N-tert-butoxycarbonyl-L-threonine N'-propargylamide | 803727-45-9

• 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-tert-butoxycarbonyl-L-threonine N'-propargylamide
• 英文别名: tert-butyl N-[(2S,3R)-3-hydroxy-1-oxo-1-(prop-2-ynylamino)butan-2-yl]carbamate
• CAS: 803727-45-9
• 化学式: C₁₂H₂₀N₂O₄
• 分子量: 256.302
• InChiKey: OEQOWMNKYJMYJF-BDAKNGLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-tert-butoxycarbonyl-L-threonine N'-propargylamide 、 methyl 2-(2-azido-2,2-difluoroacetamido)-3-phenylpropanoate 在 tris(benzyltriazolylmethyl)amine 、 copper(II) sulfate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 2.0h， 以82%的产率得到
  参考文献：
  名称：

  N-Difluoromethyl-triazole as a constrained scaffold in peptidomimetics

  摘要：

  核心肽中存在的N-二氟甲基三唑-β-氮杂-ε-氨基酸由于CH-F和NH-F的相互作用导致受限构象。

  DOI：

  10.1039/c7cc01298e
• 作为产物：
  描述：

  Boc-L-苏氨酸 、 炔丙胺 在 N-甲基吗啉 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 为溶剂， 以87%的产率得到N-tert-butoxycarbonyl-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

文献信息

• N-Difluoromethyl-triazole as a constrained scaffold in peptidomimetics
  作者：M. Mamone、R. S. B. Gonçalves、F. Blanchard、G. Bernadat、S. Ongeri、T. Milcent、B. Crousse

  DOI：10.1039/c7cc01298e

  日期：——

  The N-difluoromethyl triazolo-β-aza-ε-amino acid present in the core of peptides led to constrained conformations due to CH–F and NH–F interactions.

  核心肽中存在的N-二氟甲基三唑-β-氮杂-ε-氨基酸由于CH-F和NH-F的相互作用导致受限构象。
• Synthesis and Properties of Serine- and Threonine-Based Helical Polyacetylenes
  作者：Fumio Sanda、Hitoshi Araki、Toshio Masuda

  DOI：10.1021/ma048391f

  日期：2004.11.1

  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).