5-methoxy-5-(trimethylsilyl)pentadecane | 142981-63-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-methoxy-5-(trimethylsilyl)pentadecane
• 英文别名: 5-Methoxypentadecan-5-yl(trimethyl)silane
• CAS: 142981-63-3
• 化学式: C₁₉H₄₂OSi
• 分子量: 314.627
• InChiKey: JNDKGNJFJPUKEV-UHFFFAOYSA-N

物化性质

• 沸点：
  348.5±15.0 °C(Predicted)
• 密度：
  0.818±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.97
• 重原子数：
  21
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  5-methoxy-5-(trimethylsilyl)pentadecane 在 四乙基对甲苯磺酸铵 作用下， 以 甲醇 为溶剂， 以81%的产率得到十五烷-5-酮
  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：

  十一烷酰三甲基硅烷 在 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.08h， 生成 5-methoxy-5-(trimethylsilyl)pentadecane
  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

文献信息

• Electrochemical oxidation of acylsilanes and their tosylhydrazones
  作者：Junichi Yoshida、Masanori Itoh、Shinichiro Matsunaga、Sachihiko Isoe

  DOI：10.1021/jo00044a023

  日期：1992.8

  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.