methyl 4-cyano-4-((ethoxycarbonyl)oxy)-2-methylene-6-phenylhexanoate | 1373932-53-6

• 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: methyl 4-cyano-4-((ethoxycarbonyl)oxy)-2-methylene-6-phenylhexanoate
• CAS: 1373932-53-6
• 化学式: C₁₈H₂₁NO₅
• 分子量: 331.368
• InChiKey: JUMWYFUBOPGOCZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.17
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  85.62
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 4-cyano-4-((ethoxycarbonyl)oxy)-2-methylene-6-phenylhexanoate 在 二乙基苯膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以91%的产率得到1-ethyl 3-methyl 2-(cyanomethyl)-2-(2-oxo-4-phenylbutyl)malonate
  参考文献：
  名称：

  Lewis Base Promoted Intramolecular Acylcyanation of α-Substituted Activated Alkenes: Construction of Ketones Bearing β-Quaternary Carbon Centers

  摘要：

  A novel phosphine-promoted intramolecular acylcyanation of alpha-substituted activated alkenes has been developed, which provides a unique access to densely functionalized acyclic ketones bearing beta-quaternary carbon centers with a remarkable feature that both alpha- and beta-positions of activated alkene are functionalized.

  DOI：

  10.1021/ol3007716
• 作为产物：
  描述：

  2-(溴甲基)丙烯酸甲酯 、 carbonic acid, 1-cyano-3-phenylpropyl ethyl ester 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以27%的产率得到methyl 4-cyano-4-((ethoxycarbonyl)oxy)-2-methylene-6-phenylhexanoate
  参考文献：
  名称：

  Lewis Base Promoted Intramolecular Acylcyanation of α-Substituted Activated Alkenes: Construction of Ketones Bearing β-Quaternary Carbon Centers

  摘要：

  A novel phosphine-promoted intramolecular acylcyanation of alpha-substituted activated alkenes has been developed, which provides a unique access to densely functionalized acyclic ketones bearing beta-quaternary carbon centers with a remarkable feature that both alpha- and beta-positions of activated alkene are functionalized.

  DOI：

  10.1021/ol3007716