3-丁烯三乙氧基硅烷 | 57813-67-9

• 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: 3-丁烯三乙氧基硅烷
• 中文别名: 3-烯丁基三乙氧基硅烷；烯丁基三乙氧基硅烷；3-丁烯基三乙氧基硅烷
• 英文名称: 3-butenyltriethoxysilane
• 英文别名: but-3-enyl(triethoxy)silane
• CAS: 57813-67-9
• 化学式: C₁₀H₂₂O₃Si
• mdl: MFCD00069150
• 分子量: 218.368
• InChiKey: LUZRKMGMNFOSFZ-UHFFFAOYSA-N

物化性质

• 熔点：
  -80°C
• 沸点：
  64°C 6mm
• 密度：
  0,9 g/cm3
• 闪点：
  73°C

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  14
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• TSCA：
  No
• 危险类别码：
  R36/37/38
• 安全说明：
  S26,S36/37/39

反应信息

• 作为反应物：
  描述：

  3-丁烯三乙氧基硅烷 在 盐酸 、 dihydrogen hexachloroplatinate 、 水 作用下， 以 乙醇 、 苯 为溶剂， 反应 68.0h， 生成 2,2,7,7-tetraethoxy-2,7-disilaoxacycloheptane
  参考文献：
  名称：

  Cyclization Phenomena in the Sol−Gel Polymerization of α,ω-Bis(triethoxysilyl)alkanes and Incorporation of the Cyclic Structures into Network Silsesquioxane Polymers

  摘要：

  Intramolecular cyclizations during acid-catalyzed sol-gel polymerizations of alpha,omega-bis(triethoxysilyl)-alkanes substantially lengthen gel times for monomers with ethylene (1), propylene (2), and butylene (3) bridging groups. These cyclization reactions were found, using mass spectrometry and Si-29 NMR spectroscopy, to lead preferentially to monomeric and dimeric products based on six- and seven-membered disilsesquioxane rings. 1,2-Bis(triethoxysilyl)ethane (1) reacts under acidic conditions to give a bicyclic dimer (5) that is composed of two annelated seven-membered rings. Under the same conditions, 1,3-bis(triethoxysilyl)propane (2), 1,4-bis(triethoxysilyl)butane (3), and Z-1,4-bis(triethoxysilyl)but-2-ene (10) undergo an intramolecular condensation reaction to give the six- and seven-membered cyclic disilsesquioxanes 6, 7, and 11. Subsequently, these cyclic monomers slowly react to form the tricyclic dimers 8, 9, and 12. With NaOH as polymerization catalyst, these cyclic silsesquioxanes readily reacted to afford gels that were shown by CP MAS Si-29 NMR and infrared spectroscopies to retain some cyclic structures. Comparison of the porosity and microstructure of xerogels prepared from the cyclic monomers 6 and 7 with those of gels prepared directly from their acyclic precursors 2 and 3 indicates that the final pore structure of the xerogels is markedly dependent on the nature of the precursor. In addition, despite the fact that the monomeric cyclic disilsesquioxane species cannot be isolated from 1-3 under basic conditions due to their rapid rate of gelation, spectroscopic techniques also detected the presence of the cyclic structures in the resulting polymeric gels.

  DOI：

  10.1021/ja982751v
• 作为产物：
  描述：

  3,4-二氯-1-丁烯 生成 3-丁烯三乙氧基硅烷
  参考文献：
  名称：

  DESCHLER, ULRICH;KLEINSCHMIT, PETER;WOLFF, SIEGFRIED;TAN, EWE-HONG

  摘要：

  DOI：

文献信息

• Polyfunctional carbosilanes and organosilicon compounds. Synthesis via grignard reactions
  作者：Dalci J. Brondani、Roben J.P. Corriu、Sabar El Ayoubi、Joël J.E. Moreau、Michel Wong Chi Man

  DOI：10.1016/s0040-4039(00)60358-1

  日期：1993.3

  stable at low temperatures. At 20°C, the Grignard reagent underwent intermolecular condensation, providing a simple synthesis of cyclic carbosilanes derivatives. The cross-coupling reaction with organic halides also afforded a facile route to a variety of trifunctional organosilicon compounds.

  （三乙氧基甲硅烷基）甲基氯化镁的THF溶液在低温下稳定。在20°C时，格氏试剂进行了分子间缩合，从而简单地合成了环状碳硅烷衍生物。与有机卤化物的交叉偶联反应也提供了通往各种三官能有机硅化合物的简便途径。
• Method of preparing pure 3-butenyl triorganooxysilanes, the intermediate
  申请人：Degussa AG

  公开号：US05164501A1

  公开（公告）日：1992-11-17

  A method of preparing pure 3-butenyl triorgano oxysilanes, the intermediate products 3,4-dichlorobutyl triorgano oxysilanes and the use of the final products in rubber mixtures reinforced with silicic acid and vulcanizable with peroxides. 3,4-dichlorobutene-1 and trichlorosilane are used as initial products.

  一种制备纯3-丁烯基三有机氧基硅烷、中间产物3,4-二氯丁基三有机氧基硅烷以及最终产品在硅酸加强的橡胶混合物中使用的方法，并且可以用过氧化物硫化。3,4-二氯丁烯-1和三氯硅烷作为初始产品。
• Dirhodium(II)/DPPM Catalyzed 1,2-Hydrosilylation of Conjugated Dienes with Tertiary Silanes
  作者：Liqun Yang、Xiaoyu Wu、Wenkui Lu、Yan Lu、Zhaoguo Zhang

  DOI：10.1021/acs.orglett.4c00450

  日期：2024.3.22

  (bis(diphenylphosphanyl)methane) catalyzed regioselective 1,2-anti-Markovnikov hydrosilylation of conjugated dienes with various tertiary silanes gave homoallylic silanes in acetonitrile, which tolerate broad functional groups. Control experiments proved that no π-allyl transition metal intermediates were involved in this 1,2-anti-Markovnikov hydrosilylation. Dirhodium hydride species was observed in

  简单高效的Rh 2 (OAc) 4 /DPPM（双（二苯基膦酰基）甲烷）催化共轭二烯与各种叔硅烷的区域选择性1,2-反马尔可夫尼科夫硅氢加成反应，在乙腈中得到均烯丙基硅烷，其具有广泛的官能团。对照实验证明，没有π-烯丙基过渡金属中间体参与该1,2-反马尔可夫尼科夫氢化硅烷化。在氢化硅烷化过程中观察到氢化二铑物质，表明该反应涉及末端双键直接插入 Rh-H 键。
• [EN] PLATINUM METALLACYCLES COMPRISING N,P,OR AS RINGATOMS AND THEIR USE AS CATALYSTS IN 1,2-HYDROSILYLATION REACTIONS OF DIENES<br/>[FR] 1,2-HYDROSILYLATION DE DIÈNES
  申请人：HARVARD COLLEGE

  公开号：WO2014138113A3

  公开（公告）日：2014-12-04
• 1,2-Selective Hydrosilylation of Conjugated Dienes
  作者：Sarah E. Parker、Jonas Börgel、Tobias Ritter

  DOI：10.1021/ja5008596

  日期：2014.4.2

  Selective 1,2-hydrosilylation of 1,3-dienes is a challenging problem in transition metal catalysis. Butadiene, specifically, would be a useful substrate because 3-butenylsilane products have promise as superior coupling reagents for hybrid organic/inorganic materials synthesis. We report the first selective 1,2-hydrosilylation of conjugated dienes including butadiene. Hydrosilylation proceeds through a Pt(II/IV) cycle, and selectivity is generated at a hexacoordinate Pt(IV) complex that favors eta(2)-diene coordination and prevents pi-allyl complex formation.