(Z)-1-(trimethylsilyl)-3,3-dimethyl-1-butene | 26567-95-3

• 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
• 英文名称: (Z)-1-(trimethylsilyl)-3,3-dimethyl-1-butene
• 英文别名: (3,3-dimethyl-but-1-en-c-yl)-trimethyl-silane；(Z)-3,3-Dimethylbut-1-en-1-yl-(trimethyl)-silan；cis-1-Trimethylsilyl-3,3-dimethyl-buten-(1)；cis-1-Trimethylsilyl-3.3-dimethyl-buten-(1)；1-Trimethylsilyl-3,3-dimethyl-buten-(1c)；cis-1-Trimethylsilyl-3-dimethylbuten-1；[(Z)-3,3-dimethylbut-1-enyl]-trimethylsilane
• CAS: 26567-95-3
• 化学式: C₉H₂₀Si
• 分子量: 156.343
• InChiKey: BRIDLWZGGDIJRM-FPLPWBNLSA-N

物化性质

• 沸点：
  80-84 °C(Press: 97 Torr)
• 密度：
  0.757±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.47
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  (Z)-1-(trimethylsilyl)-3,3-dimethyl-1-butene 在 N-碘代丁二酰亚胺 作用下， 以 乙腈 为溶剂， 以65%的产率得到(Z)-1-iodo-3,3-dimethylbut-1-ene
  参考文献：
  名称：

  A mild preparation of vinyliodides from vinylsilanes

  摘要：

  A new method for the synthesis of vinyliodides from vinylsilanes is presented. Using N-iodiosuccinimide in acetonitrile or acetonitrile/monochloroacetonitrile, this transformation is cleanly effected at room temperature under virtually neutral conditions. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4039(96)02000-x
• 作为产物：
  描述：

  [(Z)-1-dicyclohexylboranyl-3,3-dimethylbut-1-enyl]-trimethylsilane 在 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 (Z)-1-(trimethylsilyl)-3,3-dimethyl-1-butene
  参考文献：
  名称：

  A simple synthesis of B-2-(1-trimethylsilyl-1-alkyl)-1,3,2-dioxaborinanes. Isolation and selective oxidation to 1-trimethylsilyl-1-alkanols

  摘要：

  (Z)-1-Trimethylsilyl-1-alkenes easily prepared by the hydroboration of the corresponding 1-trimethylsilyl-1-alkynes followed by protonolysis with acetic acid, readily react with dibromoborane-methyl sulfide complex in dichloromethane for 6 h. The resulting solution is then treated with 1,3-propane diol in a 1:1 mixture of dichloromethane and n-pentane at 0degreesC for half an hour to provide the corresponding gem-dimetalloalkanes containing boron and silicon. These alpha-trimethylsilylalkylboronate esters are purified by vacuum distillation in high yields (72-84%) and the structures of these novel intermediates are further confirmed by selective oxidation with alkaline hydrogen peroxide to provide the corresponding alcohols containing trimethylsilyl group. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01750-7

文献信息

• The stereoselective conversion of vinylsilanes to γ-substituted allylsilanes via higher order cuprates
  作者：John A. Soderquist、Braulio Santiago

  DOI：10.1016/s0040-4039(00)76172-7

  日期：1989.1

  Pure cis-vinylsilanes are efficiently converted to cis-epoxysilanes which react smoothly with Li2Cu(CN)(CH2TMS)2 to provide the corresponding erythro disilylated alcohol, in excellent yield and isomeric purity. Elimination of the elements of TMSOH affords either the pure cis- or trans- γ-substituted allylsilanes, under basic or acidic conditions, respectively.

  纯的顺式乙烯基硅烷可以有效地转化为顺式环氧硅烷，可以与Li 2 Cu（CN）（CH 2 TMS）2平稳反应，从而以优异的收率和异构纯度提供相应的赤型二烯丙基化醇。消除TMSOH的元素分别在碱性或酸性条件下提供了纯的顺式或反式-γ-取代的烯丙基硅烷。
• Alkynylsilanes to cis-vinylsilanes via hydroboration
  作者：John A. Soderquist、Braulio Santiago

  DOI：10.1016/s0040-4039(00)97818-3

  日期：1990.1

  New general non-oxidative procedures have been developed for the conversion of 1-trimethylsilylacetylenes to pure cis-1-trimethylsilylalkenes via hydroboration/protonolysis.

  已经开发出新的通用的非氧化方法，用于通过氢硼化/质子分解将1-三甲基甲硅烷基乙炔转化为纯的顺式-1-三甲基甲硅烷基链烯。
• Effect of steric bulk on the absolute reactivity of allene oxides
  作者：Mark W. Konecny、Norman P. Schepp

  DOI：10.1039/b910887d

  日期：——

  fluorenylidene allene oxides were generated photochemically from appropriately substituted fluorenol derivatives in 2,2,2-trifluoroethanol (TFE) in order to assess the affect of steric bulk on the absolute reactivity of the allene oxides. The absolute reactivities of the allene oxides were measured using nanosecond laser flash photolysis, and were found to change little in TFE upon going from α-methyl to

  α-烷基取代的芴基丙二烯氧化物是由适当取代的光化学生成的 芴醇 的衍生 2,2,2-三氟乙醇（TFE），以评估空间体积对丙二烯氧化物绝对反应性的影响。使用纳秒激光闪光光解法测量丙二烯氧化物的绝对反应性，发现从α-甲基到α-丁基再到α-叔丁基时，TFE的变化很小。然而，所有三种α-烷基取代的氧化烯均比α-氢衍生物具有更高的反应性，这表明空间体积并未导致反应性降低，而这通常是在其他氧化烯中发现的。通过详细检查由产物研究确定的这些烯丙氧化物的反应，可以解释芴基烯丙氧化物的相反的反应性。
• Organometallic compounds of Group III. XIX. Regiospecificity and stereochemistry in the hydralumination of unsymmetrical acetylenes. Controlled cis or trans reduction of 1-alkynyl derivatives
  作者：John J. Eisch、Michael W. Foxton

  DOI：10.1021/jo00822a012

  日期：1971.11
• A highly stereoselective synthesis of vinyl bromides and chlorides via disubstituted vinylsilanes
  作者：R. Bryan Miller、Glenn McGarvey

  DOI：10.1021/jo00417a006

  日期：1978.11