1-phenyl-3-(trimethylsilyl)-2-(trimethylsilylmethyl)propene | 201344-76-5

• 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: 1-phenyl-3-(trimethylsilyl)-2-(trimethylsilylmethyl)propene
• 英文别名: Silane, [2-(phenylmethylene)-1,3-propanediyl]bis[trimethyl-；trimethyl-[3-phenyl-2-(trimethylsilylmethyl)prop-2-enyl]silane
• CAS: 201344-76-5
• 化学式: C₁₆H₂₈Si₂
• 分子量: 276.569
• InChiKey: HOSKDOFSBAKADW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.75
• 重原子数：
  18
• 可旋转键数：
  5
• 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：

  1-phenyl-3-(trimethylsilyl)-2-(trimethylsilylmethyl)propene 在 4-甲基苯磺酸吡啶 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 48.0h， 以85%的产率得到2-Benzyl-3-trimethylsilylpropene
  参考文献：
  名称：

  Preparation of 2-trimethylsilylmethyl-1-alkene; cross-coupling and protodesilylation sequence from 1,1-dibromo-1-alkene

  摘要：

  A new method for the preparation of exomethylene type allylsilane is described. Selective mono-protodesilylation of 1-trimethylsityl-2-trimethylsilylmethyl-2-alkenes 2 with PPTS afforded 2-trimethylsilylmethyl-l-alkeiles 4 in excellent yields. Since the resulting allylsilanes 4 possess an exomethylene unit, the reactions of 4 with carbonyl compounds in the presence of Lewis acids gave the corresponding product 7 having an exomethylene unit in excellent yields. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.12.044
• 作为产物：
  描述：

  2-甲基-3-苯基-1-丙烯 在 正丁基锂 、 四甲基乙二胺 作用下， 以 正己烷 为溶剂， 反应 16.0h， 生成 1-phenyl-3-(trimethylsilyl)-2-(trimethylsilylmethyl)propene
  参考文献：
  名称：

  Reactions of the Lithium Salts of the Tribenzylidenemethane Dianion, Diphenylacetone Dianion, and Related Compounds

  摘要：

  Potentially synthetically useful reactions of the dilithium salts of the title dianions have been investigated, Electrophilic quenching with a variety of reagents usually leads to the expected products in good yield. Quenching the diphenylacetone dianion with 1 equiv of trimethylchlorosilane, however, gives a good yield of 1,3-diphenylallene obtained by formal elimination of a trimethylsiloxy anion from an intermediate monoquenched monoanion salt. NMR studies, however, do not reveal the intermediacy of the 1,3-diphenyl-2-(trimethylsiloxy)allyl anion but rather suggest that the initial reaction site is at carbon, rather than oxygen, Oxidation of the dianions leads either to ring closure or dimerization for the tribenzylidenemethane dianion and to dimerization for the diphenylacetone dianion. The dimerization reactions are stereospecific, both with respect to the two new stereocenters produced and for the double bonds of the bis-silyl enol ether products if the dimeric bis-enolate dianion products are quenched with trimethylchlorosilane.

  DOI：

  10.1021/jo971113c

文献信息

• β,β-Disilylated Sulfones as Versatile Building Blocks in Organic Chemistry - A New Sulfonyl Carbanion Transmetalation
  作者：Ullrich Jahn、Bertrand Puget

  DOI：10.1055/s-0030-1258772

  日期：2010.10

  1,3-Bis(trimethylsilyl)propyl phenyl sulfone undergoes, in contrast to all reported sulfones bearing α-hydrogen atoms, an initial ortho metalation to an aryllithium at low temperature, which transmetalates quantitatively to the corresponding α-sulfonyl organolithium intermediate. Both organolithiums react selectively with aldehydes to give the corresponding products in good to excellent yields with high selectivity.

  1,3-双(trimethylsilyl)丙基苯磺酸酯与所有报告的具有α-氢原子的磺酰胺相比，在低温下经历初步的邻位金属化，形成芳基锂化合物，然后定量转金属化为相应的α-磺酰基有机锂中间体。两种有机锂化合物与醛类选择性反应，生成相应的产物，产率良好到优异，选择性高。