2-cyclohexyl-1-trimethylsilylethanone | 78980-82-2

• 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: 2-cyclohexyl-1-trimethylsilylethanone
• 英文别名: (cyclohexylacetyl)trimethylsilane
• CAS: 78980-82-2
• 化学式: C₁₁H₂₂OSi
• 分子量: 198.381
• InChiKey: AJGKUKHYZSIVSY-UHFFFAOYSA-N

物化性质

• 沸点：
  67 °C(Press: 1 Torr)
• 密度：
  0.876±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 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：

  2-cyclohexyl-1-trimethylsilylethanone 在 盐酸 、 tetrabutylammonium tetrafluoroborate 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 0.17h， 生成 1-环己基乙腈
  参考文献：
  名称：

  Electrochemical oxidation of acylsilanes and their tosylhydrazones

  摘要：

  Oxidation potentials of acylsilanes were found to be much less positive than those of ketones and aldehydes. The effect of silicon is attributed to the rise of the HOMO level by the interaction between the C-Si sigma-orbital and the nonbonding p orbital of the carbonyl oxygen which in turn favors the electron transfer. Preparative electrochemical oxidation of acylsilanes proceeded smoothly, giving rise to facile cleavage of the C-Si bond and the introduction of nucleophiles such as alcohols, water, and carbamates onto the carbonyl carbon. Electrochemical properties of tosylhydrazones of acylsilanes were also investigated. A decrease in oxidation potential of tosylhydrazones caused by silyl substitution was found to be smaller than that for carbonyl compounds. Preparative electrochemical oxidation of tosylhydrazones of acylsilanes gave the corresponding nitriles with consumption of a catalytic amount of electricity.

  DOI：

  10.1021/jo00044a023
• 作为产物：
  描述：

  2-环己基乙炔基(三甲基)硅烷 在 十二/十四烷基二甲基氧化胺 、 dimethyl sulfide borane 、 水 作用下， 以83%的产率得到2-cyclohexyl-1-trimethylsilylethanone
  参考文献：
  名称：

  A Convenient Synthesis of Acylsilanes via Hydroboration-Oxidation of Silylacetylenes

  摘要：

  DOI：

  10.1055/s-1981-29419

文献信息

• Vinyldisilanes as masked acylsilanes
  作者：David M. Hodgson、Paul J. Comina

  DOI：10.1039/cc9960000755

  日期：——

  The synthesis of acylsilanes 3 from vinyldisilanes 1 by epoxidation and treatment of the resulting epoxydisilanes 2 with H2SO4 in MeOH is described.

  描述了通过环氧化和用硫酸在甲醇中处理得到的环氧双硅烷2，将乙烯基双硅烷1转化为酰基硅烷3的合成方法。
• A Novel One-Pot Synthesis of α-Substituted 2-Alkenoylsilanes from Enolizable Acylsilanes
  作者：Bianca Flavia Bonini、Mauro Comes-Franchini、Andrea Mazzanti、Germana Mazzanti、Alfredo Ricci、Paolo Zani

  DOI：10.1055/s-1995-3907

  日期：1995.3

  α-Substituted 2-alkenoylsilanes can be easily prepared by a simple method based on a one-pot Mannich reaction of enolizable acylsilanes.

  通过一种基于可烯化酰基硅烷的一锅曼尼希反应的简单方法，可以轻松制备δ-取代的 2-烯酰硅烷。
• Hodgson, David M.; Comina, Paul J.; Drew, Michael G. B., Journal of the Chemical Society. Perkin transactions I, 1997, # 16, p. 2279 - 2289
  作者：Hodgson, David M.、Comina, Paul J.、Drew, Michael G. B.

  DOI：——

  日期：——
• A new method for the synthesis of acylsilanes via one-carbon homologation of aldehydes
  作者：Junichi Yoshida、Shinichiro Matsunaga、Yuji Ishichi、Tsuyoshi Maekawa、Sachihiko Isoe

  DOI：10.1021/jo00003a072

  日期：1991.2
• Electrochemical oxidation of acylsilanes
  作者：Jun-ichi Yoshida、Shin-ichiro Matsunaga、Sachihiko Isoe

  DOI：10.1016/s0040-4039(01)93768-2

  日期：1989.1