6-butyltetrahydro-4-methyl-4-(1-methylethenyl)-2H-pyran-2-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: 6-butyltetrahydro-4-methyl-4-(1-methylethenyl)-2H-pyran-2-one
• 英文别名: 6-Butyl-4-methyl-4-prop-1-en-2-yloxan-2-one
• 化学式: C₁₃H₂₂O₂
• 分子量: 210.316
• InChiKey: SOAHGVQIXXCZFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 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：

  丁基环氧乙烷 在 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 1.83h， 生成 6-butyltetrahydro-4-methyl-4-(1-methylethenyl)-2H-pyran-2-one
  参考文献：
  名称：

  Direct synthesis of spiro δ-lactones from conjugated dienes and epoxides

  摘要：

  Stepwise reactions of conjugated diene-magnesium reagents with an epoxide followed by carbon dioxide provide a direct method for a one-pot synthesis of spiro delta-lactones accommodating a vinyl moiety at the beta-position.

  DOI：

  10.1016/s0040-4039(00)61713-6

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.
• Direct synthesis of spiro δ-lactones from conjugated dienes and epoxides
  作者：Matthew S. Sell、Heping Xiong、Reuben D. Rieke

  DOI：10.1016/s0040-4039(00)61713-6

  日期：1993.9

  Stepwise reactions of conjugated diene-magnesium reagents with an epoxide followed by carbon dioxide provide a direct method for a one-pot synthesis of spiro delta-lactones accommodating a vinyl moiety at the beta-position.