2-benzyl-N-(2-methylidenecyclopentyl)malonamic acid ethyl ester

• 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-benzyl-N-(2-methylidenecyclopentyl)malonamic acid ethyl ester
• 英文别名: Ethyl 2-benzyl-3-[(2-methylidenecyclopentyl)amino]-3-oxopropanoate
• 化学式: C₁₈H₂₃NO₃
• 分子量: 301.386
• InChiKey: HLQUBYMTJULFFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 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：

  2-苄基乙酰乙酸乙酯 在 三苯基膦 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 39.0h， 生成 2-benzyl-N-(2-methylidenecyclopentyl)malonamic acid ethyl ester
  参考文献：
  名称：

  Domino “Staudinger/Semi-Aza-Wittig/Fragmentation” Reactions of γ-Azido-β-hydroxyketones

  摘要：

  Treatment of gamma-azido-beta-hydroxyketones with triphenylphosphine resulted, depending on the structural features of the starting materials, in a domino "Staudinger/semi-aza-Wittig/fragmentation" reaction rather than a normal aza-Wittig reaction. 2-Azido-1-hydroxy-1-(2,4-dioxoalkyl)cyclopentanes, readily available by condensation of 1,3-dicarbonyl dianions with 2-azidocyclopentanone, proved to be optimal starting materials for these reactions which afforded 1-(1,3-dioxoalkyl)amino-2-(alkylidene)cyclopentanes.

  DOI：

  10.1021/jo060891e

文献信息

• Domino “Staudinger/Semi-Aza-Wittig/Fragmentation” Reactions of γ-Azido-β-hydroxyketones
  作者：Ilia Freifeld、Heydar Shojaei、Rüdiger Dede、Peter Langer

  DOI：10.1021/jo060891e

  日期：2006.8.1

  Treatment of gamma-azido-beta-hydroxyketones with triphenylphosphine resulted, depending on the structural features of the starting materials, in a domino "Staudinger/semi-aza-Wittig/fragmentation" reaction rather than a normal aza-Wittig reaction. 2-Azido-1-hydroxy-1-(2,4-dioxoalkyl)cyclopentanes, readily available by condensation of 1,3-dicarbonyl dianions with 2-azidocyclopentanone, proved to be optimal starting materials for these reactions which afforded 1-(1,3-dioxoalkyl)amino-2-(alkylidene)cyclopentanes.