO2; n=2, X=I, m=4, R=MeO, NO2; n=3, X=Br, m=4, R=MeO, NO2; n=3, X=I, m=4, R=NO2 and n=4, X=Br or I, m=4, R=NO2). From HSC6H4Br-x and IC6H4I-4 the chains can grow in two directions to give X(C6H4S-4)(n)C6H4X-4 (n=2 or 4, X=Br or I), 2-XC6H4(SC6H4-4)(n)SC6H4X-2 (n=3 or 5, X=Br). Using diiodomesitylene the dithioethers C6HMe3-2,4,6-(SC6H4X-4)(2)-1,3 (X=Br, I) have been prepared. The series of sulfoxides X(C6H4S(O)-4)(n)C6H4R-4 (X=Br, n=1, R=MeO, n=3, R=NO2, n=4, R=Br; X=R=I, n=2) has been obtained from the corresponding thioethers and PhICl2. (C) 2008 Elsevier Ltd. All rights reserved.
• A new approach to the synthesis of oligomers. Application to the synthesis of p-phenylene thioether wires
  作者：José Vicente、José A. Abad、Rosa M. López-Nicolás

  DOI：10.1016/j.tetlet.2005.06.143

  日期：2005.8

  Oligothioethers 4-RC6H4(SC6H4-4)(n)X (n = 1-3; X = Br, I; R = NO2; X = Br; R = MeO. n = 1 and 2; X = I; R = MeO. n = 4; X = Br; R = NO2) have been prepared through a process involving (i) palladium-catalyzed C-S coupling between 4-RC6H4(SC6H4-4),(n-1) and 4-BrC6H4SH to give 4-RC6H4(SC6H4-4)(n) Br and (ii) copper-catalyzed replacement of Br by I. (c) 2005 Elsevier Ltd. All rights reserved.