4-Ethyl-2,5,5-trimethyl-4,5-dihydrofuran-3-carboxylic acid ethyl ester

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 4-Ethyl-2,5,5-trimethyl-4,5-dihydrofuran-3-carboxylic acid ethyl ester
• 英文别名: ethyl 3-ethyl-2,2,5-trimethyl-3H-furan-4-carboxylate
• 化学式: C₁₂H₂₀O₃
• 分子量: 212.289
• InChiKey: VYKZPLDHFOBZSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  反-4-甲基-2-戊烯 、 乙酰乙酸乙酯 在 碘苯二乙酸 作用下， 以 乙腈 为溶剂， 反应 1.5h， 以43%的产率得到4-Ethyl-2,5,5-trimethyl-4,5-dihydrofuran-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Diacetoxyiodobenzene-mediated oxidative addition of 1,3-dicarbonyl compounds to olefins: an efficient one-pot synthesis of 2,3-dihydrofuran derivatives

  摘要：

  A variety of olefins react with -dicarbonyl compounds at 0degreesC in the presence of diacetoxyiodobenzene to afford highly substituted 2,3-dihydrofuran derivatives in good to excellent yields. (C) 2003 Published by Elsevier Ltd.

  DOI：

  10.1016/s0040-4039(03)01644-7

文献信息

• Oxidative addition of 1,3-dicarbonyl compounds to alkenes mediated by cerium(IV) ammonium nitrate and manganese(III) acetate: a comparative study
  作者：Vijay Nair、Jessy Mathew、K. V. Radhakrishnan

  DOI：10.1039/p19960001487

  日期：——

  The oxidative addition of dimedone, acetylacetone and ethyl acetoacetate to cyclic and acyclic alkenes mediated by CAN gives dihydrofurans in good yields. Similar addition of the radical generated from dimethyl malonate to alkenes provides lactones. A comparative study of these reactions vis-à-vis those mediated by Mn(OAc)3 has shown that the former generally lead to higher yields of products. The

  通过CAN介导，将二甲酮，乙酰丙酮和乙酰乙酸乙酯氧化加成到环状和无环烯烃中，可以得到高产率的二氢呋喃。由丙二酸二甲酯产生的自由基向烯烃的类似加成得到内酯。这些反应的比较研究可见- à -可见那些用Mn（OAC）介导的3表明，前者通常导致产品更高的产量。较温和的反应条件，简单的实验以及CAN在常见有机溶剂（如甲醇，乙腈和THF）中的溶解度是其他优势。因此，从这项研究看来，CAN优于常用的Mn（OAc）3。
• Diacetoxyiodobenzene-mediated oxidative addition of 1,3-dicarbonyl compounds to olefins: an efficient one-pot synthesis of 2,3-dihydrofuran derivatives
  作者：N.N Karade、S.G Shirodkar、M.N Patil、R.A Potrekar、H.N Karade

  DOI：10.1016/s0040-4039(03)01644-7

  日期：2003.8

  A variety of olefins react with -dicarbonyl compounds at 0degreesC in the presence of diacetoxyiodobenzene to afford highly substituted 2,3-dihydrofuran derivatives in good to excellent yields. (C) 2003 Published by Elsevier Ltd.