(E)-2-(5-ethyl-2-oxotetrahydrofuran-3-ylidene)tetrahydrofuran

• 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: (E)-2-(5-ethyl-2-oxotetrahydrofuran-3-ylidene)tetrahydrofuran
• 英文别名: (3E)-5-ethyl-3-(oxolan-2-ylidene)oxolan-2-one
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: OLQPLJNCZMLHTG-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (E)-2-(5-ethyl-2-oxotetrahydrofuran-3-ylidene)tetrahydrofuran 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 为溶剂， 反应 48.0h， 以42%的产率得到5-ethyl-3-(2-furyl)-2,5-dihydrofuran-2-one
  参考文献：
  名称：

  Efficient Synthesis of Furan-2-ylacetates, 7-(Alkoxycarbonyl)benzofurans, and 7-(Alkoxycarbonyl)-2,3-dihydrobenzofurans Based on Cyclization Reactions of Free and Masked Dianions:  A “Cyclization/Dehydrogenation” Strategy

  摘要：

  A variety of furan-2-ylacetates have been prepared by dehydrogenation of monocyclic 2-alkylidene-tetrahydrofurans, which are readily available by cyclizations of open-chained 1,3-dicarbonyl dianions with 1-bromo-2-chloroethane. 5'H-[2,3']Bifuranyl-2'-ones are available based on sequential "cyclization/dehydrogenation" reactions of alpha-acetyl-gamma-butyrolactones. A variety of 7-(alkoxycarbonyl)-benzofarans and 7-(alkoxycarbonyl)-2,3-dihydrobenzofurans were prepared by a cyclization/ dehydrogenation strategy. These reactions rely on cyclizations of 2-oxocycloalkane-1-carboxylate/derived 1,3-dicarbonyl dianions ("free dianions") or 1,3-bis-silyl enol ethers ("masked dianions") with various 1,2-dielectrophiles.

  DOI：

  10.1021/jo051767i
• 作为产物：
  描述：

  3-acetyl-5-ethyldihydro-2(3H)-furanone 、 1-溴-2-氯乙烷 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 28.75h， 以62%的产率得到(E)-2-(5-ethyl-2-oxotetrahydrofuran-3-ylidene)tetrahydrofuran
  参考文献：
  名称：

  Regio- and Diastereoselective Synthesis of 2-Alkylidenetetrahydrofurans by Domino S_N/S_N‘ and S_N/S_N Reactions of 1,3-Dicarbonyl Dianions

  摘要：

  The domino C,O-cyclodialkylation reaction of dilithiated 1,3.-dicarbonyl compounds with 1,4-dibromo-2-butene resulted in regio- and diastereoselective formation of 2-alkylidene-5-vinyltetrahydrofurans. The cyclization of 1,3-dicarbonyl dianions with 1-bromo-2-chloroethane regio- and diastereoselectively afforded 2-alkylidenetetrahydrofurans under thermodynamic reaction control.

  DOI：

  10.1021/jo010303r

文献信息

• Efficient Synthesis of Furan-2-ylacetates, 7-(Alkoxycarbonyl)benzofurans, and 7-(Alkoxycarbonyl)-2,3-dihydrobenzofurans Based on Cyclization Reactions of Free and Masked Dianions:  A “Cyclization/Dehydrogenation” Strategy
  作者：Esen Bellur、Peter Langer

  DOI：10.1021/jo051767i

  日期：2005.11.1

  A variety of furan-2-ylacetates have been prepared by dehydrogenation of monocyclic 2-alkylidene-tetrahydrofurans, which are readily available by cyclizations of open-chained 1,3-dicarbonyl dianions with 1-bromo-2-chloroethane. 5'H-[2,3']Bifuranyl-2'-ones are available based on sequential "cyclization/dehydrogenation" reactions of alpha-acetyl-gamma-butyrolactones. A variety of 7-(alkoxycarbonyl)-benzofarans and 7-(alkoxycarbonyl)-2,3-dihydrobenzofurans were prepared by a cyclization/ dehydrogenation strategy. These reactions rely on cyclizations of 2-oxocycloalkane-1-carboxylate/derived 1,3-dicarbonyl dianions ("free dianions") or 1,3-bis-silyl enol ethers ("masked dianions") with various 1,2-dielectrophiles.
• Regio- and Diastereoselective Synthesis of 2-Alkylidenetetrahydrofurans by Domino S_N/S_N‘ and S_N/S_N Reactions of 1,3-Dicarbonyl Dianions
  作者：Peter Langer、Edith Holtz、Inass Karimé、Nehad N. R. Saleh

  DOI：10.1021/jo010303r

  日期：2001.9.1

  The domino C,O-cyclodialkylation reaction of dilithiated 1,3.-dicarbonyl compounds with 1,4-dibromo-2-butene resulted in regio- and diastereoselective formation of 2-alkylidene-5-vinyltetrahydrofurans. The cyclization of 1,3-dicarbonyl dianions with 1-bromo-2-chloroethane regio- and diastereoselectively afforded 2-alkylidenetetrahydrofurans under thermodynamic reaction control.