tert-butyl N-[furan-2-yl(trimethylsilyl)methyl]carbamate | 847180-69-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: tert-butyl N-[furan-2-yl(trimethylsilyl)methyl]carbamate
• CAS: 847180-69-2
• 化学式: C₁₃H₂₃NO₃Si
• 分子量: 269.416
• InChiKey: ZNFSOGYNZNDKEQ-UHFFFAOYSA-N

物化性质

• 熔点：
  57-58 °C
• 沸点：
  316.6±37.0 °C(Predicted)
• 密度：
  0.999±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.72
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  51.47
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[furan-2-yl(trimethylsilyl)methyl]carbamate 在 臭氧 作用下， 生成 2-[(2-methylpropan-2-yl)oxycarbonylamino]-2-trimethylsilylacetic acid
  参考文献：
  名称：

  α-Trialkylsilyl Amino Acid Stability

  摘要：

  alpha-Trialkylsilyl amino acids have been evaluated for their stability toward methanolysis as a model for physiological conditions. The juxtaposition of amine and carbonyl groups significantly destabilizes the silicon-carbon bond, but changing a single methyl on silicon to an ethyl led to a dramatic stability enhancement. Converting the ester to an amide gave an additional jump in stability, suggesting broad potential for these novel amino acids in bioactive peptides and pharmaceuticals.

  DOI：

  10.1021/ol047508h
• 作为产物：
  描述：

  三甲基氯硅烷 、 2-甲基-2-丙基(2-呋喃甲基)氨基甲酸酯 在 正丁基锂 作用下， 以80%的产率得到tert-butyl N-[furan-2-yl(trimethylsilyl)methyl]carbamate
  参考文献：
  名称：

  α-Trialkylsilyl Amino Acid Stability

  摘要：

  alpha-Trialkylsilyl amino acids have been evaluated for their stability toward methanolysis as a model for physiological conditions. The juxtaposition of amine and carbonyl groups significantly destabilizes the silicon-carbon bond, but changing a single methyl on silicon to an ethyl led to a dramatic stability enhancement. Converting the ester to an amide gave an additional jump in stability, suggesting broad potential for these novel amino acids in bioactive peptides and pharmaceuticals.

  DOI：

  10.1021/ol047508h