N-(methoxycarbonyl)-N-methylundecanamide | 125481-81-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-(methoxycarbonyl)-N-methylundecanamide
• 英文别名: Methyl methyl(undecanoyl)carbamate；methyl N-methyl-N-undecanoylcarbamate
• CAS: 125481-81-4
• 化学式: C₁₄H₂₇NO₃
• 分子量: 257.373
• InChiKey: XXYRKSGPJAUKLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  18
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  甲基甲基氨基甲酸酯 、 十一烷酰三甲基硅烷 在 4 A molecular sieve 、 tetrabutylammonium tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 以69%的产率得到N-(methoxycarbonyl)-N-methylundecanamide
  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
  作者：Jun-ichi Yoshida、Shin-ichiro Matsunaga、Sachihiko Isoe

  DOI：10.1016/s0040-4039(01)93768-2

  日期：1989.1