7-methylene-14-oxadispiro<4.0.5.3>tetradecan-13-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: 7-methylene-14-oxadispiro<4.0.5.3>tetradecan-13-one
• 英文别名: 1-Methylene-13-oxadispiro<5.0.5.3>pentadecan-14-one；12-Methylidene-15-oxadispiro[5.0.57.36]pentadecan-14-one
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: BATXUZSQWQMYES-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  二氧化碳 、 环己酮 、 1,2-bis(methylene)-cyclohexane-magnesium 在 oxonium 作用下， 生成 7-methylene-14-oxadispiro<4.0.5.3>tetradecan-13-one
  参考文献：
  名称：

  Synthesis of spiro .gamma.-lactones from conjugated dienes

  摘要：

  Stepwise reactions of conjugated dienemagnesium reagents with a ketone at -78-degrees-C, followed by carbon dioxide at 0-degrees-C to room temperature, provide a one-pot method for the synthesis of spiro gamma-lactones containing a vinyl group at the beta-position.

  DOI：

  10.1021/jo00052a004

文献信息

• Direct Synthesis of Spiro .delta.-lactones, Spiro-.gamma.-Lactones, and Alcohols from Substituted (2-Butene-1,4-diyl)magnesium Complexes
  作者：Reuben D. Rieke、Matthew S. Sell、Heping Xiong

  DOI：10.1021/jo00121a036

  日期：1995.8

  A convenient, one-pot process for the synthesis of spiro delta- and gamma-lactones and alcohols from conjugated dienes mediated by Rieke magnesium is described. This technique involves the treatment of a substituted (2-butene-1,4-diyl)magnesium complex with an epoxide or ketone at -78 degrees C, followed by the addition of carbon dioxide at 0 degrees C to room temperature. After acidic hydrolysis and subsequent warming, a spiro delta- or gamma-lactone accommodating both a quaternary carbon center and vinyl moiety at the beta-position is afforded in good isolated yield. Alternatively, acidic hydrolysis of the initially formed adduct at 0 degrees C furnishes an alcohol containing a quaternary carbon center in good to excellent chemical yield.
• Synthesis of spiro .gamma.-lactones from conjugated dienes
  作者：Heping Xiong、Reuben D. Rieke

  DOI：10.1021/jo00052a004

  日期：1992.12

  Stepwise reactions of conjugated dienemagnesium reagents with a ketone at -78-degrees-C, followed by carbon dioxide at 0-degrees-C to room temperature, provide a one-pot method for the synthesis of spiro gamma-lactones containing a vinyl group at the beta-position.