(2-碘苯基)(苯基)硫醚 | 2236-42-2

• 物质功能分类: 有机原料 - 烃类化合物及其衍生物 - 芳香烃
• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 中文名称: (2-碘苯基)(苯基)硫醚
• 英文名称: (2-iodophenyl)(phenyl)sulfane
• 英文别名: 2-iodophenyl phenyl sulfide；1-iodo-2-phenylsulfanylbenzene
• CAS: 2236-42-2
• 化学式: C₁₂H₉IS
• 分子量: 312.174
• InChiKey: XFEBWRWHFLDLIY-UHFFFAOYSA-N

物化性质

• 熔点：
  52-53 °C
• 沸点：
  336.1±25.0 °C(Predicted)
• 密度：
  1.69±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2930909090

反应信息

• 作为反应物：
  描述：

  (2-碘苯基)(苯基)硫醚 在 tris-(dibenzylideneacetone)dipalladium(0) 、 copper diacetate 、 特戊酸钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以81%的产率得到二苯并噻吩
  参考文献：
  名称：

  Palladium Catalyzed Syntheses of Dibenzothiophenes by Ring-Closure of 2-Iodinated Diaryl Thioether

  摘要：

  An efficient ring-closure of 2-iodinated diaryl thioethers at the presence of palladium catalyst to form dibenzothiophene is described. After the best condition was set up as Pd-3(dba)(2) as the catalyst, anhydrous Cu(OAc)(2) as additive, PivONa center dot H2O as base, DMF as solvent, a series of dibenzothiophenes could be successfully obtained through this protocol in moderate to excellent yields.

  DOI：

  10.3987/com-16-13531
• 作为产物：
  描述：

  2-bromophenyl phenyl sulfide 在 copper(l) iodide 、 sodium iodide 作用下， 以 1,4-二氧六环 为溶剂， 反应 48.0h， 以85%的产率得到(2-碘苯基)(苯基)硫醚
  参考文献：
  名称：

  Synthesis of molecular chains: phenylene thioether and sulfoxide oligomers

  摘要：

  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.

  DOI：

  10.1016/j.tet.2008.04.108

文献信息

• [EN] 4-(2-PHENYLSULFANYL-PHENYL)-PIPERIDINE DERIVATIVES AS SEROTONIN REUPTAKE INHIBITORS<br/>[FR] DERIVES 4-(2-PHENYLSULFANYL-PHENYL)-PIPERIDINES UTILISES EN TANT QU'INHIBITEURS DE REABSORPTION DE LA SEROTONINE
  申请人：LUNDBECK & CO AS H

  公开号：WO2004087156A1

  公开（公告）日：2004-10-14

  The invention provides compounds represented by the general formula (I) wherein the substituents are defined in the application. The compounds are useful in the treatment of an affective disorder, including depression, anxiety disorders including general anxiety disorder and panic disorder and obsessive compulsive disorder.

  该发明提供了一种由一般公式（I）表示的化合物，其中取代基在申请中定义。这些化合物在治疗情感障碍方面具有用途，包括抑郁症、焦虑障碍（包括广泛性焦虑障碍和恐慌障碍）以及强迫症。
• Synthesis of mono- and trinuclear palladium(II) complexes via oxidative addition of a bulky hexathioether containing a disulfide bond to palladium(0)
  作者：Daisuke Shimizu、Nobuhiro Takeda、Norihiro Tokitoh

  DOI：10.1016/j.jorganchem.2006.10.056

  日期：2007.6

  The oxidative addition reactions of a bulky hexathioether containing a disulfide bond, TbtS(o-phen)S(o-phen)SS(o-phen)S(o-phen)STbt (1) (Tbt = 2,4,6-tris[bis(trimethylsilyl)methyl]phenyl, o-phen = o-phenylene), to a palladium(0) complex were studied. In the reaction of 1 with 3 molar amounts of [Pd(PPh3)4], a trinuclear palladium(II) complex, [Pd3S(o-phen)S}2(o-phen)STbt}2(PPh3)2] (2), was formed

  含有二硫键的大体积六硫醚TbtS（o -phen ）S（o -phen）SS（o -phen ）S（o -phen）STbt（1）的氧化加成反应（Tbt = 2,4,6-研究了三[双（三甲基甲硅烷基）甲基]苯基，邻-苯基= 邻-亚苯基）与钯（0）的配合物。在1与3摩尔量的[Pd（PPh 3）4 ]的反应中，三核钯（II）络合物[Pd 3 S（o -phen）S} 2 （o -phen）STbt} 2（ PPh 3）2 ]（2）是通过三步钯插入反应形成的，包括不寻常的C（芳基）–S键裂解。另一方面，1与等摩尔量的[Pd（PPh 3）4 ]反应得到具有伪八面体结构的单核钯（II）配合物，[Pd S（o- phen）S（o- phen） ）STbt} 2 ]（3）。钯原子在3中的六配位几何结构通过分子中的原子（AIM）分析得到证实，该分析揭示了中心Pd原子和S原子在轴向位置之间存在键临界点
• Structure and Reactivity of N‐Heterocyclic Alkynyl Hypervalent Iodine Reagents
  作者：Eliott Le Du、Thibaut Duhail、Matthew D. Wodrich、Rosario Scopelliti、Farzaneh Fadaei‐Tirani、Elsa Anselmi、Emmanuel Magnier、Jerome Waser

  DOI：10.1002/chem.202101475

  日期：2021.7.26

  Ethynylbenziodoxol(on)e (EBX) cyclic hypervalent iodine reagents have become popular reagents for the alkynylation of radicals and nucleophiles, but only offer limited possibilities for further structure and reactivity fine-tuning. Herein, the synthesis of new N-heterocyclic hypervalent iodine reagents with increased structural flexibility based on amide, amidine and sulfoximine scaffolds is reported

  乙炔苯并氧杂环戊烯 (EBX) 环状高价碘试剂已成为自由基和亲核试剂炔基化的常用试剂​​，但仅为进一步结构和反应性微调提供有限的可能性。在此，报道了基于酰胺、脒和亚砜亚胺支架的新型N-杂环高价碘试剂的合成，该试剂具有增加的结构灵活性。报告了试剂的固态结构，并且对 I−C炔键长度的分析允许评估不同取代基的反式效应。由 DFT 计算得出的试剂分子静电势 (MEP) 图揭示了磺酰胺基化合物不太明显的 σ 孔区域。大多数试剂在β-酮酯的炔基化反应中反应良好。硫醇的炔基化提供了更多的可变产率，具有更强σ-空穴的化合物反应更好。在金属介导的转化中，与 O 基 EBX 试剂相比，N-杂环高价碘试剂的结果较差。
• A mild and efficient SRN1 approach to diaryl sulfides from arenediazonium tetrafluoroborates
  作者：Giovanni Petrillo、Marino Novi、Giacomo Garbarino、Dell'erba Carlo

  DOI：10.1016/s0040-4020(01)87556-6

  日期：1986.1

  arenethlolates in Me2SO at 25°C represents an efficient access to diaryl sulfides. A number of evidences suggest the occurrence of a radical, radical-anion SRNl mechanism, the arenethlolate acting both as electron donor and as aryl-radical trapping nucleophile. Valuable improvements with respect to recent SRNl syntheses of diaryl sulfides from haloarenes are represented. Inter alia, by the compatibility

  在我四氟硼酸芳基重氮和钠arenethlolates之间的反应2 SO在25℃下表示对碳酸二芳基硫化物的高效访问。许多证据表明自由基，自由基阴离子S的发生RN升机构，所述arenethlolate既作为电子供体和作为芳基自由基捕获作用的亲核试剂。代表了相对于最近从卤代芳烃的S RN 1合成二芳基硫的有价值的改进。特别地，通过重氮和释放电子的取代基的相容性以及在重氮盐中对空间位阻的不敏感性。当芳烃二氮杂ion离子带有另一个S RN- 1的离去基团（例如Cl，Br或I）时，主要形成可破坏性产物。
• Properties modulation of organic semi-conductors based on a donor-spiro-acceptor (D-spiro-A) molecular design: new host materials for efficient sky-blue PhOLEDs
  作者：Maxime Romain、Denis Tondelier、Olivier Jeannin、Bernard Geffroy、Joëlle Rault-Berthelot、Cyril Poriel

  DOI：10.1039/c5tc01812a

  日期：——

  Four high triplet organic semi-conductors based on the donor-spiro-acceptor design (D-spiro-A) have been synthesized.

  基于给体-螺环-受体设计（D-spiro-A），已合成了四种高三重态有机半导体。