(E)-5-methyltetrahydro-[2,3']-bifuranyliden-2'-one | 444327-05-3

• 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)-5-methyltetrahydro-[2,3']-bifuranyliden-2'-one
• 英文别名: (3E)-3-(5-methyloxolan-2-ylidene)oxolan-2-one
• CAS: 444327-05-3
• 化学式: C₉H₁₂O₃
• 分子量: 168.192
• InChiKey: UXJPBPWCVGACNA-BQYQJAHWSA-N

物化性质

• 沸点：
  301.4±31.0 °C(Predicted)
• 密度：
  1.210±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 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)-5-methyltetrahydro-[2,3']-bifuranyliden-2'-one 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48%的产率得到5-methyl-5'H-[2,3']bifuranyl-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：

  4-<1-(trimethylsiloxy)ethenyl>-5-(trimethylsiloxy)-2,3-dihydrofuran 、 methyloxirane 在 4 A molecular sieve 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以42%的产率得到(E)-5-methyltetrahydro-[2,3']-bifuranyliden-2'-one
  参考文献：
  名称：

  通过1,3-双（三甲基甲硅烷氧基）-1,3-丁二烯与环氧化物的环化反应合成官能化的2-亚烷基四氢呋喃。

  摘要：

  Lewis酸介导的1,3-双（三甲基甲硅烷氧基）-1,3-丁二烯，1,3-二羰基二价电子中性当量的环氧化物环化反应导致形成具有多种取代方式和功能的2-亚烷基四氢呋喃组。这包括2,3'-二呋喃基亚烷基和7-氧杂双环[4.3.0]壬烷的合成。二烯与含有碱不稳定基团的官能化环氧化物的环化反应具有良好的化学选择性。在所有反应中，均观察到良好的区域和E非对映选择性。基于观察到的1,2-二取代环氧化物反应的立体选择性，提出了反应机理的可行假设。

  DOI：

  10.1002/1521-3765(20020315)8:6<1443::aid-chem1443>3.0.co;2-0

文献信息

• Convenient Synthesis of ε-Halo-β-ketoesters and γ,γ‘-Dibromoalkanones by Regio- and Chemoselective Reaction of 2-Alkylidenetetrahydrofurans with Boron Trihalides: A “Ring-Closure/Ring-Cleavage” Strategy
  作者：Esen Bellur、Peter Langer

  DOI：10.1021/jo047824+

  日期：2005.5.1

  The reaction of boron tribromide and boron trichloride with 2-alkylidenetetrahydrofurans, readily available on the basis of cyclizations of free and masked dianions with 1,2-dielectrophiles, allowed an efficient synthesis of a variety of carbonyl compounds with remote halide functionality. This includes the chemo- and regioselective synthesis of 6-bromo- and 6-chloro-3-oxoalkanoates and 1,7-dibromoheptan-4-ones

  三溴化硼和三氯化硼与2-亚烷基四氢呋喃的反应很容易获得，该反应是基于游离的和掩蔽的二价阴离子与1,2-二亲电子试剂的环化而容易获得的，从而可以有效合成具有远程卤化物官能度的各种羰基化合物。这包括6-溴-3-和6-氯-3-氧代链烷酸酯和1,7-二溴庚烷-4-酮的化学和区域选择性合成。本文概述的方法可被视为“闭环/裂环”策略。
• 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.
• Synthesis of Functionalized 2-Alkylidenetetrahydrofurans by Cyclization of 1,3-Bis(trimethylsilyloxy)-1,3-butadienes with Epoxides
  作者：Peter Langer、Holger Armbrust、Tobias Eckardt、Jörg Magull

  DOI：10.1002/1521-3765(20020315)8:6<1443::aid-chem1443>3.0.co;2-0

  日期：2002.3.15

  7-oxabicyclo[4.3.0]nonanes. The cyclization of dienes with functionalized epoxides containing base-labile groups proceeds with good chemoselectivity. In all reactions, good regio- and E diastereoselectivities are observed. Based on the stereoselectivities observed for reactions of 1,2-disubstituted epoxides, a working hypothesis for the mechanism of the reaction is suggested.

  Lewis酸介导的1,3-双（三甲基甲硅烷氧基）-1,3-丁二烯，1,3-二羰基二价电子中性当量的环氧化物环化反应导致形成具有多种取代方式和功能的2-亚烷基四氢呋喃组。这包括2,3'-二呋喃基亚烷基和7-氧杂双环[4.3.0]壬烷的合成。二烯与含有碱不稳定基团的官能化环氧化物的环化反应具有良好的化学选择性。在所有反应中，均观察到良好的区域和E非对映选择性。基于观察到的1,2-二取代环氧化物反应的立体选择性，提出了反应机理的可行假设。