(2E)-6,6-dimethyl-2-(2-methylpropylidene)-4,8-dioxaspiro[2.5]octane | 143682-00-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2E)-6,6-dimethyl-2-(2-methylpropylidene)-4,8-dioxaspiro[2.5]octane
• CAS: 143682-00-2
• 化学式: C₁₂H₂₀O₂
• 分子量: 196.29
• InChiKey: YAOHUEULTGOUTL-BJMVGYQFSA-N

物化性质

• 沸点：
  252.7±35.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  巴豆酸甲酯 、 (2E)-6,6-dimethyl-2-(2-methylpropylidene)-4,8-dioxaspiro[2.5]octane 在 溶剂黄146 作用下， 生成
  参考文献：
  名称：

  Regioselective and endo-stereoselective [3 + 2] cycloaddition of dipolar trimethylenemethane to electron-deficient olefin

  摘要：

  DOI：

  10.1021/ja00048a058
• 作为产物：
  描述：

  6,6-二甲基-4,8-二氧杂螺[2.5]辛-1-烯 在 正丁基锂 、 potassium tert-butylate 作用下， 以 乙醚 、 二甲基亚砜 为溶剂， 反应 1.58h， 生成 (2E)-6,6-dimethyl-2-(2-methylpropylidene)-4,8-dioxaspiro[2.5]octane
  参考文献：
  名称：

  Thermal Hetero [3 + 2] Cycloaddition of Dipolar Trimethylenemethane to O-Alkyloximes. Straightforward Synthetic Routes to Substituted Pyrrolidines and Prolines

  摘要：

  Thermal hetero [3 + 2] cycloaddition reaction of a dipolar trimethylenemethane 2 with an O-alkyloxime produces a substituted pyrrolidine. Thus, heating of a mixture of an alkylidenecyclopropane 1 an anti-O-alkyloxime 3 proceeds smoothly in good yield to give a substituted pyrrolidine 4 bearing a ketene acetal group in its 3-position, which upon hydrolysis under mild conditions gives a 3-alkoxycarbonylpyrrolidne 5 in quantitative yield. On the other hand, the cycloaddition to a syn-oxime is extremely slow. The cycloaddition reaction can be achieved by starting with nearly equimolar quantities of the two starting materials, and the reaction is quite insensitive to the choice of solvent and to the presence of oxygen and water. In the reaction of a substituted methylenecyclopropane 1 (R not equal H), the reaction may take place with high regio-and stereoselectivity, which is in consonance with the concerted nature of the cycloaddition reaction. The present synthesis represents one of the rare examples of the imine-based route to pyrrolidines, which have been much less explored than the 1,3-dipolar cycloaddition route using olefin and azomethine ylide.

  DOI：

  10.1021/jo972302y