2-(trimethylsilyl)ethyl-4’-ethynylphenyl sulfide | 221292-45-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-(trimethylsilyl)ethyl-4’-ethynylphenyl sulfide
• 英文别名: 2-(trimethylsilyl)ethyl-4'-(ethynyl)phenyl sulfide；2-(trimethylsilyl)ethyl-4-(ethynyl)phenyl sulphide；{2-[(4-ethynylphenyl)thio]ethyl}trimethylsilane；HCC-C6H4-S-trimethylsilylethylene；Silane, [2-[(4-ethynylphenyl)thio]ethyl]trimethyl-；2-(4-ethynylphenyl)sulfanylethyl-trimethylsilane
• CAS: 221292-45-1
• 化学式: C₁₃H₁₈SSi
• 分子量: 234.437
• InChiKey: IFHRPEWVHSRBAS-UHFFFAOYSA-N

物化性质

• 沸点：
  298.4±25.0 °C(Predicted)
• 密度：
  0.97±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  2-(trimethylsilyl)ethyl-4’-ethynylphenyl sulfide 在 copper diacetate 作用下， 以 吡啶 为溶剂， 反应 46.0h， 以83%的产率得到1,4-bis(4-(2-(trimethylsilyl)ethylthio)phenyl)buta-1,3-diyne
  参考文献：
  名称：

  与三锇-羰基簇配位的丁二炔官能化配体的分子内环化

  摘要：

  二炔与[Os3(CO)11(CH3CN)]在水存在下的反应形成了有趣的氢化物三锇簇[Os3(μ-H)(CO)9{μ3,η1:η3:η1-RC2COHC ≡CR}] (1a–1c) 在温和条件下高产。当这些烯丙醇化合物 1a-1c 溶解在干燥的极性和供体溶剂中时，会发生分子内环化过程，得到 [Os3(μ-H)(CO)9{μ3,η1:η3:η1-RC2CH=COCR}] (2a-2c) 定量收率。利用[Os3(CO)11(CH3CN)]作为起始原料并加入水可以替代[Os3(μ-H)2(CO)10]的不便使用。这种合成方法为二炔环化提供了一种简便的途径，并且与迄今为止文献中描述的方法相比具有明显的优势。此外，类似的环化混合金属络合物 [Os3(μ-H)(CO)9{μ3,η1:η3:

  DOI：

  10.1002/zaac.201600229
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl-4'-bromophenyl sulfide 在 甲醇 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 potassium carbonate 、 二乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 生成 2-(trimethylsilyl)ethyl-4’-ethynylphenyl sulfide
  参考文献：
  名称：

  Enhanced Separation Concept (ESC)：通过分子设计从电极上去除功能亚基

  摘要：

  使用电场触发的 FeIIbis-三联吡啶复合物在机械控制的断裂连接实验中作为模型系统，提出了一种提高功能性单分子连接可靠性的新概念。该复合物包含一个推挽配体，可感应施加的 E 场，并且由此产生的 FeII 配体场的畸变预计会触发自旋交叉事件，反映在传输电流的突然跳跃中。通过分子工程，复合物的活性中心与金电极分离，以消除不需要的副作用。考虑两个方面来隔离中心金属离子，即通过引入额外的炔烃的间距和通过庞大的异丙基实现的空间屏蔽。有了这个小系列的模型复合体，

  DOI：

  10.1002/ejoc.201900432

文献信息

• Sulfide-capped wire-like metallaynes as connectors for Au nanoparticle assemblies
  作者：Jie-Wen Ying、David R. Sobransingh、Guo-Lin Xu、Angel E. Kaifer、Tong Ren

  DOI：10.1039/b412336k

  日期：——

  A new series of Ru2(DMBA)4(oligo(phenyleneethyne))2 compounds bearing sulfide termini was synthesized; structural characterization revealed both the rigid rod nature and extended π-conjugation in these metallaynes; in the presence of these metallaynes, Au nanoparticles readily assembled into dimers and chains with well-defined inter-dimer distances.

  合成了一系列新的Ru2(DMBA)4(oligo(phenyleneethyne))2化合物，具有硫化物末端；结构表征揭示了这些金属炔的刚性棒状特性和扩展的π共轭；在这些金属炔的存在下，金纳米颗粒容易组装成具有明确的二聚体间距的二聚体和链。
• Synthesis and characterization of wire-like Ru2(ap)4-[σ-oligo(phenylene ethynyl)] compounds
  作者：Tong Ren、Damon A. Parish、Guo-Lin Xu、Martin H. Moore、Jeffrey R. Deschamps、Jie-Wen Ying、Steven K. Pollack、Terence L. Schull、Ranganathan Shashidhar

  DOI：10.1016/j.jorganchem.2005.07.057

  日期：2005.11

  Reported herein are the synthesis, electrochemical and structural characterization of wire-like Ru2-alkynyl compounds, Ru2(ap)4(Ln)x, where ap is 2-anilinopyridinate, and Ln is –(CCC6H4)nSCH2CH2SiMe3 with n = 1 (1) and 2 (2), and x can be 1 (a) and 2 (b). Reactions between Ru2(ap)4Cl and one equiv. of LiLn yielded the mono-alkynyl compound only, while the use of 4–5 equiv. of LiLn resulted in a mixture

  本文报道的是线状Ru 2-炔基化合物Ru 2（ap）4（L n）x的合成，电化学和结构表征，其中ap是2-苯胺基吡啶鎓，L n是–（CCC 6 H 4）ñ SCH 2 CH 2森达3与ñ  = 1（1）和2（2），和X可以是1（一）和2（b）。Ru 2（ap）4 Cl和1当量。LiL n的使用仅产生单炔基化合物，而使用4-5当量。LiL n的得到导致单炔基和双炔基两者的混合物。化合物1a和1b的单晶X射线衍射研究表明，其结构与Ru 2（ap）4（C 2 Ph）和Ru 2（ap）4（C 2 Ph）2相似。， 分别。磁性，光谱和伏安测量还显示，由于带有硫醇-TMSE基团（–SCH 2 CH 2 SiMe 3）的OPE配体的功能化，对电子结构的干扰最小。最显著，它可以基于的结构来估计1A，在Ru的OPE2-S-键2A是显著长于C11硫醇SAM的深度，从而使得能够插入图2a到后者。
• Avoiding problem reactions at the ferrocenyl-alkyne motif: a convenient synthesis of model, redox-active complexes for molecular electronics
  作者：Michael S. Inkpen、Andrew J. P. White、Tim Albrecht、Nicholas J. Long

  DOI：10.1039/c4dt02359e

  日期：——

  A much improved route to 1,1′-bis(arylethynyl)ferrocenes comprising accessible thiolates on the aryl ring is reported. Unanticipated reactions between AcCl, TBAF–BBr₃ and ferrocenyl-alkynes are also discussed, offering a rationale for previous synthetic difficulties.

  报道了一种大大改进的合成1,1'-双(芳基乙炔基)二茂铁的路线，其中芳基环上有易获取的巯基。还讨论了AcCl、TBAF-BBr3和二茂铁基炔烃之间意想不到的反应，为以前的合成困难提供了合理解释。
• The synthesis of bis(oligophenyleneethynylenes): novel potential nonlinear optical materials
  作者：David J. Armitt、Geoffrey T. Crisp

  DOI：10.1016/j.tet.2005.11.015

  日期：2006.2

  Various functionalised phenyleneethynylene dimers 10 and trimers 12 were synthesised by palladium-catalyzed Sonogashira methodology. These dimers and trimers were coupled to 1,8-diido-10-methoxyanthracene to generate bis(oligophenyleneethynylenes) 17 and 18. Preliminary results towards the construction of both phenyleneethynylene and phenylenevinylene hybrid motifs are presented. (c) 2005 Elsevier Ltd. All rights reserved.
• Characterization of Self-Assembled Monolayers of Fullerene Derivatives on Gold Surfaces:  Implications for Device Evaluations
  作者：Yasuhiro Shirai、Long Cheng、Bo Chen、James M. Tour

  DOI：10.1021/ja063451d

  日期：2006.10.1

  The widely employed approach to self-assembly of fullerene derivatives on gold can be complicated due to multilayer formations and head-to-tail assemblies resulting from the strong fullerene-fullerene and fullerene-gold interactions. These anomalies were not examined in detail in previous studies on fullerene self-assembled monolayers (SAMs) but were clearly detected in the present work using surface characterization techniques including ellipsometry, cyclic voltammetry (CV), and X-ray photoelectron spectroscopy (XPS). This is the first time that SAMs prepared from fullerene derivatives of thiols/thiol esters/disulfides have been analyzed in detail, and the complications due to multilayer formations and head-to-tail assemblies were revealed. Specifically, we designed and synthesized several fullerene derivatives based on thiols, thiol acetates, and disulfides to address the characterization requirements, and these are described and delineated. These studies specifically address the need to properly characterize and control fullerene-thiol assemblies on gold before evaluating subsequent device performances.