bis(dimethylsilyl)acetylene | 34664-55-6

• 分子结构分类: 有机化合物 - 有机盐 - 有机金属盐
• 英文名称: bis(dimethylsilyl)acetylene
• 英文别名: bis(dimethylsilyl)ethyne；Bis(dimethylsilyl)acetylen；(Ethyne-1,2-diyl)bis(dimethylsilane)；2-dimethylsilylethynyl(dimethyl)silane
• CAS: 34664-55-6
• 化学式: C₆H₁₄Si₂
• 分子量: 142.348
• InChiKey: VMYKPXGBTXNTFD-UHFFFAOYSA-N

物化性质

• 沸点：
  120-122 °C

计算性质

• 辛醇/水分配系数(LogP)：
  1.04
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  bis(dimethylsilyl)acetylene 在 溴 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以63.5%的产率得到Bis(bromodimethylsilyl)acetylene
  参考文献：
  名称：

  1,6-Dihydro-1,6-disilapentalene derivatives by 1,1-organoboration of triynes

  摘要：

  The triynes (RC)-C-1=C-SiMe2-C=C-SiMe2-C=CR1 [R-1 = H (3), SiMe3 (4) SnMe3 (5)] were prepared, and their reactivity towards triorganoboranes R3B 6 [R = Et (a), CH2Ph (b), Ph (c), 2-thienyl (d)] was studied. In the case of 3, decomposition was observed whereas the reaction of 4 and 5 with 6 affords the 1,6-dihydro-1,6-disilapentalene derivatives 7a-d (from 4) and 9a, c (from 5) in almost quantitative yield. This is the result of stereo- and regioselective intermolecular 1,1-organoboration in the first step of the reaction, followed by two consecutive intramolecular 1,1-vinyloborations. The products were characterised by their H-1-,B- 11-, C-13-, Si-29- and Sn-119-NMR data. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(98)00529-4
• 作为产物：
  描述：

  二甲基一氯硅烷 、 乙炔 在 正丁基锂 作用下， 以 正己烷 为溶剂， 反应 12.0h， 以37%的产率得到bis(dimethylsilyl)acetylene
  参考文献：
  名称：

  1,6-Dihydro-1,6-disilapentalene derivatives by 1,1-organoboration of triynes

  摘要：

  The triynes (RC)-C-1=C-SiMe2-C=C-SiMe2-C=CR1 [R-1 = H (3), SiMe3 (4) SnMe3 (5)] were prepared, and their reactivity towards triorganoboranes R3B 6 [R = Et (a), CH2Ph (b), Ph (c), 2-thienyl (d)] was studied. In the case of 3, decomposition was observed whereas the reaction of 4 and 5 with 6 affords the 1,6-dihydro-1,6-disilapentalene derivatives 7a-d (from 4) and 9a, c (from 5) in almost quantitative yield. This is the result of stereo- and regioselective intermolecular 1,1-organoboration in the first step of the reaction, followed by two consecutive intramolecular 1,1-vinyloborations. The products were characterised by their H-1-,B- 11-, C-13-, Si-29- and Sn-119-NMR data. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0022-328x(98)00529-4

文献信息

• Kinetics and mechanisms of .alpha.- and .beta.-eliminations of alkoxysilanes from saturated and unsaturated carbon frameworks
  作者：Sukhamaya. Bain、Sina. Ijadi-Maghsoodi、Thomas J. Barton

  DOI：10.1021/ja00216a039

  日期：1988.4

  favorable elimination of Me/sub 3/SiOMe from Me/sub 3/SiSiMe/sub 2/CH/sub 2/OMe does not occur. From kinetic studies and trapping experiments, this is found to be due to a more favorable A-factor for three-centered elimination of :CH/sub 2/. Three-centered elimination of Me/sub 3/SiOMe from an sp/sup 2/-hybridized carbon to afford a vinylidene is found to be more facile than the analogous elimination from

  尽管 Me/sub 3/SiCH/sub 2/SiMe/sub 2/OMe 经历了 Me/sub 3/SiOMe 的热诱导 ..beta..-消除以提供二甲基硅烯，但 Me/sub 3/SiOMe 从热力学上有利地消除Me/sub 3/SiSiMe/sub 2/CH/sub 2/OMe 不会发生。从动力学研究和捕获实验中，发现这是由于对三中心消除 :CH/sub 2/ 更有利的 A 因子。发现从 sp/sup 2/-杂化碳中三中心消除 Me/sub 3/SiOMe 以提供亚乙烯基比从 sp/sup 3/-杂化碳中的类似消除更容易，因为两者都更有利活化能和 A 因子。因此，由于 ..cap alpha..-消除到 H/sub 2/C= 的更大便利性，不会发生从 H/sub 2/-C(OMe)SiMe/sub 2/SiMe/sub 3/ 形成硅丙二烯C：。
• Stepwise Reactions of Dimethylsilyl Acetylenes with Octacarbonyldicobalt
  作者：Sonae Kotani、Toshihiro Matsumoto、Hidemasa Yamaguchi、Kyo Shiina、Kenkichi Sonogashira

  DOI：10.1246/cl.1989.293

  日期：1989.2

  Treatment of bis(dimethylsilyl)acetylene 1 with more than two molar amount of octacarbonyldicobalt in cyclohexane gave the complex [(CO)4CoSiMe2C≡C–SiMe2Co(CO)4]Co2(CO)6, while treatment of 1 with one or 1.5 molar amount of octacarbonyldicobalt produced the complexes [HSiMe2C≡CSiMe2H]Co2(CO)6 and [HSiMe2C≡CSiMe2Co(CO)4]Co2(CO)6, respectively. The reactions of dimethyl(phenylethynyl)silane and its homologs with Co2(CO)8 were also investigated.

  用超过两摩尔量的八羰基二钴在环己烷中处理双(二甲基硅基)乙炔1，生成了复合物[(CO)4CoSiMe2C≡C–SiMe2Co(CO)4]Co2(CO)6，而用一摩尔或1.5摩尔量的八羰基二钴处理1，分别生成复合物[HSiMe2C≡CSiMe2H]Co2(CO)6和[HSiMe2C≡CSiMe2Co(CO)4]Co2(CO)6。还研究了二甲基(苯乙炔基)硅烷及其同类物与Co2(CO)8的反应。
• Hydrosilylation reactions of bis(dimethylsily)acetylenes: A potential route to novel σ- and π-conjugated polymers
  作者：David Y. Son、Daniel Bucca、Teddy M. Keller

  DOI：10.1016/0040-4039(96)00095-0

  日期：1996.3

  Chloroplatinic acid catalyzes hydrosilylation reactions between bis(dimethylsilyl)acetylenes and simple aromatic monoethynyl compounds, yielding styrenic derivatives. Reactions of the bis(dimethylsilyl)acetylenes with aromatic diethynyl compounds yield conjugated short chain oligomers.

  氯铂酸催化双（二甲基甲硅烷基）乙炔与简单的芳香族单乙炔基化合物之间的氢化硅烷化反应，生成苯乙烯衍生物。双（二甲基甲硅烷基）乙炔与芳族二乙炔基化合物的反应产生共轭短链低聚物。
• Si−H Bond Activation of Alkynylsilanes by Group 4 Metallocene Complexes
  作者：Martin Lamač、Anke Spannenberg、Wolfgang Baumann、Haijun Jiao、Christine Fischer、Sven Hansen、Perdita Arndt、Uwe Rosenthal

  DOI：10.1021/ja910527w

  日期：2010.3.31

  investigated. Reactions of the alkynylsilanes R(1)C(2)SiR(2)(2)H (R(1) = SiMe(3), R(2) = Me, 1; R(1) = SiMe(3), R(2) = Ph, 2; R(1) = SiMe(2)H, R(2) = Me, 5) with Cp(2)TiMe(2) (Cp = eta(5)-cyclopentadienyl) resulted, upon methyl group transfer to the silyl group, in the previously described titanocene alkyne complexes Cp(2)Ti(R(1)C(2)SiR(2)(2)R(3)) (R(1) = Me(3)Si, R(2) = R(3) = Me, 3; R(1) = HMe(2)Si, R(2) =

  研究了不同取代的炔基硅烷对选定的第 4 族金属茂配合物的反应性。炔基硅烷的反应 R(1)C(2)SiR(2)(2)H (R(1) = SiMe(3), R(2) = Me, 1; R(1) = SiMe(3), R(2) = Ph, 2; R(1) = SiMe(2)H, R(2) = Me, 5) 与 Cp(2)TiMe(2) (Cp = eta(5)-环戊二烯基)，在甲基转移到甲硅烷基后，在前面描述的二茂钛炔烃配合物中 Cp(2)Ti(R(1)C(2)SiR(2)(2)R(3)) (R(1) = Me( 3)Si, R(2) = R(3) = Me, 3; R(1) = HMe(2)Si, R(2) = R(3) = Me, 6) 或未报道的络合物 4 (R (1) = Me(3)Si，R(2) = Ph，R(3) = Me)。Cp(2)TiCl(2)/n-BuLi 系统产生炔配合物 6
• Silacyclopropenes
  作者：Dietmar Seyferth、Dennis C. Annarelli、Steven C. Vick

  DOI：10.1016/0022-328x(84)80461-1

  日期：1984.9

  The thermal decomposition of hexamethylsilirane in the presence of selected disubstituted acetylenes (Me3SiCCSiMe3), Me2HSiCCSiMe2H, Me3SiCCCH3, Me3SiCCCMe3, Me3CCCCH3) resulted in Me2Si addition to the CC bonds to give the respective silacyclopropenes. These are thermally stable but are extremely reactive toward atmospheric oxygen and moisture and react readily with methanol and ethanol at room

  hexamethylsilirane在选定的二取代的乙炔的存在（Me中热分解3 SiCCSiMe 3）中，Me 2 HSiCCSiMe 2 H，我3 SiCCCH 3中，Me 3 SiCCCMe 3中，Me 3 CCCCH 3）导致在CC键上加成Me 2 Si，得到相应的硅杂环丙烯。它们具有热稳定性，但对大气中的氧气和湿气具有极强的反应性，并且在室温下容易通过SiC（环）键断裂与甲醇和乙醇反应。很高的领域29Si NMR共振（-87至-106 ppm）是硅环丙烯环的特征。