十一烷酰三甲基硅烷 | 107399-10-0

• 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: 十一烷酰三甲基硅烷
• 英文名称: undecanoyltrimethylsilane
• 英文别名: Undecanoyl-trimethylsilane；1-trimethylsilylundecan-1-one
• CAS: 107399-10-0
• 化学式: C₁₄H₃₀OSi
• 分子量: 242.477
• InChiKey: BCNIRQJGZGNWFT-UHFFFAOYSA-N

物化性质

• 沸点：
  70-75 °C(Press: 0.15 Torr)
• 密度：
  0.828±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.96
• 重原子数：
  16
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.93
• 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：

  十一烷酰三甲基硅烷 在 tetrabutylammonium tetrafluoroborate 、 水 作用下， 以 二氯甲烷 为溶剂， 以92%的产率得到十一烷酸
  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：

  癸基溴 在 phosphate buffer 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 1.0h， 生成 十一烷酰三甲基硅烷
  参考文献：
  名称：

  有机合成中的新方法和试剂。62三甲基甲硅烷基重氮甲烷：一种方便的制备酰基硅烷的试剂

  摘要：

  三甲基甲硅烷基重氮甲烷的锂盐与烷基卤化物平稳反应，生成易于被间氯过苯甲酸（m-CPBA）氧化的α-三甲基甲硅烷基重氮烷烃，以高收率得到相应的酰基硅烷（α-酮硅烷）。

  DOI：

  10.1016/s0040-4039(00)84433-0

文献信息

• 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
• Redox selective reactions of organo-silicon and -tin compounds
  作者：Jun-ichi Yoshida、Keiji Nishiwaki

  DOI：10.1039/a803343i

  日期：——

  The C-Si and C-Sn sigma orbitals are higher in energy than C-H or C-C sigma orbitals, and therefore can interact with neighboring pi systems, non-bonding orbitals of heteroatoms, and other sigma systems such as those of C-Si and C-Sn, Such interactions cause an increase of the HOMO level which in turn favors electron transfer. On the basis of this effect various types of redox selective reactions of organo-silicon and -tin compounds have been developed.
• YOSHIDA, JUN-ICHI;MATSUNAGA, SHIN-ICHIRO;ISHICHI, YUJI;MAEKAWA, TSUYOSHI;+, J. ORG. CHEM., 56,(1991) N, C. 1307-1309
  作者：YOSHIDA, JUN-ICHI、MATSUNAGA, SHIN-ICHIRO、ISHICHI, YUJI、MAEKAWA, TSUYOSHI、+

  DOI：——

  日期：——
• AOYAMA, TOYOHIKO;SHIOIRI, TAKAYUKI, TETRAHEDRON LETT., 1986, 27, N 18, 2005-2006
  作者：AOYAMA, TOYOHIKO、SHIOIRI, TAKAYUKI

  DOI：——

  日期：——