N-tert-butoxycarbonyl-O-triethylsilyl-L-threonine N'-propargylamide | 803727-47-1

• 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-tert-butoxycarbonyl-O-triethylsilyl-L-threonine N'-propargylamide
• CAS: 803727-47-1
• 化学式: C₁₈H₃₄N₂O₄Si
• 分子量: 370.564
• InChiKey: BJCXHTPLQAIYAR-CABCVRRESA-N

物化性质

• 沸点：
  477.1±45.0 °C(Predicted)
• 密度：
  1.000±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.04
• 重原子数：
  25.0
• 可旋转键数：
  9.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  76.66
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  Boc-L-苏氨酸 在 N-甲基吗啉 、 咪唑 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-tert-butoxycarbonyl-O-triethylsilyl-L-threonine N'-propargylamide
  参考文献：
  名称：

  Synthesis and Properties of Serine- and Threonine-Based Helical Polyacetylenes

  摘要：

  Serine- and threonine-based acetylene monomers carrying hydroxyl group, N-tert-butoxycarbonyl-L-serine N'-propargylamide (1), N-tert-butoxycarbonyl-L-threoine N'-propargylamide (2), and their O-silylated monomers, N-tert-butoxycarbonyl-O-triethylslilyl-L-serine N'-propargylamide (3) and N-tertbutoxycarbonyl-O-triethylsilyl-L-threonine N'-propargylamide (4), were polymerized with a rhodium zwitterion catalyst in THF, MeOH, CH2Cl2, and toluene to afford the corresponding optically active poly(N-propargylamides) with moderate number-average molecular weights (4200-12 800) in good yields. The polymers exhibited large specific rotations (-172degrees to -955degrees) and clear CD signals at the absorption region of polyacetylene main chains. The CD signals of poly(1) and poly(2) appeared around 270-350 nm, while those of poly(3) and poly(4) appeared around 400 nm. It is considered that these polymers take helical structures with predominantly one-handed screw sense, whose helical pitches are different. The presence of intramolecular hydrogen bonding of poly(1) and poly(2) was confirmed by IR spectroscopy measured in CHCl3. Desilylation of poly(3) and poly(4) satisfactorily proceeded to afford the polymers exhibiting the same CD spectroscopic patterns as those of poly(1) and poly(2).

  DOI：

  10.1021/ma048391f