氯(二甲基)2-噻吩基硅烷 | 18139-63-4

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 中文名称: 氯(二甲基)2-噻吩基硅烷
• 英文名称: chlorodimethyl-2-thienylsilane
• 英文别名: 2-thienyldimethylchlorosilane；chlorodimethyl(thiophen-2-yl)silane；me2(2-th)SiCl；Chlor-dimethyl-[2]thienyl-silan；chloro-dimethyl-thiophen-2-ylsilane
• CAS: 18139-63-4
• 化学式: C₆H₉ClSSi
• mdl: MFCD09039081
• 分子量: 176.742
• InChiKey: DEPVFYAOAUKMFL-UHFFFAOYSA-N

物化性质

• 沸点：
  199.0±13.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.93
• 重原子数：
  9
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 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：

  氯(二甲基)2-噻吩基硅烷 在 copper(l) iodide 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 0.08h， 以71%的产率得到2,2'-联二噻吩
  参考文献：
  名称：

  Copper(I)-catalysed homocoupling of organosilicon compounds: synthesis of biaryls, dienes and diynes

  摘要：

  碘化亚铜在温和条件下催化芳基、烯基和炔基取代的氯代或氟代二甲基硅烷的自偶联反应，分别生成联芳基、二烯和二炔化合物。

  DOI：

  10.1039/a608384f
• 作为产物：
  描述：

  dimethyl-thiophen-2-yl-silane 在 磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以90%的产率得到氯(二甲基)2-噻吩基硅烷
  参考文献：
  名称：

  Gotteland; Junquero; Oms, Medicinal Chemistry Research, 1996, vol. 6, # 5, p. 333 - 342

  摘要：

  DOI：

文献信息

• Facile Construction of Spirocyclopropanated Bi-, Tri- and Tetracyclic Skeletons by Novel Cascades Involving Intra- and Intermolecular Heck Reactions of 2-Bromo-1,6-enynes and Bicyclopropylidene
  作者：Michael Schelper、Armin de Meijere

  DOI：10.1002/ejoc.200400668

  日期：2005.2

  elevated temperatures (120−140 °C) the initially formed tetraenes underwent 6π-electrocyclization to give spiro[cyclopropane-1,4′-bicylo[4.3.0]-1(6),2-dienes] 21-R, 22-R and 23-R. This novel class of spirocyclopropanated oligocycles is also accessible by a one-pot protocol. The highest yields for both the tetraenes and bicyclo[4.3.0]nonadiene and its heteroanalogues were obtained with bulky substituents

  在炔烃末端具有庞大取代基的无环 2-溴-1,6-烯炔 5-R、9-R 和 11-R 在 80°C 的钯催化下与高度紧张的双环亚丙基 (12) 共环化，得到交叉共轭四烯 13-R、18-R 和 19-R 的产率中等至良好 (34-71%)。只有 5-Ph 的共环化产生了额外的产物，它被确定为 11 元环 20。在升高的温度（120-140°C）下，最初形成的四烯经历 6π-电环化得到螺[环丙烷-1,4'-双环[4.3.0]-1(6),2-二烯] 21-R、22-R 和 23-R。这种新型的螺环丙烷化低聚环也可通过一锅法获得。四烯和双环的产率最高[4.3。0]壬二烯及其杂类似物在前体的炔末端具有大的取代基。含杂原子的前体 9-R 和 11-R 的产率低于其全碳类似物 5-R。无环 2-bromo-1,8-dien-6-ynes 28a,b,c 在钯催化下与双环亚丙基 (12) 在 110 °C
• Preparation and Reaction Chemistry of Novel Silicon-Substituted 1,3-Dienes
  作者：Partha Choudhury、Mark Welker

  DOI：10.3390/molecules200916892

  日期：——

  containing non transferrable groups known to promote transmetallation were prepared by Grignard chemistry and enyne metathesis. These dienes participated in one pot metathesis/Diels-Alder reactions in regio- and diastereoselective fashions. Electron-rich alkenes showed the fastest rates in metathesis reactions, and ethylene, a commonly used metathesis promoter slowed enyne metathesis. 2-Pyridyldimethylsilyl

  通过格氏化学和烯炔复分解制备了含有已知可促进金属转移作用的不可转移基团的2-硅取代的1,3-二烯。这些二烯以区域选择性和非对映选择性方式参与了一个锅置换/ Diels-Alder反应。富电子烯烃在复分解反应中显示出最快的速率，而乙烯（一种常用的复分解促进剂）减慢了烯炔的复分解。2-吡啶基二甲基甲硅烷基和2-噻吩基二甲基甲硅烷基取代的Diels-Alder环加合物参与了交叉偶联化学反应，并且2-噻吩基二甲基甲硅烷基取代的环加合物在非常温和的反应条件下进行了交叉偶联。
• Synthesis of novel conjugated oligomers for second-order nonlinear optics: incorporation of a central spacer as a conjugation modulator
  作者：Jian Xin Zhang、Philippe Dubois、Robert Jérôme

  DOI：10.1039/a606547c

  日期：——

  A new series of second-order nonlinear optical chromophores has been synthesized that consists of a conjugated segment end-capped with an electron acceptor and an electron donor, respectively, and a central spacer intended to modulate the electro-optical effect. Conjugated chains have been tailored with trans-vinylene-1,5-thienylene as the building unit and N,N-dimethylamino and nitro groups as the donor–acceptor pair. Four spacers have been incorporated into the central part of the conjugated oligomers, which range from saturated to totally unsaturated functions, i.e. from methylene to vinylene units. The general strategy relies upon two consecutive Wittig or Wittig–Horner reactions between the spacer precursor and an aromatic phosphonium or phosphonate bearing the strong electron donor and the acceptor, respectively. Two synthetic pathways have been studied. The first procedure is based on the use of a symmetric precursor for the spacer. However, a reaction byproduct is formed, which must be removed and decreases the reaction efficiency. The second approach requires an asymmetric precursor for the spacer, the synthesis of which is a multistep process. In order to evaluate the effect of the spacer, a completely conjugated oligomer has been prepared by the one-step coupling of two conjugated segments end-functionalized by the electron donor and the acceptor, respectively.

  一种新的二阶非线性光学染料系列已被合成，该系列由一个共轭段组成，两端分别封端为电子受体和电子给体，并包含一个中心间隔器，旨在调节电光效应。共轭链使用反式乙烯-1,5-噻吩单元作为构建单元，N,N-二甲基氨基和硝基作为给体–受体对。四种间隔器被引入到共轭 oligomer 的中央部分，这些间隔器从饱和功能到完全不饱和功能，即从亚甲基到乙烯基单元。一般策略依赖于间隔器前体与带有强电子给体和受体的芳香族膦盐或膦酸酯之间的两次连续 Wittig 或 Wittig–Horner 反应。研究了两条合成路径。第一种程序基于使用对称前体作为间隔器。然而，会形成一个反应副产物，必须去除，这降低了反应效率。第二种方法需要不对称的间隔器前体，其合成是一个多步过程。为了评估间隔器的影响，通过将两个分别被电子给体和受体功能化的共轭段进行一步耦合，制备了一个完全共轭的 oligomer。
• Electrochemical synthesis of bis(2-thienyl) silanes, 2-thienylchlorosilanes, bis[5-(2-bromothienyl)]silanes, and 5-(2-bromothienyl) dimethylchlorosilane, precursors of poly[(silanylene)thiophene]s
  作者：Carole Moreau、Françoise Serein-Spirau、Michel Bordeau、Claude Biran、Jacques Dunoguès

  DOI：10.1016/0022-328x(96)06333-4

  日期：1996.9

  Bis(2-thienyl)silanes and bis[5-(2-bromothienyl)]silanes were synthesized by electrochemical reduction of monohalothiophenes (Br,Cl) and 2,5-dibromothiophene respectively in the presence of a dichlorosilane in THF or LME, using an undivided cell, a sacrificial Mg or Al anode, a constant current density and tetrabutylammonium bromide as the supporting electrolyte. In addition, when dichlorosilanes were

  通过在THF或LME中在二氯硅烷存在下分别通过单卤代噻吩（Br，Cl）和2,5-二溴噻吩的电化学还原反应，合成了双（2-噻吩基）硅烷和双[5-（2-溴噻吩基）]硅烷一个未分割的电池，一个牺牲性的Mg或Al阳极，一个恒定的电流密度和四丁基溴化铵作为支持电解质。另外，当大量使用二氯硅烷时，卤代噻吩仅进行单偶联反应，选择性地导致噻吩基氯硅烷，这揭示了电化学方法的多功能性。
• Nickel‐Catalyzed Cross‐Electrophile 1,2‐Silyl‐Arylation of 1,3‐Dienes with Chlorosilanes and Aryl Bromides
  作者：Qiu‐Quan Pan、Liangliang Qi、Xiaobo Pang、Xing‐Zhong Shu

  DOI：10.1002/anie.202215703

  日期：2023.1.23

  silylarylation of 1,3-dienes using chlorosilanes and aryl bromides is reported. The reaction affords 1,2-linear-silylated products, a selectivity that is distinct from those obtained with conventional hydro- and carbosilylation methods. This work shows the possibility to achieve the silyl-functionalization of unsaturated bonds using readily available chlorosilanes.

  报道了使用氯硅烷和芳基溴的镍催化的 1,3-二烯还原性甲硅烷基化反应。该反应提供 1,2-线性甲硅烷基化产物，其选择性不同于使用常规氢化和碳硅烷化方法获得的产物。这项工作表明使用现成的氯硅烷实现不饱和键的甲硅烷基官能化的可能性。