1-三乙基甲硅烷基乙酮 | 30608-91-4

• 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
• 中文名称: 1-三乙基甲硅烷基乙酮
• 英文名称: acetyltriethylsilane
• 英文别名: 1-(triethylsilyl)ethan-1-one；1-triethylsilylethanone
• CAS: 30608-91-4
• 化学式: C₈H₁₈OSi
• 分子量: 158.316
• InChiKey: DDUXYGXCOGALBF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.62
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-三乙基甲硅烷基乙酮 在 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以93%的产率得到1-(triethylsilyl)ethanol
  参考文献：
  名称：

  1- and 2-(trialkylsilyl)ethanols: new silyl reagents from tin, lithium, and boron chemistry

  摘要：

  DOI：

  10.1021/jo00278a014
• 作为产物：
  描述：

  (1-methoxyvinyl)triethylsilane 在 盐酸 作用下， 以 丙酮 为溶剂， 反应 1.5h， 以93%的产率得到1-三乙基甲硅烷基乙酮
  参考文献：
  名称：

  1- and 2-(trialkylsilyl)ethanols: new silyl reagents from tin, lithium, and boron chemistry

  摘要：

  DOI：

  10.1021/jo00278a014

文献信息

• Photo Click Reaction of Acylsilanes with Indoles
  作者：Constantin Stuckhardt、Maren Wissing、Armido Studer

  DOI：10.1002/anie.202101689

  日期：2021.8.16

  as documented by the clicking of carbohydrates with indole alkaloids. The method is also applicable to the conjugation of polymer chains. The linking acetal moiety can be readily cleaved and it is also shown that wavelength-selective coupling and cleavage with acyl silanes bearing a second photoactive moiety is possible. This is documented by a successful polymerization/depolymerization sequence and

  报道了酰基硅烷与吲哚的光介导偶联。这种光点击反应在温和条件 (415 nm) 下发生，主要以定量产率进行，并通过光介导的硅氧卡宾生成和随后的吲哚-NH 插入提供稳定的硅烷化 N,O-缩醛。我们证明，这种非常有效且完全原子经济的偶联过程可以应用于共轭复杂系统，正如碳水化合物与吲哚生物碱的点击所记录的那样。该方法也适用于聚合物链的共轭。连接缩醛部分可以容易地裂解，并且还表明与带有第二光活性部分的酰基硅烷的波长选择性偶联和裂解是可能的。这是通过成功的聚合/解聚序列和聚合物折叠/展开过程来记录的。
• Low-Temperature Intermolecular Addition of RCF2Li Compounds to Various Carbonyl Electrophiles for a Practical Synthesis of CF2-Containing Building Blocks
  作者：Mélanie Decostanzi、Jean-Marc Campagne、Eric Leclerc

  DOI：10.1055/s-0035-1562786

  日期：2016.10

  compounds. In contrast with existing methods that use more stable, but less reactive, organometallic species, there is efficient addition to esters, lactones and poorly reactive ketones. The addition of various RCF2Li compounds to a wide range of carbonyl electrophiles (aldehydes, ketones, acylsilanes, esters, and lactones) is reported. The reaction proceeds at very low temperature under Barbier conditions

  本文致力于纪念Jean F. Normant教授，并赞扬他在有机金属化学领域的杰出贡献。 抽象的 据报道，将各种RCF 2 Li化合物添加到各种羰基亲电子试剂（醛，酮，酰基硅烷，酯和内酯）中。该反应在巴比尔条件下在非常低的温度下通过与相应的RCF 2 Br化合物的Br / Li交换进行。与使用更稳定，但反应性较低的有机金属物质的现有方法相比，酯，内酯和反应性较差的酮类均有效添加。 据报道，将各种RCF 2 Li化合物添加到各种羰基亲电子试剂（醛，酮，酰基硅烷，酯和内酯）中。该反应在巴比尔条件下在非常低的温度下通过与相应的RCF 2 Br化合物的Br / Li交换进行。与使用更稳定，但反应性较低的有机金属物质的现有方法相比，酯，内酯和反应性较差的酮类均有效添加。
• Four‐Component Strain‐Release‐Driven Synthesis of Functionalized Azetidines
  作者：Jasper L. Tyler、Adam Noble、Varinder K. Aggarwal

  DOI：10.1002/anie.202214049

  日期：2022.12.23

  A multicomponent [1,2]-Brook rearrangement/strain-release-driven anion relay sequence and its application to the modular synthesis of substituted azetidines is described. Three electrophilic coupling partners, whose identities can be individually varied, were added sequentially to the highly strained fragment azabicyclo[1.1.0]butyl-lithium to access a diverse compound library.

  描述了多组分 [1,2]-Brook 重排/应变释放驱动的阴离子中继序列及其在取代氮杂环丁烷的模块化合成中的应用。三个亲电子偶联伙伴，其身份可以单独变化，依次添加到高度应变的片段氮杂双环 [1.1.0] 丁基锂中，以访问多样化的化合物库。
• Transition‐Metal‐Free Synthesis of Enantioenriched Tertiary and Quaternary α‐Chiral Allylsilanes
  作者：Rubén Pérez Sevillano、Franck Ferreira、Olivier Jackowski

  DOI：10.1002/chem.202302227

  日期：2023.10.23

  Enantioenriched tertiary and quaternary α-chiral allylsilanes have been obtained by metal-free asymmetric allylic alkylation of γ-substituted primary allylic bromides with primary alkyl Grignard reagents activated by a chiral Alexakis-type NHC ligand.

  对映体富集的叔和季α-手性烯丙基硅烷是通过手性Alexakis型NHC配体活化的伯烷基格氏试剂对γ-取代的伯烯丙基溴化物进行无金属不对称烯丙基烷基化而获得的。
• Facile synthesis of a novel class of organometalloid-containing ligands, the sila-β-diketones: preparation and physical and structural characterization of the copper(II) complexes, Cu[R′C(O)CHC(O)SiR3]2
  作者：Kulbinder K Banger、Silvana C Ngo、Seiichiro Higashiya、Rolf U Claessen、Kenneth S Bousman、Poay N Lim、Paul J Toscano、John T Welch

  DOI：10.1016/s0022-328x(03)00393-0

  日期：2003.7

  The substitution of a carbon atom by silicon provides an attractive, novel approach to modification of the thermal stability and volatility of metal-organic chemical vapor deposition precursors supported by beta-diketonate ancillary ligands. The low temperature reaction of the lithium enolates of acetyltrialkylsilanes with acyl chlorides affords the sila-beta-diketones, R'C(O)CH2C(O)SiR3 (R' = Me, Et, n-Pr, i-Pr, n-Bu, i-Bu, s-Bu, t-Bu; SiR3 = SiMe3, SiEt3, SiMe2(t-Bu), SiMe2(t-hexyl), Si(i-Pr)A in good yields. Multinuclear NMR studies suggest that the sila-beta-diketones exist as the enolic tautomer with a vinylsilane isomeric structure. Homoleptic Cu(II) sila-beta-diketonate complexes were prepared in a first pass study to evaluate how precursor performance is affected by modulation of the peripheral substituents in the ligands. Thermal analyses, (TGA, DSC) show that the silylated Cu(II) precursors (SiR3 = SiMe3; R' = t-Bu or i-Bu) have greater volatility than the corresponding carbon analogues. Some of the new Cu(11) complexes exist as liquids or low melting solids, which are preferred states for industrial deposition processes. X-ray diffraction studies of selected copper complexes showed them to have typical, square planar geometry; calculations of molecular volumes suggest that packing in the solid-state is less efficient for the silicon-containing complexes than for the non-silylated analogues. (C) 2003 Elsevier Science B.V. All rights reserved.