三乙烯基氯硅烷 | 1871-21-2

• 物质功能分类: 化学试剂 - 硅烷试剂
• 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: 三乙烯基氯硅烷
• 中文别名: 二甘醇单(2-乙己基)
• 英文名称: chlorotrivinylsilane
• 英文别名: trivinylchlorosilane；trivinylsilyl chloride；chloro-tris(ethenyl)silane
• CAS: 1871-21-2
• 化学式: C₆H₉ClSi
• mdl: MFCD00236523
• 分子量: 144.676
• InChiKey: NNKJLYMBVRDUEI-UHFFFAOYSA-N

物化性质

• 熔点：
  <0°C
• 沸点：
  128 °C
• 密度：
  0.934
• 闪点：
  15°C

计算性质

• 辛醇/水分配系数(LogP)：
  3.53
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

安全信息

• TSCA：
  No
• 安全说明：
  S16,S3/7,S36/37/39,S45,S9
• 危险类别码：
  R34,R11
• 危险品运输编号：
  UN 2985
• 海关编码：
  2931900090
• 储存条件：
  储存温度应保持在2-8°C，需密封并确保环境干燥。

反应信息

• 作为反应物：
  描述：

  三乙烯基氯硅烷 在 bis(tetrabutylammonium) hexachloroplatinate(IV) 、 叔丁基锂 作用下， 以 四氢呋喃 、 乙醚 、 正戊烷 为溶剂， 反应 83.17h， 生成 (tris[2-(dimethylphenylsilyl)ethyl])([4-(dimethylaminomethyl)-2-(trimethylsilylthio)phenyl])silane
  参考文献：
  名称：

  A recyclable nanosize aminoarenethiolato copper(I) catalyst for C–C coupling reactions

  摘要：

  An aminoarenethiolato copper(I) catalyst was attached to a carbosilane dendritic wedge, which had been prepared via a novel convergent synthetic method. Compared with the unsupported complex, this novel dendritic copper(I) catalyst is more robust towards hydrolysis and oxidation and has increased solubility in common organic solvents. The catalytic activity of the dendritic, copper catalyst was tested in the 1,4-addition of Et2Zn to 2-cyclohexenone. In both polar (Et2O) and apolar (hexane) solvents excellent activity was observed. The fact that the catalytic copper site remains attached to the nanosize dendritic aminoarenethiolate ligand allows separation of this catalyst by means of nanofiltration. (C) 2004 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2004.07.023
• 作为产物：
  描述：

  trivinylsilane 在 三氯异氰尿酸 作用下， 以 二氯甲烷 为溶剂， 以98.7%的产率得到三乙烯基氯硅烷
  参考文献：
  名称：

  Utility of trichloroisocyanuric acid in the efficient chlorination of silicon hydrides

  摘要：

  The potential of trichloroisocyanuric acid (TCCA) as a chlorination agent for efficient conversion of Si-H functional silanes and siloxanes to the corresponding Si-Cl functional moieties was explored. In comparison to methods using other chlorinating agents, TCCA is inexpensive, results in a much faster reaction and produces a high purity product with a conversion that is essentially quantitative. A variety of chloro derivatives of linear and cyclic structures have been synthesized from silicon hydrides using this reagent with impressive yields that typically exceed 90%: PhSiCl3 (97.5%); PhMeSiCl2 (95.5%); Ph3SiCl (97.5%); Vi(3)SiCl (98.7%); (EtO)(3)SiCl (99.7%); t-Bu3SiCl (similar to 100%); (MeClSiO)(4) (86.5%); (MeClSiO)(5) (95%); (MeClSiO)(7) (96.5%); Ph(OEt)(2)SiCl (98%); ClMe2SiOSiMe2Cl (98.6%); ClMe2SiOSiMeClOSiMe2Cl (94.6%); ClMe2Si(OSiMeCl)(2)OSiMe2C l (92.3%); (Me3SiO)(3)SiCl (97%); Me3SiOSiClPhOSiMe3 (99%); Me3SiO(SiMeClO)(3)SiMe3 (95.7%); ClSi(OSiMe3)(2)OSi(OSiMe3) Cl-2 (93.6%).For monohydridosilanes, dichloromethane (CH2Cl2) was a suitable solvent in which nearly quantitative conversion was observed within several minutes following the addition of the silanes to TCCA. For certain cyclic and linear siloxanes, and especially silanes containing multiple hydrogen atoms on the same silicon for which the reaction is sluggish in CH2Cl2, tetrahydrofuran (THF) was the preferred solvent. For a sterically demanding silane that did not undergo chlorination even in THF viz., HSi(OSiMe3)(2)O-Si(OSiMe3)(2)H, 1,2-dichloroethane was the best solvent. (c) 2007 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2006.12.032
• 作为试剂：
  描述：

  二氧化碳 、 三乙烯基氯硅烷 、 二甲胺 在 氮气 、 二氧化碳 、 二甲胺 、 三乙烯基氯硅烷 、 正己烷 作用下， 以 正己烷 为溶剂， 22.0 ℃ 、7.11 kPa 条件下， 以to yield the desired product, 74 g, yield 68%的产率得到(Dimethylamino)trivinylsilane
  参考文献：
  名称：

  Novel stationary phases for use in high-performance liquid chromatography

  摘要：

  本发明提供了新型色谱材料和色谱柱。本发明提供了一种单官能团硅烷化合物化学键合到基底上，该单官能团硅烷化合物具有两个基团R和R'，该单官能团硅烷化合物的形式为：其中R基团独立地选自烯基、炔基和苯基组成的群体，R'选自烷基、取代烷基、烯基、取代烯基、芳基、取代芳基、烷基胺、酰胺、醚、醇、氨基甲酸酯、酯、阴离子交换剂和阳离子交换剂组成的群体。本发明还提供了制造和设计柱的方法。

  公开号：

  US20050242038A1

文献信息

• 一种合成硅基磷簇合物的方法及其产品
  申请人：杭州师范大学

  公开号：CN111606950A

  公开（公告）日：2020-09-01

  本发明公开了一种合成硅基磷簇合物的方法，包括步骤：(1)惰性气体保护下，向反应器内加入极性溶剂、金属还原剂M、红磷和催化剂，搅拌加热反应；(2)将步骤(1)所得反应体系冷却并维持在‑20℃以下，加入卤代硅烷，然后自然升温至室温并继续反应，反应完毕后经后处理得到如下式(I)所示产物；其中，Silyl代表通式R1R2R3Si，R1、R2、R3基团分别独立选自饱和烷烃基、不饱和烃基、烷氧基或芳基。本发明还公开了所述方法合成的硅基磷簇合物。
• Novel Silicon-Based Patchouli Odorants of the Trialkyl(1-hydroxy-1-methylethyl)silane Type: Design, Synthesis, and Olfactory Properties
  作者：Astrid Sunderkötter、Sabine Lorenzen、Reinhold Tacke、Philip Kraft

  DOI：10.1002/chem.201000549

  日期：2010.7.5

  synthesized and studied for their olfactory properties. All of the silanes studied exhibit at least one of the main patchouli odor descriptors ‘woody,’ ‘earthy,’ and ‘camphoraceous,’ and some even exhibit all of them. The silanes MeR2SiC(OH)Me2 (12) and R3SiC(OH)Me2 (14) (R=cyclopropyl) were found to resemble natural patchouli oil most closely, with an even lower odor threshold than the natural lead

  叔丁基（1-羟基-1-甲基乙基）二甲基硅烷（5），一硅杂取代的开环衍生物的最近报道广藿香引线结构（4A - [R *，8α - [R *） - 1,1,8a-trimethyldecahydronaphthalene甲基-4a-醇（4），和一些相关的三烷基（1-羟基-1-甲基乙基）硅烷和进一步的衍生物，化合物8 - 24，用不同的硅结合的取代基（ME等，我PR，ç PR，吨卜，i Bu，c Pent，乙烯基，SiMe 3）合成并研究其嗅觉特性。所研究的所有硅烷均表现出至少一种主要的广香气味描述符“木质”，“土”和“樟脑”，甚至有些甚至全部表现出来。发现硅烷MeR 2 SiC（OH）Me 2（12）和R 3 SiC（OH）Me 2（14）（R =环丙基）最接近天然广patch香油，气味阈值比天然铅更低结构（-）-广atch香酚（1）。为了完成该结构与气味的关系研究，需要使用12和14的碳类似物（Si
• Nickel‐Catalyzed, Reductive C(sp ³ )−Si Cross‐Coupling of α‐Cyano Alkyl Electrophiles and Chlorosilanes
  作者：Liangliang Zhang、Martin Oestreich

  DOI：10.1002/anie.202107492

  日期：2021.8.16

  A nickel/zinc-catalyzed cross-electrophile coupling of alkyl electrophiles activated by an α-cyano group and chlorosilanes is reported. Elemental zinc is the stoichiometric reductant in this reductive coupling process. By this, a C(sp3)−Si bond can be formed starting from two electrophilic reactants whereas previous methods rely on the combination of carbon nucleophiles and silicon electrophiles or

  报道了由 α-氰基和氯硅烷活化的烷基亲电试剂在镍/锌催化下的交叉亲电偶联。元素锌是该还原偶联过程中的化学计量还原剂。由此，可以从两种亲电反应物开始形成C(sp 3 )-Si键，而之前的方法依赖于碳亲核试剂和硅亲电试剂的组合，反之亦然。
• Spherosilicates with peripheral malonic acid and vinyl end groups
  作者：Zhongliang Shen、Jongsik Kim、Jingmei Shen、Christopher M. Downing、Sungsik Lee、Harold H. Kung、Mayfair C. Kung

  DOI：10.1039/c3cc40533h

  日期：——

  Two novel spherosilicates comprised of an octahedral Si8O12 core, [Si8O12]-(OSiMe2CH2CH2CH2CH(COOH)2)8 and [Si8O12]-(OSiMe2CH2CH2CH2CH(COOSi(CHCH2)3)2)8, were synthesized from [Si8O12]-(OSiMe2H)8. These new structures have high densities of peripheral functional groups, and the second structure also possesses silyl ester bonds that are easily cleavable under mild conditions. These functionalities enable these structures to be modified further and to have many potential applications. We demonstrated one by cross-linking the vinyl-terminated spherosilicate to form nanospheres with a narrow size distribution and utilizing the hydrophilic interior to accommodate a Pd salt in a toluene solution.

  合成了两种新型的球硅酸盐，它们由一个八面体的Si8O12核心组成，分别为[Si8O12]-(OSiMe2CH2CH2CH2CH(COOH)2)8和[Si8O12]-(OSiMe2CH2CH2CH2CH(COOSi(CHCH2)3)2)8。这些新结构具有高密度的外围功能基团，第二种结构还具有在温和条件下易于断裂的硅酯键。这些功能使得这些结构能够进一步改性，并具有许多潜在的应用。我们通过交联乙烯基终端的球硅酸盐，形成了具有窄尺寸分布的纳米球，并利用其亲水的内部在甲苯溶液中包容Pd盐，从而展示了一种应用。
• Alpha carbocation stabilization by silicon, germanium and tin
  作者：John A. Soderquist、Alfred Hassner

  DOI：10.1016/s0040-4039(00)82072-9

  日期：1988.1

  The hydrolyses of a number of α-metalloidal vinyl ethers were found to undergo a rate-limiting protonation to produce α- silyl, germyl or stannyl carbocations. Comparative rate data leads to the ordering: C>Sn>Ge>Si>H, for the stabilization of such intermediates.

  发现许多α-准金属乙烯基醚的水解进行限速质子化以产生α-甲硅烷基，癸基或苯乙烯基碳正离子化。比较速率数据导致以下顺序：C> Sn> Ge> Si> H，以稳定此类中间体。