phenyltris(phenylethynyl)silane | 18866-47-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: phenyltris(phenylethynyl)silane
• 英文别名: tris(phenylethynyl)phenylsilane；phenyltri(phenylethynyl)silane；phenyl-tris-phenylethynyl-silane；Phenyl-tris-phenylaethinyl-silan；Tri(phenylethinyl)phenylsilan；Phenyl-tri(phenylethynyl)silane；phenyl-tris(2-phenylethynyl)silane
• CAS: 18866-47-2
• 化学式: C₃₀H₂₀Si
• 分子量: 408.574
• InChiKey: SSGJCHOXRPPNSK-UHFFFAOYSA-N

物化性质

• 熔点：
  148 °C
• 沸点：
  535.5±33.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.12
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• 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

反应信息

• 作为反应物：
  描述：

  phenyltris(phenylethynyl)silane 以 四氢呋喃 、 氘代苯 为溶剂， 反应 24.0h， 生成 C₄₆H₅₀B₂Si
  参考文献：
  名称：

  Si取代的1-硅杂环丁烯衍生物的合成和核磁共振光谱表征

  摘要：

  三炔-1-基(有机)硅烷与一当量和两当量的9-硼双环[3.3.1]壬烷、9-BBN的硼氢化反应分别得到二炔-1-基硅烷和炔-1-基硅烷。炔-1-基硅烷衍生物在室温下是稳定的，可以在干燥的氩气下长期储存。这些化合物是用于进一步重排以提供具有 Si-烯基或 Si-炔基官能团的新型 1-硅杂环丁烯衍生物的有吸引力的材料。硼氢化反应由 Si-R1 功能很好地控制，即具有 R1 = Ph 的起始硅烷选择性地提供一个 Si-C≡C 键与一当量的 9-BBN 的硼氢化，而其他两个官能团保持不变。在温和的反应条件 (25°C) 下，R1 = Me 的起始硅烷生成含有二炔-1-基硅烷的混合物，炔-1-基硅烷和它们各自的1-硅杂环丁烯衍生物。所有新化合物都对空气和水分敏感，并通过多核磁共振波谱（1H、13C、11B、29Si NMR）在溶液中进行了研究。

  DOI：

  10.2478/s11532-010-0122-z
• 作为产物：
  描述：

  Sodium;8-phenyl-8,8'-spirobi[7,9-dioxa-8-silanuidabicyclo[4.3.0]nona-1,3,5-triene] 、 苯基乙炔基溴化镁 生成 phenyltris(phenylethynyl)silane
  参考文献：
  名称：

  BOUDIN A.; CERVEAU G.; CHUIT C.; CORRIU J. P.; REYE C., ANGEW. CHEM., 98,(1986) N 5, 472-473

  摘要：

  DOI：

文献信息

• Alkynylsilanes and Alkynyl(vinyl)silanes. Synthesis,Molecular Structures and Multinuclear Magnetic Resonance Study
  作者：Bernd Wrackmeyer、Stefan Bayer、Oleg L. Tok、Elena V. Klimkina、Wolfgang Milius、Rhett Kempe、Ezzat Khan

  DOI：10.1515/znb-2010-0609

  日期：2010.6.1

  Alkynylsilanes bearing one to four alkynyl groups at silicon, with organyl groups (Me, Ph, Vin), H, Cl at silicon, and with substituents H, ⁿBu, ^tBu, Ph, C₆H₄-4-Me, 3-thienyl, CH₂NMe₂ at the C≡C bond, were prepared, and their ¹³C and ²⁹Si NMR data are reported. The results of X-ray structure analyses of three representative derivatives [di(phenylethynyl)dimethylsilane, di(phenylethynyl) methyl(phenyl)silane, and tri(phenylethynyl)methylsilane] are presented. The chemistry of mono- and dialkynylsilanes was further developed to prepare compounds with alternating Si atoms and C≡C bonds, affording new dialkynylsilanes as well as numerous new vinylsilanes which have also been characterized by ¹³C and ²⁹Si NMR spectroscopy in solution. In the case of ethynyl(triphenylsilylethynyl) dimethylsilane, the molecular structure was determined by X-ray diffraction.

  带有硅原子上一个到四个炔基的炔基硅烷，以及硅原子上带有甲基、苯基、乙烯基、氢、氯的有机基团，以及炔键上带有H、正丁基、叔丁基、苯基、4-甲基苯基、3-噻吩基、CH2NMe2等取代基的炔基硅烷已经制备，并报告了它们的13C和29Si核磁共振数据。三个代表性衍生物[二(苯乙炔基)二甲基硅烷、二(苯乙炔基)甲基(苯基)硅烷和三(苯乙炔基)甲基硅烷]的X射线结构分析结果被呈现。单炔基硅烷和二炔基硅烷的化学性质进一步发展，以制备交替的硅原子和C≡C键的化合物，得到了新的二炔基硅烷以及许多新的乙烯基硅烷，这些化合物也通过溶液中的13C和29Si核磁共振光谱进行了表征。在乙炔基(三苯基硅炔基)二甲基硅烷的情况下，分子结构是通过X射线衍射确定的。
• Dehydrogenative Silylation of Terminal Alkynes with Hydrosilanes under Zinc-Pyridine Catalysis
  作者：Teruhisa Tsuchimoto、Masakazu Fujii、Yoshihiko Iketani、Masaru Sekine

  DOI：10.1002/adsc.201200310

  日期：2012.11.12

  A combination of zinc triflate and pyridine in a nitrile medium was found to act as an effective catalytic system for dehydrogenative silylation with flexible pieces of terminal alkynes and hydrosilanes, thereby producing diverse alkynylsilanes in high to excellent yields.

  发现三氟甲磺酸锌和吡啶在腈介质中的组合可作为有效的催化体系，用于与末端炔烃和氢硅烷的柔性片段进行脱氢甲硅烷基化，从而以高到极好的收率生产各种炔基硅烷。
• Dehydrogenative Coupling between Hydrosilanes and Alkynes Catalyzed by Alkoxides, Alkylmetals, and Metalamides
  作者：Jun-ichi Ishikawa、Masayoshi Itoh

  DOI：10.1006/jcat.1999.2530

  日期：1999.7

  selective dehydrogenative coupling reaction between phenylsilane and ethynylbenzene occurred in the presence of some homogeneous base catalysts such as alkoxides, alkyl compounds, and the amides of alkali metals or barium. The order of the catalytic activities was Ba(OR)2>LiN(SiMe3)2∼n-BuLi>LiOEt. Barium alkoxide showed the highest activity and selectivity for the reaction, and gave the polymer poly[(p

  苯硅烷和乙炔基苯之间的选择性脱氢偶联反应是在某些均相碱催化剂（例如醇盐，烷基化合物以及碱金属或钡的酰胺）的存在下发生的。催化活性的次序是钡（OR）2 >的LiN（森达3）2〜Ñ正丁基锂> LiOEt。钡醇盐显示出对反应最高的活性和选择性，并给出了聚合物的聚苯基硅烷中的与反应[（phenylsilylene）亚乙炔基-1,3-苯撑乙炔]米-diethynylbenzene。讨论了催化活性与催化剂碱度之间的关系，并提出了同时涉及金属乙炔化物和金属氢化物的反应机理。
• Hydroalumination and Hydrogallation Reactions with Tri(ethynyl)silanes - Generation of Compounds with up to Three Coordinatively Unsaturated Aluminium Atoms
  作者：Werner Uhl、Jörg Bohnemann、Denis Heller、Alexander Hepp、Marcus Layh

  DOI：10.1002/zaac.201100418

  日期：2012.1

  h]2 (4a, E = Al, 4b, E = Ga) and (Me)Si[(tBu2Al)C=C(H)Ar]3 (5, Ar = Ph; 6, Ar = C6H4Me). Compounds 2–4 show a relatively close interaction between the coordinatively unsaturated aluminium or gallium atoms and one of the Cα(≡C) atoms of unreacted alkyne substituents [245 (E = Al) and 266 pm (E = Ga)] that stabilises the kinetically favoured cis addition products with E and hydrogen on the same side

  三（乙炔基）硅烷的氢铝化或水镓化，RSi(C≡C-Ar)3（1a，R = Ph，Ar = Ph；1b，R = Me，Ar = Ph；1c，R = Me，Ar = C6H4Me） , 与元素氢化物 H-EtBu2 (E = Al, Ga) 在环境温度下以 1:1 到 1:3 的化学计量比产生加成产物 (PhC≡C)2(R)Si[(tBu2E)C=C (H)Ph] (2, R = Ph, E = Ga; 3a, R = Me, E = Al; 3b, R = Me, E = Ga), (PhC≡C)(Me)Si[(tBu2E) C=C(H)Ph]2 (4a, E = Al, 4b, E = Ga) 和 (Me)Si[(tBu2Al)C=C(H)Ar]3 (5, Ar = Ph; 6, Ar = C6H4Me）。化合物 2-4 显示出配位不饱和铝或镓原子与未反应炔烃取代基的 Cα(≡C) 原子之一
• Synthesis, characterization, and non-isothermal curing kinetics of two silicon-containing arylacetylenic monomers
  作者：Dexin Tan、Tiejun Shi、Zhong Li

  DOI：10.1007/s11164-011-0291-1

  日期：2011.10

  Vinyltri(phenylethynyl)silane ((ph–C≡C)3–Si–C=CH2; VTPES) and phenyltri(phenylethynyl)silane ((ph–C≡C)3–Si–ph; PTPES) were synthesized by Grignard reaction. Their molecular structures were characterized by means of 1H NMR, 13C NMR, 29Si NMR, and FT-IR spectroscopy. Their nonisothermal thermal curing processes were characterized by DSC, and the corresponding kinetic data, for example activation energy (E), pre-exponential factor (A), and the order of the reaction (n), were obtained by the Kissinger method. The results showed that the melting points of VTPES and PTPES were 84 and 116 °C, respectively. Their curing reaction rates were consistent with first-order kinetic equations. VTPES monomer had a lower activation energy and curing temperature as a result of coordination between reactive groups.

  通过格氏反应合成乙烯基三(苯基乙炔基)硅烷((ph–C≡C)3–Si–C=CH2; VTPES)和苯基三(苯基乙炔基)硅烷((ph–C≡C)3–Si–ph; PTPES) 。通过1H NMR、13C NMR、29Si NMR和FT-IR光谱对其分子结构进行了表征。采用DSC对其非等温热固化过程进行了表征，并通过Kissinger方法获得了相应的动力学数据，例如活化能（E）、指前因子（A）和反应级数（n）。结果表明，VTPES 和 PTPES 的熔点分别为 84 和 116 °C。它们的固化反应速率符合一级动力学方程。由于反应基团之间的配位，VTPES单体具有较低的活化能和固化温度。