1-(trimethylsilyl)-3-phenyl-1-(trimethylsiloxy)-1-propene | 63578-13-2

• 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: 1-(trimethylsilyl)-3-phenyl-1-(trimethylsiloxy)-1-propene
• 英文别名: 1-trimethylsiloxy-1-tri methylsilyl-3-phenyl-1-propene；3-phenyl-1-trimethylsiloxy-1-trimethylsilylpropene；Trimethyl{3-phenyl-1-[(trimethylsilyl)oxy]prop-1-en-1-yl}silane；trimethyl-(3-phenyl-1-trimethylsilyloxyprop-1-enyl)silane
• CAS: 63578-13-2
• 化学式: C₁₅H₂₆OSi₂
• 分子量: 278.542
• InChiKey: SLEVEFSTVRTQOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.84
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 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：

  1-(trimethylsilyl)-3-phenyl-1-(trimethylsiloxy)-1-propene 在 溴 作用下， 以 四氯化碳 为溶剂， 以87%的产率得到2-bromo-3-phenylpropionyltrimethylsilane
  参考文献：
  名称：

  2-氯酰基三甲基硅烷与格氏试剂的反应。3-(三甲基甲硅烷基)-2-烷酮和2-(三甲基甲硅烷基)-1-烷醇的制备

  摘要：

  已经研究了 2-氯酰基三甲基硅烷与格氏试剂的反应。因此，用甲基碘化镁处理通过初始添加、随后去除氯阴离子和甲硅烷基的 1,2-重排得到相应的 3-(三甲基甲硅烷基)-2-烷酮。相比之下，反应用 2 当量的带有 β-氢的格利雅试剂进行，得到 2-（三甲基甲硅烷基）-1-烷醇，其中甲硅烷基羰基的初始还原，然后是这种重排，并将格利雅试剂加入到所得的 2 -(三甲基甲硅烷基)链烷醛已被提出。

  DOI：

  10.1246/bcsj.57.2167
• 作为产物：
  描述：

  S-phenyl 3-phenylpropanethioate 在 sodium 、 lithium diisopropyl amide 作用下， 反应 5.0h， 生成 1-(trimethylsilyl)-3-phenyl-1-(trimethylsiloxy)-1-propene
  参考文献：
  名称：

  Synthesis and reactivity of iron carbonyl complexes of α,β-unsaturated acyl silanes

  摘要：

  2-Trimethylsilyl-1-oxa-1,3-butadiene (7) reacts with Fe2(CO)9 to form an unstable tetracarbonyliron(0) complex (8) whereas 2-trimethylsilyl-4-phenyl-1-oxa-1,3-butadiene (9) and 2-(tert-butyldimethylsilyl)-4-phenyl-1-oxa-1,3-butadiene (20) react with Fe2(CO)9 to form highly stable crystalline tricarbonyliron(0) complexes (16) and (21). Complexes (16) and (21) both undergo acylation when reacted with methyl lithium under nitrogen to form gamma-ketoacylsilanes [(18) and (22)], but only complex (21) reacts with methyl lithium under carbon monoxide to give the tricarbonyl(vinylketene)iron(0) complex (23).

  DOI：

  10.1016/s0040-4020(01)90375-8

文献信息

• Conversion of Carbon-Sulfur Linkages into Carbon–Silicon Ones<i>via</i>Reductive Silylation. Preparation of Silyl Enol Ethers of Acyltrimethylsilanes
  作者：Isao Kuwajima、Akio Mori、Masahiro Kato

  DOI：10.1246/bcsj.53.2634

  日期：1980.9

  Reductive cleavage of carbon–sulfur linkages of silyl enol ethers of thiocarboxylic S-esters can be induced by treatment with sodium or potassium–sodium alloy in the presence of chlorotrimethylsilane, and the corresponding silyl enol ethers of acyltrimethylsilanes can be prepared in high yields.

  在三甲基氯硅烷存在下，用钠或钾钠合金处理可诱导硫代羧酸 S 酯硅基烯醇醚的碳硫键发生还原性裂解，并以高产率制备出相应的酰基三甲基硅烷硅基烯醇醚。
• Efficient method for the preparation of trimethylsilyl enol ethers of acyltrimethylsilanes
  作者：Isao Kuwajima、Masahiro Kato、Toshio Sato

  DOI：10.1039/c39780000478

  日期：——

  Treatment of trimethylsilyl enol ethers of benzenethiol esters with metallic sodium–trimethyl-chlorosilane affords the corresponding trimethylsilyl enol ethers of acyltrimethylsilanes in excellent yield.

  用金属钠-三甲基-氯硅烷处理苯硫醇酯的三甲基甲硅烷基烯醇醚，可以以优异的收率得到相应的酰基三甲基硅烷的三甲基甲硅烷基烯醇醚。
• Acylsilane chemistry. Synthesis of regio- and stereoisomerically defined enol silyl ethers using acylsilanes
  作者：Hans J. Reich、Ronald C. Holtan、Carsten Bolm

  DOI：10.1021/ja00170a026

  日期：1990.7
• Preparation of α, β-unsaturated acyltrimethylsilanes
  作者：Naoki Minami、Toru Abe、Isao Kuwajima

  DOI：10.1016/s0022-328x(00)84081-4

  日期：1978.1
• Diastereoselective aldol condensation of acylsilane silyl enol ethers with acetals
  作者：Mitsunori Honda、Wataru Oguchi、Masahito Segi、Tadashi Nakajima

  DOI：10.1016/s0040-4020(02)00787-1

  日期：2002.8

  Treatment of E- or Z-acylsilane silyl enol ethers derived from acylsilanes having an enolizable methylene proton with a mixture of aromatic aldehyde dimethyl acetals and TiCl4 in dichloromethane gives the corresponding 2,3-anti-3-methoxyacylsilanes in high d.e., independent of the geometry of double bond in acylsilane silyl enol ethers. On the other hand, E-acylsilane silyl enol ethers react with acetals of aliphatic aldehydes to afford the corresponding aldol adducts with syn-selectivity, while the reaction of Z-isomers provides the products with anti-selectivity. (C) 2002 Elsevier Science Ltd. All rights reserved.