N-trimethylsilylhomovaline ethyl ester | 945419-99-8

• 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-trimethylsilylhomovaline ethyl ester
• CAS: 945419-99-8
• 化学式: C₁₁H₂₅NO₂Si
• 分子量: 231.41
• InChiKey: CTQLNTCEWJHCNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.39
• 重原子数：
  15.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  38.33
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  光气 、 N-trimethylsilylhomovaline ethyl ester 以 甲苯 为溶剂， 以58%的产率得到ethyl 3-isocyanato-4-methylpentanoate
  参考文献：
  名称：

  Organosilicon synthesis of isocyanates: IV. Synthesis of isocyanates from aliphatic and alkylaromatic amino acid esters

  摘要：

  Treatment of an alcoholic suspension of amino acids with trimethylchlorosilane yielded phenylglycine, valine, beta-phenylalanine, and homovaline ester hydrochlorides. Their saccharin-catalyzed silylation with hexamethyldisilazane proceeds quantitatively and involves only one proton of the amino group. The best conversion of the amino acid esters to the corresponding isocyanates was achieved by phosgene treatment of their monosilyl urethanes, rather than of the silylated amino esters. Monosilyl urethanes are formed quantitatively by treatment of the amino acid ester hydrochlorides with the hexamethyldisilazane-CO2 system. The H-1 NMR spectra show that monosilyl urethanes derived from alpha- and beta-amino acid esters are characterized by intramolecular interaction of the silicon atom and the oxygen atom of the carboxy group.

  DOI：

  10.1134/s1070363207040135
• 作为产物：
  描述：

  3-氨基-4-甲基戊酸 在 三甲基氯硅烷 、 三乙胺 、 糖精 作用下， 以 甲苯 为溶剂， 生成 N-trimethylsilylhomovaline ethyl ester
  参考文献：
  名称：

  Organosilicon synthesis of isocyanates: IV. Synthesis of isocyanates from aliphatic and alkylaromatic amino acid esters

  摘要：

  Treatment of an alcoholic suspension of amino acids with trimethylchlorosilane yielded phenylglycine, valine, beta-phenylalanine, and homovaline ester hydrochlorides. Their saccharin-catalyzed silylation with hexamethyldisilazane proceeds quantitatively and involves only one proton of the amino group. The best conversion of the amino acid esters to the corresponding isocyanates was achieved by phosgene treatment of their monosilyl urethanes, rather than of the silylated amino esters. Monosilyl urethanes are formed quantitatively by treatment of the amino acid ester hydrochlorides with the hexamethyldisilazane-CO2 system. The H-1 NMR spectra show that monosilyl urethanes derived from alpha- and beta-amino acid esters are characterized by intramolecular interaction of the silicon atom and the oxygen atom of the carboxy group.

  DOI：

  10.1134/s1070363207040135

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.