methyl 2-((1, 3-dioxolan-2-yl)methyl)-4-(4-(tert-butyl)phenyl)-4-oxobutanoate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-((1, 3-dioxolan-2-yl)methyl)-4-(4-(tert-butyl)phenyl)-4-oxobutanoate
• 英文别名: Methyl 4-(4-tert-butylphenyl)-2-(1,3-dioxolan-2-ylmethyl)-4-oxobutanoate；methyl 4-(4-tert-butylphenyl)-2-(1,3-dioxolan-2-ylmethyl)-4-oxobutanoate
• 化学式: C₁₉H₂₆O₅
• 分子量: 334.412
• InChiKey: BEGMWWZJSAUKQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2-((1, 3-dioxolan-2-yl)methyl)-4-(4-(tert-butyl)phenyl)-4-oxobutanoate 在 对甲苯磺酸 、 盐酸 作用下， 以 甲醇 、 四氢呋喃 为溶剂， 反应 10.0h， 以95%的产率得到methyl 4-(4-(tert-butyl)phenyl)-4-oxo-2-(2-oxoethyl)butanoate
  参考文献：
  名称：

  Radical–Polar Crossover Reactions: Oxidative Coupling of 1,3-Dioxolanes with Electron-Deficient Alkenes and Vinylarenes Based on a Radical Addition and Kornblum–DeLaMare Rearrangement

  摘要：

  A new radical-polar crossover reaction has been developed involving the combination of a tandem radical reaction and KornblumDeLaMare rearrangement in a one-pot process. This simple methodology allows for the construction of polyfunctionalized carbonyl compounds via the oxidative coupling of 1,3-dioxolanes with electron-deficient alkenes and vinylarenes in the presence of Co(salen) and TBHP under mild conditions. This reaction also exhibited high functional group tolerance, wide substrate scope, and operational simplicity.

  DOI：

  10.1021/ol503128j
• 作为产物：
  描述：

  4-叔丁基苯乙烯 在 salcomine 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙腈 为溶剂， 反应 1.5h， 生成 methyl 2-((1, 3-dioxolan-2-yl)methyl)-4-(4-(tert-butyl)phenyl)-4-oxobutanoate
  参考文献：
  名称：

  Radical–Polar Crossover Reactions: Oxidative Coupling of 1,3-Dioxolanes with Electron-Deficient Alkenes and Vinylarenes Based on a Radical Addition and Kornblum–DeLaMare Rearrangement

  摘要：

  A new radical-polar crossover reaction has been developed involving the combination of a tandem radical reaction and KornblumDeLaMare rearrangement in a one-pot process. This simple methodology allows for the construction of polyfunctionalized carbonyl compounds via the oxidative coupling of 1,3-dioxolanes with electron-deficient alkenes and vinylarenes in the presence of Co(salen) and TBHP under mild conditions. This reaction also exhibited high functional group tolerance, wide substrate scope, and operational simplicity.

  DOI：

  10.1021/ol503128j

文献信息

• Radical–Polar Crossover Reactions: Oxidative Coupling of 1,3-Dioxolanes with Electron-Deficient Alkenes and Vinylarenes Based on a Radical Addition and Kornblum–DeLaMare Rearrangement
  作者：Peng Du、Huihuang Li、Yaxiong Wang、Jiang Cheng、Xiaobing Wan

  DOI：10.1021/ol503128j

  日期：2014.12.19

  A new radical-polar crossover reaction has been developed involving the combination of a tandem radical reaction and KornblumDeLaMare rearrangement in a one-pot process. This simple methodology allows for the construction of polyfunctionalized carbonyl compounds via the oxidative coupling of 1,3-dioxolanes with electron-deficient alkenes and vinylarenes in the presence of Co(salen) and TBHP under mild conditions. This reaction also exhibited high functional group tolerance, wide substrate scope, and operational simplicity.