2-tert-butoxycarbamoyl-2-benzylmalonic acid allyl ester methyl ester | 242792-76-3

• 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: 2-tert-butoxycarbamoyl-2-benzylmalonic acid allyl ester methyl ester
• 英文别名: 1-O-methyl 3-O-prop-2-enyl 2-benzyl-2-[(2-methylpropan-2-yl)oxycarbamoyl]propanedioate
• CAS: 242792-76-3
• 化学式: C₁₉H₂₅NO₆
• 分子量: 363.411
• InChiKey: XUCDQADBBYXOCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  90.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-tert-butoxycarbamoyl-2-benzylmalonic acid allyl ester methyl ester 在 palladium diacetate 苯硅烷 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以98%的产率得到N-tert-butoxy-2-benzylmalonic acid methyl ester
  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
• 作为产物：
  描述：

  溴甲苯 、 2-tert-butoxycarbamoylmalonic acid allyl ester methyl ester 在 caesium carbonate 作用下， 以 丙酮 为溶剂， 反应 17.0h， 以72%的产率得到2-tert-butoxycarbamoyl-2-benzylmalonic acid allyl ester methyl ester
  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.