2-[4,5-dihydrofuran-2(3H)-ylidene]butyric acid ethyl ester | 286368-94-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 2-[4,5-dihydrofuran-2(3H)-ylidene]butyric acid ethyl ester
• 英文别名: (E)-2-[1-(ethoxycarbonyl)propylidene]tetrahydrofuran；ethyl 2-[dihydrofuran-2(3H)-ylidene]butyrate；ethyl (2E)-2-(oxolan-2-ylidene)butanoate
• CAS: 286368-94-3
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: KEHOJVSQEWQZJX-CMDGGOBGSA-N

物化性质

• 沸点：
  256.1±19.0 °C(Predicted)
• 密度：
  1.054±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• 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：

  2-[4,5-dihydrofuran-2(3H)-ylidene]butyric acid ethyl ester 在 四(三苯基膦)钯 potassium phosphate 、 N-溴代丁二酰亚胺(NBS) 作用下， 以 1,4-二氧六环 、 四氯化碳 为溶剂， 反应 9.0h， 生成 ethyl (E)-2-[3-(4-chlorophenyl)-4,5-dihydrofuran-2(3H)-ylidene]butyrate
  参考文献：
  名称：

  基于[3+2]环化/溴化/钯(0)交叉偶联策略合成功能化2-亚烷基-四氢呋喃

  摘要：

  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)

  DOI：

  10.1002/ejoc.200500422
• 作为产物：
  描述：

  1-溴-2-氯乙烷 、 2-乙基乙酰乙酸乙酯 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 27.0h， 生成 2-[4,5-dihydrofuran-2(3H)-ylidene]butyric acid ethyl 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

• 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.
• Langer, Peter; Karime, Inass, Synlett, 2000, # 5, p. 743 - 745
  作者：Langer, Peter、Karime, Inass

  DOI：——

  日期：——
• 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 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)