(S)-t-butyl 1-(5-formyl-oxazol-2-yl)-2-methyl-propylcarbamate | 1033037-46-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (S)-t-butyl 1-(5-formyl-oxazol-2-yl)-2-methyl-propylcarbamate
• 英文别名: tert-butyl N-[(1S)-1-(5-formyl-1,3-oxazol-2-yl)-2-methylpropyl]carbamate
• CAS: 1033037-46-5
• 化学式: C₁₃H₂₀N₂O₄
• 分子量: 268.313
• InChiKey: BQJJNVLLZACOAP-JTQLQIEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  81.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-(tert-butoxycarbonyl)-L-valine N'-propargylamide 在 双(乙腈)氯化钯(II) 氧气 、 copper dichloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以42%的产率得到(S)-t-butyl 1-(5-formyl-oxazol-2-yl)-2-methyl-propylcarbamate
  参考文献：
  名称：

  Intramolecular Pd(II)-Catalyzed Cyclization of Propargylamides: Straightforward Synthesis of 5-Oxazolecarbaldehydes

  摘要：

  Direct synthesis of 2-substituted 5-oxazolecarbaldehydes was performed by intramolecular reaction of propargylamides through treatment with a catalytic amount of Pd(II) salts in the presence of a stoichiometric amount of reoxidant agent. The heterocyclization process was well-tolerated by a wide range of aryl, heteroaryl, and alkyl propargylamides. This protocol constitutes a valuable synthetic pathway to 5-oxazolecarbaldehydes, alternative to the formylation on oxazole rings, often unsatisfactory in term of regioselectivity and yields.

  DOI：

  10.1021/jo800621n

文献信息

• Intramolecular Pd(II)-Catalyzed Cyclization of Propargylamides: Straightforward Synthesis of 5-Oxazolecarbaldehydes
  作者：Egle M. Beccalli、Elena Borsini、Gianluigi Broggini、Giovanni Palmisano、Silvia Sottocornola

  DOI：10.1021/jo800621n

  日期：2008.6.1

  Direct synthesis of 2-substituted 5-oxazolecarbaldehydes was performed by intramolecular reaction of propargylamides through treatment with a catalytic amount of Pd(II) salts in the presence of a stoichiometric amount of reoxidant agent. The heterocyclization process was well-tolerated by a wide range of aryl, heteroaryl, and alkyl propargylamides. This protocol constitutes a valuable synthetic pathway to 5-oxazolecarbaldehydes, alternative to the formylation on oxazole rings, often unsatisfactory in term of regioselectivity and yields.