1-bromo-4-(dodecylsulfanyl)benzene | 129476-49-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 1-bromo-4-(dodecylsulfanyl)benzene
• 英文别名: (4-bromophenyl)(dodecyl)sulfane；1-(4-Bromophenylthio)dodecane；1-bromo-4-dodecylsulfanylbenzene
• CAS: 129476-49-9
• 化学式: C₁₈H₂₉BrS
• 分子量: 357.398
• InChiKey: PJLGRZLEESDJEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.7
• 重原子数：
  20
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  25.3
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-bromo-4-(dodecylsulfanyl)benzene 在 碘 、 magnesium 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 为溶剂， 反应 19.0h， 生成
  参考文献：
  名称：

  丙二酸酯与α,β-不饱和醛的环保不对称有机催化共轭加成：在手性吲哚合成中的应用

  摘要：

  目前，合成社区面临着解决日益增长的环境问题的需要。为了减少有机转化对环境的影响，所有传统的合成方法，包括不对称合成方案，都应该进行审查，如果可能的话，由继续满足效率、选择性需求的新工艺取代，但对环境无害。

  DOI：

  10.1002/ejoc.201300431
• 作为产物：
  描述：

  对溴碘苯 、 十二硫醇 在 Cu/Al₂O₃ 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.5h， 以70%的产率得到1-bromo-4-(dodecylsulfanyl)benzene
  参考文献：
  名称：

  硫醇与芳基卤化物的可循环异构负载的铜催化偶联：溴代碘代苯的碱控制的差分芳硫醇化

  摘要：

  氧化铝负载的硫酸铜可在无氧，无配体的条件下，有效地催化芳基，杂芳族和脂肪族硫醇与芳基以及杂芳基卤化物的S-芳基化反应。该协议通过在芳香族卤化物中通过硫醇与碘代和溴代取代基的碱基控制的差分偶联，轻松获得各种硫醚以及不对称的双硫醚。该催化剂便宜，对空气不敏感，环境友好且可回收。

  DOI：

  10.1002/adsc.200900358

文献信息

• Recyclable Heterogeneous Supported Copper-Catalyzed Coupling of Thiols with Aryl Halides: Base-Controlled Differential Arylthiolation of Bromoiodobenzenes
  作者：Sukalyan Bhadra、Bojja Sreedhar、Brindaban C. Ranu

  DOI：10.1002/adsc.200900358

  日期：2009.10

  Alumina-supported copper sulfate efficiently catalyzes the S-arylation of aromatic, heteroaromatic and aliphatic thiols with aryl as well as heteroaryl halides under aerobic, ligand-free conditions. This protocol provides an easy access to a variety of thioethers as well as unsymmetrical bis-thioethers by base-controlled differential coupling of thiols with iodo- and bromo-substituents in an aromatic

  氧化铝负载的硫酸铜可在无氧，无配体的条件下，有效地催化芳基，杂芳族和脂肪族硫醇与芳基以及杂芳基卤化物的S-芳基化反应。该协议通过在芳香族卤化物中通过硫醇与碘代和溴代取代基的碱基控制的差分偶联，轻松获得各种硫醚以及不对称的双硫醚。该催化剂便宜，对空气不敏感，环境友好且可回收。
• Organocatalytic asymmetric epoxidation and tandem epoxidation/Passerini reaction under eco-friendly reaction conditions
  作者：Anna Maria Deobald、Arlene G. Corrêa、Daniel G. Rivera、Márcio Weber Paixão

  DOI：10.1039/c2ob26247a

  日期：——

  An eco-friendly synthesis of highly functionalized epoxides and their incorporation into an organocatalytic multicomponent approach are reported. For this, a modified class of diarylprolinol silyl ethers was designed to enable high catalytic activity in an environmentally benign solvent system. The one-pot procedure showed great efficiency in promoting stereoselective multicomponent transformations in a tandem, ‘green’ fashion. Because of its non-residual, efficient and selective character, this synthetic design shows promise for large-scale applications in both diversity and target-oriented syntheses.

  报道了一种环保的高功能化环氧化物合成方法，并将其应用于有机催化多组分反应策略。为此，设计了一类改良的二芳基脯氨醇硅醚，以在环境友好的溶剂体系中实现高催化活性。该一步法程序非常有效，能够促进立体选择性多组分反应以连贯、环保的方式进行。由于其无残留、高效和选择性的特点，这种合成设计在多样的和目标导向的合成中具有大规模应用的潜力。
• Syntheses of Aryl Thioethers <i>via</i> Aromatic Substitution of Aryl Halides at 0 to 25 °C
  作者：Marina Tsuzaki、Shin Ando、Tadao Ishizuka

  DOI：10.1248/cpb.c23-00232

  日期：2023.7.1

  In this study, we developed mild conditions for the synthesis of an aryl thioether via aromatic substitution using aryl halides, which is a process that has rarely been studied. Aromatic substrates such as aryl fluorides activated with a halogen substituent are difficult to use for substitution reactions, but by using 18-crown-6-ether as an additive, these were successfully converted to their corresponding

  在这项研究中，我们开发了使用芳基卤通过芳族取代合成芳基硫醚的温和条件，这是一个很少被研究的过程。芳香族底物如用卤素取代基活化的芳基氟化物很难用于取代反应，但通过使用18-冠-6-醚作为添加剂，这些被成功转化为相应的硫醚产物。在我们建立的条件下，除了多种硫醇外，毒性较小、无味的二硫化物也可以在0至25°C下直接用作亲核试剂。 全尺寸图像
• A general rhodium-catalyzed cross-coupling reaction of thiols with aryl iodides
  作者：Chih-Shin Lai、Hsin-Lun Kao、Yan-Jhang Wang、Chin-Fa Lee

  DOI：10.1016/j.tetlet.2012.06.054

  日期：2012.8

  The general procedure for the rhodium-catalyzed cross-coupling of thiols with aryl iodides is described. The catalytic system consists of 5 mol % of [RhCl(cod)](2) and 10 mol % of PPh3 as a ligand. A variety of aryl iodides reacted with thiols, giving aryl thioethers in good to excellent yields. It is important to note that the deactivated aryl iodides such as 4-iodoanisole is worked smoothly to provide the corresponding aryl thioethers in excellent yields. Functional groups such as free-amines, chloro, are all tolerated under the employed reaction conditions. (C) 2012 Elsevier Ltd. All rights reserved.
• Enhanced Aggregation of Derivatized Tolan Surfactants through Donor−Acceptor Interactions at the Air−Water Interface and in Langmuir−Blodgett Films
  作者：Catie Weiss Farahat、Thomas L. Penner、Abraham Ulman、David G. Whitten

  DOI：10.1021/jp960579g

  日期：1996.1.1

  Control of aggregation behavior of derivatized surfactants by moderately polar functional groups as well as the role of charge-transfer interactions governing photophysical phenomena was studied using surfactants incorporating the diphenylacetylene (tolan) chromophore (TFAs) modified with either a sulfone or an ether group (sTA or oTA, respectively). H aggregation is prevalent in these systems as monitored by the spectral shifts of absorption and emission. Packing of surfactants and aggregation were found to be strongly influenced by the presence of bivalent metal cations, Cd2+, in the subphase, as demonstrated by molecular area and chain orientation measurements. The nature of the aggregates formed from sTA surfactants is directly affected by complexation of the acid headgroup; in contrast, the associated oTA chromophore aggregation is unaffected by subphase modifications, despite the altered packing of surfactant chains. The photophysical behavior of aggregated TFAs in monolayer systems was followed at the air-water interface as well as with supported films on quartz, and conclusions can be made of the surfactant arrangements' stability. A unique mixed aggregate was formed when both the ether- and sulfone-derivatized TFAs were incorporated into a single phosphatidylcholine molecule (mixed PC) and deposited as an LB film. This monolayer exhibits additional enhancement in aggregation properties attributed to donor-acceptor interactions between the tolan chromophores that are distinct from a statistically mixed LB sample prepared from a mixture of TFAs. The current results are viewed in terms of general principles governing aggregation for a family of chromophore-derivatized surfactants in LB film.