2-oxocyclopentanecarboxylic acid tert-butoxyamide

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-oxocyclopentanecarboxylic acid tert-butoxyamide
• 英文别名: N-[(2-methylpropan-2-yl)oxy]-2-oxocyclopentane-1-carboxamide
• 化学式: C₁₀H₁₇NO₃
• 分子量: 199.25
• InChiKey: LYSWRWSGLMYZJB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-tert-butoxycarbamoyl-2-oxocyclopentanecarboxylic acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以61%的产率得到2-oxocyclopentanecarboxylic acid tert-butoxyamide
  参考文献：
  名称：

  Synthesis of Hydroxamic Esters via Alkoxyaminocarbonylation of β-Dicarbonyl Compounds

  摘要：

  N-t-Butoxycarbonyl-O-sulfonyl-substitute hydroxylamines react with soft enolates to yield O-t-butoxycarbonylamino derivatives rather than the expected Boc-protected amino acids. The reaction is limited to enolates of beta-dicarbonyl compounds. Decarboxylation of the resultant tricarbonyl compound affords malonyl alpha-alkyl O-t-butoxycarbonylamino derivatives.

  DOI：

  10.1021/jo990353k

文献信息

• Synthesis of Hydroxamic Esters via Alkoxyaminocarbonylation of β-Dicarbonyl Compounds
  作者：Stephen Hanessian、Shawn Johnstone

  DOI：10.1021/jo990353k

  日期：1999.8.1

  N-t-Butoxycarbonyl-O-sulfonyl-substitute hydroxylamines react with soft enolates to yield O-t-butoxycarbonylamino derivatives rather than the expected Boc-protected amino acids. The reaction is limited to enolates of beta-dicarbonyl compounds. Decarboxylation of the resultant tricarbonyl compound affords malonyl alpha-alkyl O-t-butoxycarbonylamino derivatives.