(E)-2-Methyl-1-(trimethylsiloxy)-1-butene | 53282-50-1

• 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: (E)-2-Methyl-1-(trimethylsiloxy)-1-butene
• 英文别名: (E)-2-methyl-1-trimethylsiloxy-1-butene；trimethyl-[(E)-2-methylbut-1-enoxy]silane
• CAS: 53282-50-1
• 化学式: C₈H₁₈OSi
• 分子量: 158.316
• InChiKey: BUNSMAVATPORPP-BQYQJAHWSA-N

物化性质

• 沸点：
  120 °C
• 密度：
  0.807±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.15
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-2-Methyl-1-(trimethylsiloxy)-1-butene 生成 [(E)-2-methylbut-1-enyl] trifluoromethanesulfonate
  参考文献：
  名称：

  APELOIG, YITZHAK;KARNI, M.;STANG, P. J.;FOX, D. P., J. AMER. CHEM. SOC., 1983, 105, N 14, 4781-4792

  摘要：

  DOI：
• 作为产物：
  描述：

  三甲基氯硅烷 、 2-甲基丙烯醛 、 甲基溴化镁 在 六甲基磷酰三胺 、 copper(I) bromide dimethylsulfide complex 作用下， 以 四氢呋喃 为溶剂， 反应 15.0h， 以60%的产率得到(E)-2-Methyl-1-(trimethylsiloxy)-1-butene
  参考文献：
  名称：

  催化和化学计量的有机铜试剂的氯硅烷加速共轭加成

  摘要：

  三烷基甲硅烷基氯化物，特别是与六甲基磷酰胺或4-二甲基氨基吡啶组合，可显着加速催化和化学计量的有机铜试剂在烯酮，烯醛和烯酸酯上的共轭加成，其中观察到很高的立体和化学选择性。

  DOI：

  10.1016/0040-4020(89)80064-x

文献信息

• Gmelin Handbuch der Anorganischen Chemie, Gmelin Handbook: F: PerFHalOrg.SVol.3, 6.2.3.1, page 48 - 120
  作者：

  DOI：——

  日期：——
• Unsaturated carbenes from primary vinyl triflates. I. Method and scope
  作者：Peter J. Stang、Michael G. Mangum、Dennis P. Fox、Peter Haak

  DOI：10.1021/ja00821a034

  日期：1974.7
• Stereochemistry of the fluoride catalyzed aldol reaction of enol silyl ethers. Evidence for another non-chelate transition state
  作者：Eiichi Nakamura、Shigeru Yamago、Daisuke Machii、Isao Kuwajima

  DOI：10.1016/s0040-4039(00)86713-1

  日期：——
• Simple diastereoselectivity of the aldol reaction of persubstituted enolates. Stereoselective construction of quaternary centers
  作者：Shigeru Yamago、Daisuke Machii、Eiichi Nakamura

  DOI：10.1021/jo00006a026

  日期：1991.3

  Simple diastereoselectivity of several important categories of aldol reactions of persubstituted enolates has been investigated for sterically least biased cyclic and acyclic ketone and aldehyde enolates, 1-4, and has been found to be useful for the stereoselective construction of quaternary carbon centers. The types of reactions examined involve the reaction of lithium, borinate, borate, trialkoxytitanium, trichlorotitanium, and zirconium (Cp2ZrCl) enolates, and the reactions of enol silyl ethers under high pressure, fluoride catalysis, and Lewis acid catalysis. In contrast to the less substituted metal enolates, uncatalyzed reactions of persubstituted metal enolates proceeded in a sense anticipated from the conventional Zimmerman-Traxler chair transition state (TS) model. The fluoride-catalyzed reaction of the cyclic enolate 1a showed stereoselectivity consistent with the open extended TS, while enolates 2a-4a showed anomalous behavior. The selectivity of the Lewis acid mediated aldol reaction of enol silyl ethers was found to be dependent on the Lewis acid used, and the BF3.Et2O-mediated reaction of 2a and 3a showed maximum selectivity in a sense predicted by the chair TS. The stereostructures of the aldols have been determined by single-crystal X-ray analysis or by chemical correlations.
• PRIETO, J. ANTONIO;SUAREZ, JUAN;LARSON, GERALD L., SYNTH. COMMUN., 18,(1988) N 3, 253-257
  作者：PRIETO, J. ANTONIO、SUAREZ, JUAN、LARSON, GERALD L.

  DOI：——

  日期：——