di-phenylethynyl-divinylsilane | 197172-17-1

• 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: di-phenylethynyl-divinylsilane
• 英文别名: bis(ethenyl)-bis(2-phenylethynyl)silane
• CAS: 197172-17-1
• 化学式: C₂₀H₁₆Si
• 分子量: 284.433
• InChiKey: XLZYRBLGKBEYQE-UHFFFAOYSA-N

物化性质

• 沸点：
  383.9±15.0 °C(Predicted)
• 密度：
  1.03±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.07
• 重原子数：
  21.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为反应物：
  描述：

  di-phenylethynyl-divinylsilane 在 偶氮二异丁腈 、 LiC₁₀H₈ 、 三正丁基氢锡 、 sodium iodide 作用下， 以 丁酮 、 苯 为溶剂， 反应 41.25h， 生成 3,4-Diphenyl-2,5-bis-trimethylsilanyl-1,1-divinyl-1H-silole
  参考文献：
  名称：

  A bridged spiro[6.6]silatridecane via double 7-endo radical cyclisation

  摘要：

  The double intramolecular radical induced reaction of 5 gives in a highly regioselective reaction via a 7-endo mode the tricyclic silaalkane 7 in 42% yield. In addition. The bicyclic trisilane 8 also formed by a 7-endo cyclisation, is obtained in 33% yield. The structure of 7 has been confirmed by X-ray structure analysis. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00620-6
• 作为产物：
  描述：

  二乙烯基二氯硅烷 、 lithium phenylacetylide 以 正己烷 为溶剂， 生成 di-phenylethynyl-divinylsilane
  参考文献：
  名称：

  Alkynylsilanes and Alkynyl(vinyl)silanes. Synthesis,Molecular Structures and Multinuclear Magnetic Resonance Study

  摘要：

  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。

  DOI：

  10.1515/znb-2010-0609

文献信息

• Combination of 1,2‐Hydroboration and 1,1‐Organoboration: A Convenient Route to 5‐Silaspiro[4,4]nona‐1,6‐diene Derivatives
  作者：Ezzat Khan、Bernd Wrackmeyer、Rhett Kempe

  DOI：10.1002/ejic.200800790

  日期：2008.12

  reactions with 9-borabicyclo[3.3.1]nonane (9-BBN) were studied. 1,2-Hydroboration takes place selectively at the vinyl group, followed by intramolecular 1,1-organoboration to form a 1-silacyclopent-2-ene ring. Repetition of this sequence affords, in essentially quantitative yield, 5-silaspiro[4,4]nona-1,6-diene derivatives bearing substituents in the 1,6-positions and 9-borabicyclo[3.3.1]nonyl groups

  制备了二炔-1-基（二乙烯基）硅烷，并研究了它们与 9-硼双环 [3.3.1] 壬烷 (9-BBN) 的反应。1,2-硼氢化选择性地发生在乙烯基上，然后分子内 1,1-有机硼化形成 1-硅杂环戊-2-烯环。该序列的重复以基本上定量的产率提供在 1,6-位带有取代基和在 2 位带有 9-硼双环 [3.3.1]壬基的 5-硅螺[4,4]壬基-1,6-二烯衍生物。 ,7 位。用过量的乙酸进行原脱硼反应得到仅在 1,6-位带有取代基的相应螺硅烷。所有新化合物均通过溶液中的 NMR 光谱（1H、11B、13C、29Si NMR）进行表征，螺硅烷的两个实例通过固态 X 射线结构分析进行表征。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim,
• Siloles Bearing Si-Vinyl and Si-Allyl Functions. 1,1-Organoboration and Protodeborylation
  作者：Ezzat Khan、Bernd Wrackmeyer

  DOI：10.1515/znb-2009-1002

  日期：2009.10.1

  1,1-Organoboration of dialkyn-1-yl(divinyl)silanes, dialkyn-1-yl(organo)(vinyl)silanes and dialkyn- 1-yl(allyl)(methyl)silane using triethylborane, BEt3, or 9-ethyl-9-borabicyclo[3.3.1]nonane, Et-9- BBN, afforded selectively silole derivatives with Si-vinyl and Si-allyl functions, respectively, bearing the dialkylboryl group in 3-position. The siloles are formed via intermolecular 1,1-alkylboration, followed by intramolecular 1,1-vinylboration. In the cases of several 3-diethylboryl-substituted siloles, smooth and essentially quantitative protodeborylation could be achieved by the reaction of the siloles with an excess of acetic acid at ambient temperature. All new siloles were characterized in solution by multinuclear magnetic resonance spectroscopy (¹H, ¹³C, ¹¹B and ²⁹Si NMR).

  使用三乙基硼、BEt3或9-乙基-9-硼杂双环[3.3.1]非烷、Et-9-BBN对二炔基-1-基(二烯基)硅烷、二炔基-1-基(有机)(乙烯基)硅烷和二炔基-1-基(丙烯基)(甲基)硅烷进行有机硼化反应，选择性地得到带有3-位双烯基和烯丙基官能团的硅杂环化合物，分别带有二烷基硼基团。硅杂环化合物通过分子间的1,1-烷基硼化反应和随后的分子内1,1-乙烯基硼化反应形成。在几种3-二乙基硼基取代的硅杂环化合物中，通过将硅杂环化合物与过量的乙酸在常温下反应，可以实现平滑且基本定量的脱硼反应。所有新合成的硅杂环化合物均通过多核磁共振光谱（¹H，¹³C，¹¹B和²⁹Si NMR）在溶液中进行了表征。
• Synthesis of some di- and tricyclic silaalkanes
  作者：Zhu Teng、Christoph Boss、Reinhart Keese

  DOI：10.1016/s0040-4020(97)00841-7

  日期：1997.9

  The mono-, di- and spirocyclic silaalkanes 5, 6 and 9/10 are readily prepared from the di- and tetraallylsilanes 4 and 8 respectively by Cp2Zr induced ring forming reactions. The diallylsilole 16 reacts at 0 degrees C and in presence of an excess of Cp2Zr to the tricyclic compound 19 whereas the silaspiro[4.4]nonadienes 21 and 22 are formed at room temperature. High stereoselectivity is observed in all of these Cp2Zr induced cyclization reactions. (C) 1997 Elsevier Science Ltd.
• 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。
• A bridged spiro[6.6]silatridecane via double 7-endo radical cyclisation
  作者：Zhu Teng、Reinhart Keese、Helen Stoeckli-Evans

  DOI：10.1016/s0040-4020(98)00620-6

  日期：1998.9

  The double intramolecular radical induced reaction of 5 gives in a highly regioselective reaction via a 7-endo mode the tricyclic silaalkane 7 in 42% yield. In addition. The bicyclic trisilane 8 also formed by a 7-endo cyclisation, is obtained in 33% yield. The structure of 7 has been confirmed by X-ray structure analysis. (C) 1998 Elsevier Science Ltd. All rights reserved.