1-methylsulfanyl-4-(4-bromophenylsulfanyl)-benzene | 203631-72-5

• 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-methylsulfanyl-4-(4-bromophenylsulfanyl)-benzene
• 英文别名: (4-bromophenyl)(4-methylthiophenyl)thioether；1-Bromo-4-(4-methylsulfanylphenyl)sulfanylbenzene；1-bromo-4-(4-methylsulfanylphenyl)sulfanylbenzene
• CAS: 203631-72-5
• 化学式: C₁₃H₁₁BrS₂
• 分子量: 311.266
• InChiKey: KDZRSEVIIVAOBB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  50.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-methylsulfanyl-4-(4-bromophenylsulfanyl)-benzene 在 Pd-catalyst 2-丙烷硫醇钠 作用下， 生成 4-[4-(4-Propan-2-yloxyphenyl)sulfanylphenyl]sulfanylbenzenethiol
  参考文献：
  名称：

  Synthesis ofp-Phenylene Sulfide Molecular Asterisks

  摘要：

  具有芳香族中心核心(部分能够发出荧光)的“超巨星”是通过将侧臂高效连接到核心而合成的，采用的是MacNicol反应。根据侧臂前体的长度，可获得第二代、第三代(文中所示)或第四代分子星；当苯环核心被冠状烯取代时，能够制得具有12条侧臂的分子星。

  DOI：

  10.1002/(sici)1521-3773(19981204)37:22<3149::aid-anie3149>3.0.co;2-4
• 作为产物：
  描述：

  4-溴茴香硫醚 在 喹啉 、 溴 、 溶剂黄146 作用下， 反应 9.0h， 生成 1-methylsulfanyl-4-(4-bromophenylsulfanyl)-benzene
  参考文献：
  名称：

  Synthesis and Properties of Water-Soluble Asterisk Molecules

  摘要：

  An asterisk is comprised of six semirigid arms projecting from a benzene nucleus. In the case at hand, asterisks were synthesized with one, two, or three aromatic rings (connected by sulfur atoms) in each of the six arms. A phosphomonoester at the termini of each arm solubilized the asterisks in water. The colloidal properties of these amphiphilic molecules were investigated by UV-vis and fluorescence spectroscopy, calorimetry, light scattering, surface tensiometry, and pulse-gradient spin-echo NMR. Solubility, solubilization, metal binding, and micelle "seeding" experiments were also carried out. Chain-conformation and supramolecular assembly into remarkable molecular "scrolls" were investigated by X-ray analysis and electron microscopy, respectively. One of the more interesting properties of the asterisks is that they remain monomeric in water despite having as many as 19 hydrophobic aromatic rings exposed to the water. The reasons for this behavior, and the possibility of exploiting it for constructing enzyme models free from aggregation equilibria, are discussed.

  DOI：

  10.1021/ja0206238

文献信息

• Functionalized p-phenylene sulfides Synthesis of new molecular wires
  作者：Alain Pinchart、Carol Dallaire、Marc Gingras

  DOI：10.1016/s0040-4039(97)10624-4

  日期：1998.2

  Molecular wires containing p-phenylene sulfide units were synthesized. They could be used in material sciences and in supramolecular chemistry. Wires having 2 to 6 phenyl rings were functionalized at one end by an SH or Sh-le group, and at the other end, by an OH, OMe or OiPr groups. Formation of Ar-S bonds in the chain was achieved by Pd- or Cu-catalyzed couplings of aromatic thiols with aromatic halides. Conditions for a clean chemoselective deprotection of thiols from thiomethyl groups were developed. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
• 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.
• Synthesis and Properties of Water-Soluble Asterisk Molecules
  作者：Fredric M. Menger、Vladimir A. Azov

  DOI：10.1021/ja0206238

  日期：2002.9.1

  An asterisk is comprised of six semirigid arms projecting from a benzene nucleus. In the case at hand, asterisks were synthesized with one, two, or three aromatic rings (connected by sulfur atoms) in each of the six arms. A phosphomonoester at the termini of each arm solubilized the asterisks in water. The colloidal properties of these amphiphilic molecules were investigated by UV-vis and fluorescence spectroscopy, calorimetry, light scattering, surface tensiometry, and pulse-gradient spin-echo NMR. Solubility, solubilization, metal binding, and micelle "seeding" experiments were also carried out. Chain-conformation and supramolecular assembly into remarkable molecular "scrolls" were investigated by X-ray analysis and electron microscopy, respectively. One of the more interesting properties of the asterisks is that they remain monomeric in water despite having as many as 19 hydrophobic aromatic rings exposed to the water. The reasons for this behavior, and the possibility of exploiting it for constructing enzyme models free from aggregation equilibria, are discussed.
• Synthesis ofp-Phenylene Sulfide Molecular Asterisks
  作者：Marc Gingras、Alain Pinchart、Carol Dallaire

  DOI：10.1002/(sici)1521-3773(19981204)37:22<3149::aid-anie3149>3.0.co;2-4

  日期：1998.12.4

  "Megastars" with aromatic central cores, some of which fluoresce, were synthesized by the efficient connection of the side arms to the core by using the MacNicol reaction. Depending on the length of the side arm precursor, second-, third- (depicted), or fourth-generation molecular asterisks were obtained; a twelve-armed molecular asterisk was prepared when the benzene core was replaced by a coronene one.

  具有芳香族中心核心(部分能够发出荧光)的“超巨星”是通过将侧臂高效连接到核心而合成的，采用的是MacNicol反应。根据侧臂前体的长度，可获得第二代、第三代(文中所示)或第四代分子星；当苯环核心被冠状烯取代时，能够制得具有12条侧臂的分子星。