(E)-[dihydrofuran-2(3H)-ylidene]acetic acid isopropyl ester | 870693-39-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (E)-[dihydrofuran-2(3H)-ylidene]acetic acid isopropyl ester
• 英文别名: isopropyl (dihydrofuran-2(3H)-ylidene)acetate；(E)-isopropyl (dihydrofuran-2-ylidene)acetate；propan-2-yl (2E)-2-(oxolan-2-ylidene)acetate
• CAS: 870693-39-3
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: ZKYQOUXGQDLJMC-SOFGYWHQSA-N

物化性质

• 沸点：
  236.1±19.0 °C(Predicted)
• 密度：
  1.132±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• 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)-[dihydrofuran-2(3H)-ylidene]acetic acid isopropyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 48.0h， 以100%的产率得到iso-propyl (tetrahydrofuran-2-yl)acetate
  参考文献：
  名称：

  Synthesis of (tetrahydrofuran-2-yl)acetates based on a ‘cyclization/hydrogenation/enzymatic kinetic resolution’ strategy

  摘要：

  A variety of (tetrahydrofuran-2-yl)acetates and (pyrrolidin-2-yl)acetates have been prepared by hydrogenation of 2-alkylidene-tetrahydrofurans and 2-alkylidenepyrrolidines, which are readily available by cyclization reactions of 1,3-dicarbonyl dianions (free dianions') or 1,3-bis-silyl enol ethers ('masked dianions') with 1,2-dielectrophiles. The enzymatic kinetic resolution of (tetrahydrofuran-2-yl)acetates with recombinant esterase Est56 proceeded with excellent enantioselectivities (E > 100). (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.03.077
• 作为产物：
  描述：

  乙酰乙酸异丙酯 、 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 27.0h， 以64%的产率得到(E)-[dihydrofuran-2(3H)-ylidene]acetic acid isopropyl ester
  参考文献：
  名称：

  基于“[3+2]环化/溴化/消除”策略的功能化呋喃合成

  摘要：

  2-亚烷基四氢呋喃的溴化-通过一锅[3+2]环化很容易获得-得到2-亚烷基-3-溴四氢呋喃。溴化氢的消除和这些化合物的随后芳构化为官能化呋喃提供了一种方便的方法。

  DOI：

  10.1055/s-2006-926301

文献信息

• Synthesis of Functionalized 2-Alkylidene-tetrahydrofurans Based on a [3+2] Cyclization/Bromination/Palladium(0) Cross-Coupling Strategy
  作者：Esen Bellur、Peter Langer

  DOI：10.1002/ejoc.200500422

  日期：2005.11

  The bromination of 2-alkylidene-tetrahydrofurans and 2-alkylidene-pyrrolidines — readily available through one-pot [3+2] cyclization reactions — afforded 2-alkylidene-1′-bromotetrahydrofurans, 2-alkylidene-3-bromotetrahydrofurans and 2-alkylidene-1′,3-dibromotetrahydrofurans and their pyrrolidine counterparts. 2-Alkylidene-1′-bromotetrahydrofurans were functionalized by performing Suzuki and Heck reactions

  2-亚烷基-四氢呋喃和 2-亚烷基-吡咯烷的溴化——很容易通过一锅 [3+2] 环化反应获得——得到 2-亚烷基-1'-溴四氢呋喃、2-亚烷基-3-溴四氢呋喃和 2-亚烷基-1',3-二溴四氢呋喃及其吡咯烷对应物。2-Alkylidene-1'-bromotetrahydrofurans 通过进行 Suzuki 和 Heck 反应进行功能化。2-Alkylidene-1',3-dibromotetrahydrofurans 成功地用于新型双铃木反应。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• 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 Furans Based on a ‘[3+2] Cyclization/Bromination­/Elimination’ Strategy
  作者：Peter Langer、Esen Bellur

  DOI：10.1055/s-2006-926301

  日期：——

  The bromination of 2-alkylidenetetrahydrofurans -readily available via one-pot [3+2] cyclizations - afforded 2-alkylidene-3-bromotetrahydrofurans. Elimination of hydrogen bromide and subsequent aromatization of these compounds provided a convenient approach to functionalized furans.

  2-亚烷基四氢呋喃的溴化-通过一锅[3+2]环化很容易获得-得到2-亚烷基-3-溴四氢呋喃。溴化氢的消除和这些化合物的随后芳构化为官能化呋喃提供了一种方便的方法。
• Synthesis of (tetrahydrofuran-2-yl)acetates based on a ‘cyclization/hydrogenation/enzymatic kinetic resolution’ strategy
  作者：Esen Bellur、Ilia Freifeld、Dominique Böttcher、Uwe T. Bornscheuer、Peter Langer

  DOI：10.1016/j.tet.2006.03.077

  日期：2006.7

  A variety of (tetrahydrofuran-2-yl)acetates and (pyrrolidin-2-yl)acetates have been prepared by hydrogenation of 2-alkylidene-tetrahydrofurans and 2-alkylidenepyrrolidines, which are readily available by cyclization reactions of 1,3-dicarbonyl dianions (free dianions') or 1,3-bis-silyl enol ethers ('masked dianions') with 1,2-dielectrophiles. The enzymatic kinetic resolution of (tetrahydrofuran-2-yl)acetates with recombinant esterase Est56 proceeded with excellent enantioselectivities (E > 100). (c) 2006 Elsevier Ltd. All rights reserved.