(4-iodophenyl)(4-methoxyphenyl)thioether | 861083-81-0

• 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-iodophenyl)(4-methoxyphenyl)thioether
• 英文别名: 4-((4-iodophenyl)thio)benzonitrile；(4-iodophenyl)(4-methoxyphenyl)sulfane；1-(4-iodo-phenylsulfanyl)-4-methoxy-benzene；(4-Jod-phenyl)-(4-methoxy-phenyl)-sulfid；1-(4-Jod-phenylmercapto)-4-methoxy-benzol；1-Iodo-4-(4-methoxyphenyl)sulfanylbenzene
• CAS: 861083-81-0
• 化学式: C₁₃H₁₁IOS
• 分子量: 342.2
• InChiKey: UCPLABRBPDHMPY-UHFFFAOYSA-N

物化性质

• 熔点：
  102 °C
• 沸点：
  202-205 °C(Press: 2-4 Torr)
• 密度：
  1.65±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 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：
  34.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (4-iodophenyl)(4-methoxyphenyl)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 96.0h， 生成 ((4-methoxyphenylthio)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
• 作为产物：
  描述：

  4-((4-methoxyphenyl)thio)aniline 在 盐酸 、 potassium iodide 作用下， 生成 (4-iodophenyl)(4-methoxyphenyl)thioether
  参考文献：
  名称：

  US2065808

  摘要：

  公开号：

文献信息

• Copper-Catalyzed Sulfenylation of Boronic Acids with Sulfonyl Hydrazides
  作者：Ting-Ting Wang、Fu-Lai Yang、Shi-Kai Tian

  DOI：10.1002/adsc.201400995

  日期：2015.3.23

  bonds has been developed using sulfonyl hydrazides as sulfenyl sources. A range of sulfonyl hydrazides underwent tetrakis(acetonitrile)copper(I) tetrafluoroborate [Cu(CH3CN)4BF4]/2,2′‐bipyridine‐catalyzed sulfenylation with boronic acids under air to give structurally diverse thioethers in moderate to good yields. Preliminary mechanistic studies show that sulfonyl hydrazides are subjected to decomposition

  使用磺酰肼作为亚磺酰基来源，已经开发出前所未有的碳-硼键亚磺酰化反应。一系列磺酰肼在空气中进行了四氟硼酸四（乙腈）铜（I）四氟硼酸酯[Cu（CH 3 CN）4 BF 4 ] / 2,2'-联吡啶催化的亚硼酸酯化，得到结构多样的硫醚，中等至良好产量。初步的机理研究表明，磺酰肼会分解为硫代磺酸盐和二硫化物，然后与硼酸形成碳硫键。
• Synthesis of molecular chains: application of cross-coupling and bromo by iodo exchange reactions
  作者：Jesús M. Fernández-Hernández、Verónica Cámara、José Vicente

  DOI：10.1016/j.tet.2015.06.072

  日期：2015.8

  The synthesis of a series of molecular chains by use of C–S, C–N and C-Alkyne cross coupling, as well as bromo by iodo exchange reactions, has been reported. Two different types of chains R–C6H4–S–C6H4–CC–C6H4–NH–C6H4–Br, and R–C6H4–S–C6H4–NH–C6H4–CC–C6H4–Br (R=MeO, CN, NO2) could be obtained starting from the same thioether but applying different reaction sequences. Compounds R–C6H4–CC–C6H4–S–C6H4–NH–C6H4–Br

  据报道，通过使用C–S，C–N和C-炔烃交叉偶联以及溴的碘交换反应，可以合成一系列分子链。两种不同类型的链R–C 6 H 4 –S–C 6 H 4 –C C–C 6 H 4 –NH–C 6 H 4 –Br和R–C 6 H 4 –S–C 6 H 4 –NH–C 6 H 4 –C C–C 6 H 4 –Br（R = MeO，CN，NO 2可以从相同的硫醚开始，但应用不同的反应顺序获得。化合物R–C 6 H 4 –C C–C 6 H 4 –S–C 6 H 4 –NH–C 6 H 4 –Br是由二芳基乙炔经碘代取代后与C–S和a交替生成的，由二芳基乙炔制得。 C–N交叉耦合。
• Palladium-Catalyzed Oxidative Cross-Coupling of Arylhydrazines and Arenethiols with Molecular Oxygen as the Sole Oxidant
  作者：Changliu Wang、Zhenming Zhang、Yongliang Tu、Ying Li、Jiale Wu、Junfeng Zhao

  DOI：10.1021/acs.joc.7b02926

  日期：2018.2.16

  A highly efficient palladium-catalyzed oxidative cross-coupling of arylhydrazines and arenethiols with molecular oxygen as the sole oxidant to afford unsymmetrical diaryl sulfides has been developed. The only byproducts are nitrogen and water. A broad range of functional groups, even the reactive iodides, are tolerated and thus offer the opportunity for further functionalization.

  已经开发出一种高效的钯催化芳基肼和芳硫醇与分子氧作为唯一氧化剂的氧化交叉偶联反应，可制得不对称的二芳基硫醚。唯一的副产物是氮气和水。宽泛的官能团，甚至是反应性碘化物，都是可以耐受的，因此为进一步官能化提供了机会。
• Hemin‐Promoted Direct C−H Thiolation in the Synthesis of Diaryl Sulfides
  作者：Bao Li、Junrui Wang、Guangliang Tu、Guodong Ju、Kehan Zhou、Yingsheng Zhao

  DOI：10.1002/ejoc.202201458

  日期：2023.3.21

  A new method for direct preparation of diphenyl sulfides using P-toluenesulfonyl chloride as an effective thiophenyl radical precursor with assistance from Hemin. Various substituted anisoles and benzenesulfonyl chlorides are well tolerated. Gram scale reactions showed a satisfactory performance, demonstrating the potential synthetic application of this method.

  以对甲苯磺酰氯为有效的噻吩自由基前驱体，氯化血红素辅助直接制备二苯硫醚的新方法。各种取代苯甲醚和苯磺酰氯耐受性良好。克级反应表现出令人满意的性能，证明了该方法的潜在合成应用。
• THE SYNTHESIS OF SOME IODATED DIPHENYL-SULFIDE PHENOLS¹
  作者：Shailer L. Bass、Treat B. Johnson

  DOI：10.1021/ja01366a050

  日期：1930.3