N-trimethylsilylhomovaline trimethylsilyl ester | 58521-57-6

• 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: N-trimethylsilylhomovaline trimethylsilyl ester
• CAS: 58521-57-6
• 化学式: C₁₂H₂₉NO₂Si₂
• 分子量: 275.539
• InChiKey: LRESVMBHXFPGSB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17.0
• 可旋转键数：
  6.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 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 trimethylsilyl ester 以 甲苯 为溶剂， 以41%的产率得到3-isocyanato-4-methylpentanoyl chloride
  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：

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

  Birkofer,L.; Schramm,J., Justus Liebigs Annalen der Chemie, 1975, p. 2195 - 2200

  摘要：

  DOI：

文献信息

• Birkofer,L.; Schramm,J., Justus Liebigs Annalen der Chemie, 1975, p. 2195 - 2200
  作者：Birkofer,L.、Schramm,J.

  DOI：——

  日期：——
• Organosilicon synthesis of isocyanates: IV. Synthesis of isocyanates from aliphatic and alkylaromatic amino acid esters
  作者：A. V. Lebedev、A. B. Lebedeva、V. D. Sheludyakov、V. V. Shatunov、S. N. Ovcharuk

  DOI：10.1134/s1070363207040135

  日期：2007.4

  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.