2-(三甲基甲硅烷基)-5-甲基噻吩 | 18387-92-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 中文名称: 2-(三甲基甲硅烷基)-5-甲基噻吩
• 英文名称: 2-methyl-5-(trimethylsilyl)thiophene
• 英文别名: trimethyl(5-methylthiophen-2-yl)silane；2-Methyl-5-trimethylsilyl-thiophen；2-(trimethylsilyl)-5-methylthiophene；trimethyl-(5-methylthiophen-2-yl)silane
• CAS: 18387-92-3
• 化学式: C₈H₁₄SSi
• 分子量: 170.351
• InChiKey: LYPIKOKEIPRFIW-UHFFFAOYSA-N

物化性质

• 沸点：
  101-102 °C(Press: 50 Torr)
• 密度：
  0.9274 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2-(三甲基甲硅烷基)-5-甲基噻吩 以 甲醇 、 高氯酸 为溶剂， 生成 2-甲基噻吩
  参考文献：
  名称：

  取代的2-三甲基甲硅烷基噻吩的甲硅烷基化

  摘要：

  在50℃下一级速率常数已被确定为的裂解噻吩化合物XC 4 ħ 2 S˙SiMe 3 -2（a）中的MeOH（5体积）用含水的HClO的混合物4（2体积）和（b）CH 3 CO 2 H（4体积）与H 2 SO 4水溶液（3体积）。在第一种介质中的相对比率k rel是（X =）5-OMe，7 200；5我，36; H，1.00； H，1.00。5-Cl，1.08×10 –1 ; 5-溴，9.0×10 -2 ; 3-溴，5.0×10 –2 ; 4-Br，4.9×10 –3，第二种介质，5-Me，36；H，1.00； H，1.00。5-Cl，1.28×10 –1；5-溴，9.8×10–2 ; 3-溴，5.5×10 –2 ; 4-溴，6.5×10 –3；5-NO 2，7.1×10 -7 ; 3-NO 2，7.1×10 -7。除了硝基化合物，两组日志ķ相对值示出与相应的XC的值良好的线性相关性6 ħ

  DOI：

  10.1039/p29810000931
• 作为产物：
  描述：

  2-甲基噻吩 、 三甲基氯硅烷 在 正丁基锂 作用下， 生成 2-(三甲基甲硅烷基)-5-甲基噻吩
  参考文献：
  名称：

  取代的2-噻吩基三甲基硅烷的碱解速率。从头开始计算单取代噻吩的酸度

  摘要：

  Rates of cleavage in NaOMe-MeOH at 50°C have been determined for the mono-substituted 2-trimethylsilylthiophens X·C4H2S·SiMe3-2 with X = H, 3-NO2, 3-Br, 4-Br-, and 5-NO2, -CN, -COPh, -Me, -OMe and -NMe2, and for one disubstituted compound, 4,5-Br2-C4HS-SiMe3-2. For several compounds the rate and product isotope effects have also been determined. The energies involved in the process X·C4H3S → X·C4H2S−

  DOI：

  10.1016/s0022-328x(00)84581-7

文献信息

• Palladium-catalysed direct arylation of thiophenes tolerant to silyl groups
  作者：Lu Chen、Julien Roger、Christian Bruneau、Pierre H. Dixneuf、Henri Doucet

  DOI：10.1039/c0cc04302h

  日期：——

  The palladium catalysed 5-arylation of 2-(trimethylsilyl)thiophene with aryl bromides via C–H bond functionalisation allows the synthesis of arylated silylthiophenes in only one step.

  钯催化的2-(三甲基硅基)噻吩与芳基溴化物的C-H键官能化的5-芳基化反应允许仅通过一步合成芳基化硅基噻吩。
• Conjugated Bis(triarylboranes) with Disconnected Conjugation
  作者：Nicolas Alexander Riensch、Lukas Swoboda、Artur Lik、Ivo Krummenacher、Holger Braunschweig、Holger Helten

  DOI：10.1002/zaac.202000476

  日期：2021.3.11

  A series of methylene‐bridged bis(triarylboranes) has been synthesized via two complementary routes using metal‐free catalytic Si/B exchange condensation under mild conditions. The title compounds comprise two borane moieties that show effective internal π‐conjugation involving the respective boron centers and the adjacent hetaryl groups. Conjugation between both borane units, however, is disrupted

  在温和的条件下，使用无金属的催化Si / B交换缩合反应，通过两条互补的途径合成了一系列亚甲基桥联的双（三芳基硼烷）。标题化合物包含两个硼烷部分，它们显示出有效的内部π共轭，涉及相应的硼中心和相邻的杂芳基。然而，两个硼烷单元之间的共轭被脂族连接基破坏。循环伏安法揭示出硼中心之间的电子通讯最少，这是由两个紧密间隔的还原过程所证明的。与相关的单硼烷相比，UV-vis光谱显示出红移的吸收带，这归因于亚甲基桥。在末端噻吩环上引入甲基或SiMe 3基团后，会产生进一步的红移。
• New fluorescent bis-dithienylethene (DTE)-based bipyridines as reverse interrupters: single vs. double photochromism
  作者：Lucie Ordronneau、Julien Boixel、Vincent Aubert、Matias S. Vidal、Sergio Moya、Pedro Aguirre、Loic Toupet、J. A. Gareth Williams、Hubert Le Bozec、Véronique Guerchais

  DOI：10.1039/c3ob42119h

  日期：——

  The synthesis and characterization of a series of fluorescent bis-dithienylethene (DTE)-based bipyridines, where the donor (D) and acceptor (A) groups are located on the same thiophene ring of the DTE unit, and their zinc(II) and rhenium(I) complexes are reported. Their photochromic properties have been investigated by UV-visible and 1H NMR spectroscopy. These studies reveal that in non-polar solvents

  一系列基于荧光双二噻吩乙烯（DTE）的联吡啶的合成与表征，其中供体（D）和受体（A）位于DTE单元的同一噻吩环上，并且它们的锌（II）和reported （I）配合物的报道。通过紫外可见和1 H NMR光谱研究了它们的光致变色性质。这些研究表明，在非极性溶剂，可以调节光反应，单VS。通过改变供体基团的性质实现双环封闭。还讨论了溶剂效应以及有机金属部分对这些分子的光致变色行为的影响。最后，在光转化为光平稳状态（PSS）时，由于闭环时的缀合破坏，联吡啶配体观察到荧光猝灭。
• Catalytic and highly enantioselective Friedel–Crafts type reactions of heteroaromatic compounds with trifluoropyruvate and glyoxylate by a dicationic palladium complex
  作者：Kohsuke Aikawa、Yuya Asai、Yūta Hioki、Koichi Mikami

  DOI：10.1016/j.tetasy.2014.06.013

  日期：2014.8

  The highly enantioselective Friedel-Crafts alkylation of furan and thiophene derivatives with trifluoropyruvate, which have never provided the high level of asymmetric induction and yield until now, was achieved by using dicationic palladium complexes as Lewis acid catalysts. Moreover, glyoxylate instead of trifluoropyruvate as an electrophile led to complete change of regioselectivity with 2-trimethylsilylated furan, thiophene, and pyrrole derivatives to give the corresponding heteroarylated products in high yields and enantioselectivities. The respective products with trifluoropyruvate and glyoxylate could also be obtained via sequential catalytic reaction; intramolecular cyclization of alkynyldiols using cationic Au catalyst followed by Friedel-Crafts type reactions using dicationic Pd catalyst. (C) 2014 Elsevier Ltd. All rights reserved.
• Facile Arylation of Four-Coordinate Boron Halides by Borenium Cation Mediated Boro-desilylation and -destannylation
  作者：Daniel L. Crossley、Jessica Cid、Liam D. Curless、Michael L. Turner、Michael J. Ingleson

  DOI：10.1021/acs.organomet.5b00857

  日期：2015.12.28

  The addition of AlCl3 to four-coordinate boranes of the general formula (C-N-chelate)BCl2 results in halide abstraction and formation of three-coordinate borenium cations of the general formula [(C-N-chelate)BCl](+) The latter react with both arylstannanes and arylsilanes by boro-destannylation and -desilylation, respectively, to form arylated boranes. Catalytic quantities of AlCl3 were sufficient to effect high-yielding arylation of (C-N-chelate)BCl2. Boro-destannylation is more rapid than boro-desilylation and leads to double arylation at the boron center, whereas in reactions with arylsilanes either single or double arylation occurs dependent on the nudeophilicity of the arylsilane and on the electrophilicity of the borenium cation. The electrophilicity of the borenium cation derived from 2-phenylpyridine was greater than that of the benzothiadiazole analogues, enabling the boro-desilyation of less nucleophilic silanes and the direct electrophilic borylation of 2-methylthiophene.