Methyl [(trimethylsilyl)amino]acetate | 25688-72-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Methyl [(trimethylsilyl)amino]acetate
• 英文别名: methyl 2-(trimethylsilylamino)acetate
• CAS: 25688-72-6
• 化学式: C₆H₁₅NO₂Si
• 分子量: 161.276
• InChiKey: IXVIBJMDQXQASU-UHFFFAOYSA-N

物化性质

• 保留指数：
  971

计算性质

• 辛醇/水分配系数(LogP)：
  0.58
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,2,2,4,4,4-hexafluoro-1,3-dimethyl-1,3,2λ⁵,4λ⁵-diazadiphosphetidine 、 Methyl [(trimethylsilyl)amino]acetate 以 乙醚 为溶剂， 反应 30.0h， 以59%的产率得到methyl 2-[(2,2,4,4,4-pentafluoro-1,3-dimethyl-1,3,2λ5,4λ5-diazadiphosphetidin-2-yl)amino]acetate
  参考文献：
  名称：

  Fluordiazadiphosphetidine. 22. Mitt. Reaktionen von 2,2,2,4,4,4-Hexafluoro-1,3-dimethyl-1,3,2?5,4?5-diazadiphosphetidin mit silylierten Aminos�uren

  摘要：

  The interaction of silylated amino acids with hexafluorodiazadiphosphetidine was studied. With trimethlsilyl amino acid esters the substitution of one fluorine atom was accomplished, whereas with bis-silylated amino acids polymeric products were obtained, which could not be characterized.

  DOI：

  10.1007/bf00808673
• 作为产物：
  描述：

  甘氨酸甲酯盐酸盐 、 六甲基二硅氮烷 在 三乙胺 作用下， 以 苯 为溶剂， 反应 2.0h， 以51%的产率得到Methyl [(trimethylsilyl)amino]acetate
  参考文献：
  名称：

  Organosilicon synthesis of isocyanates: III. Synthesis of aliphatic, carbocyclic, aromatic, and alkylaromatic isocyanatocatboxylic acid esters

  摘要：

  A series of aminoacid esters was prepared by treating the aminoacid suspensions in ethanol with thionyl chloride. Best conversion of aminoacid esters to corresponding isocyanates was achieved in the case of aromatic and carbocyclic aminoesters by phosgeneation of their N-silyl derivatives, and in the case of aliphatic and alkylaromatic aminoesters by phosgeneation of O-silyl or N,O-bissilylurethanes on their basis. In the last case additional step of esterification of the by-products isocyanatoalkylcarboxylic acid chlorides is reqired after phosgeneation. Unusual generation of cynnamates and intramolecular N -> O-migration of trimethylsilyl group in the solutions of silylated alkylaromatic beta-aminoacid esters were found.

  DOI：

  10.1134/s1070363206070115

文献信息

• Organosilicon synthesis of isocyanates: III. Synthesis of aliphatic, carbocyclic, aromatic, and alkylaromatic isocyanatocatboxylic acid esters
  作者：A. V. Lebedev、A. B. Lebedeva、V. D. Sheludyakov、S. N. Ovcharuk、E. A. Kovaleva、O. L. Ustinova

  DOI：10.1134/s1070363206070115

  日期：2006.7

  A series of aminoacid esters was prepared by treating the aminoacid suspensions in ethanol with thionyl chloride. Best conversion of aminoacid esters to corresponding isocyanates was achieved in the case of aromatic and carbocyclic aminoesters by phosgeneation of their N-silyl derivatives, and in the case of aliphatic and alkylaromatic aminoesters by phosgeneation of O-silyl or N,O-bissilylurethanes on their basis. In the last case additional step of esterification of the by-products isocyanatoalkylcarboxylic acid chlorides is reqired after phosgeneation. Unusual generation of cynnamates and intramolecular N -> O-migration of trimethylsilyl group in the solutions of silylated alkylaromatic beta-aminoacid esters were found.
• Fluordiazadiphosphetidine. 22. Mitt. Reaktionen von 2,2,2,4,4,4-Hexafluoro-1,3-dimethyl-1,3,2?5,4?5-diazadiphosphetidin mit silylierten Aminos�uren
  作者：M. Stepanovsky、A. Krill、K. Utvary

  DOI：10.1007/bf00808673

  日期：1993.2

  The interaction of silylated amino acids with hexafluorodiazadiphosphetidine was studied. With trimethlsilyl amino acid esters the substitution of one fluorine atom was accomplished, whereas with bis-silylated amino acids polymeric products were obtained, which could not be characterized.