trimethyl(4-methylphenethyl)silane | 27490-76-2

• 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: trimethyl(4-methylphenethyl)silane
• 英文别名: Trimethyl-(4-methyl-phenaethyl)-silan；Trimethyl-[2-(4-methylphenyl)ethyl]silane；trimethyl-[2-(4-methylphenyl)ethyl]silane
• CAS: 27490-76-2
• 化学式: C₁₂H₂₀Si
• 分子量: 192.376
• InChiKey: FATVSGAWWXQHLR-UHFFFAOYSA-N

物化性质

• 沸点：
  222-224 °C(Press: 745 Torr)
• 密度：
  0.864 g/cm3

计算性质

• 辛醇/水分配系数(LogP)：
  3.88
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  trimethyl(4-methylphenethyl)silane 、 (溴-二氯甲基)-苯基汞 生成 (3,3-Dichloro-2-p-tolyl-propyl)-trimethyl-silane
  参考文献：
  名称：

  Halomethylmetal compounds. XXXIV. Insertion of phenyl(bromodichloromethyl)mercury-derived dichlorocarbene into carbon-hydrogen bonds. Tetraalkylsilicon and tetraalkyltin compounds

  摘要：

  DOI：

  10.1021/ja00717a043
• 作为产物：
  描述：

  甲基碘化镁 、 (2-p-tolylethyl)trichlorosilane 生成 trimethyl(4-methylphenethyl)silane
  参考文献：
  名称：

  Petrow et al., Zhurnal Obshchei Khimii, 1955, vol. 25, p. 2469,2472;engl.Ausg.S.2357,2359

  摘要：

  DOI：

文献信息

• Stereoselective one-pot synthesis of vinylsilanes from aromatic aldehydes
  作者：Man Lung Kwan、Chiu W Yeung、Kerry L Breno、Kenneth M Doxsee

  DOI：10.1016/s0040-4039(00)02271-1

  日期：2001.2

  Vinylsilanes serve as convenient vinyl anion equivalents, but procedures for their stereoselective synthesis from aldehydes are scarce. A variety of aromatic aldehydes are converted to the corresponding vinylsilanes in a one-pot procedure involving the addition of (trimethylsilylmethyl)lithium to the aldehyde followed by treatment with Cp2TiCH2·AlMe2Cl (‘Tebbe's reagent’). Halide and alkoxide substituents

  乙烯基硅烷可以用作方便的乙烯基阴离子当量，但是从醛中进行立体选择合成的方法却很少。通过一锅法将多种芳族醛转化为相应的乙烯基硅烷，包括在醛中添加（三甲基甲硅烷基甲基）锂，然后用Cp 2 TiCH 2 ·AlMe 2 Cl（'Tebbe's agent '）处理。卤化物和烷氧基取代基是可容忍的，并且（E）-乙烯基硅烷仅以高收率形成。
• Formal Hydrotrimethylsilylation of Styrenes with Anti-Markovnikov Selectivity Using Hexamethyldisilane
  作者：Xin Wang、Zhi-Xiang Yu、Wen-Bo Liu

  DOI：10.1021/acs.orglett.2c03170

  日期：2022.12.9

  A combination of CsF and hexamethyldisilane in DMSO enabling an anti-Markovnikov formal hydrotrimethylsilylation of styrenes is reported. Mechanistic investigations detail the reaction pathways, including in situ generation of a silyl anion, the addition of this silyl anion onto the alkene to form a carbanion, and this carbanion is then protonated by DMSO. The choice of the solvent to match its reactivity

  据报道，CsF 和六甲基乙硅烷在 DMSO 中的组合能够实现苯乙烯的反马尔可夫尼科夫形式氢化三甲基硅烷化。机理研究详细说明了反应途径，包括原位生成甲硅烷基阴离子，将这种甲硅烷基阴离子加成到烯烃上形成负碳离子，然后该负碳离子被 DMSO 质子化。选择溶剂以匹配其与负碳离子和甲硅烷基阴离子的反应性是该反应成功的关键。
• Synthesis of (E)-alkenes via hydroindation of CC in InCl3–NaBH4 system
  作者：Chunyan Wang、Lei Yan、Zhiguo Zheng、Deyu Yang、Yuanjiang Pan

  DOI：10.1016/j.tet.2006.05.066

  日期：2006.8

  In InCl3-NaBH4-MeCN system, terminal aryl alkynes could couple with aryl iodides and bromides to give disubstituted alkenes via hydroindation of C equivalent to C. In the similar way, (E)-alkenylsilanes were synthesized via reduction of alkynylsilanes in tetrahydrofuran (THF) in high yields. The processes showed high regio- and stereoselectivity. (c) 2006 Elsevier Ltd. All rights reserved.