(2E)-二氢-2(3H)-呋喃亚基乙酸乙酯 | 99054-37-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 中文名称: (2E)-二氢-2(3H)-呋喃亚基乙酸乙酯
• 英文名称: ethyl (E)-(2-tetrahydrofuranylidene)acetate
• 英文别名: (E)-2-(ethoxycarbonylmethylidene)tetrahydrofuran；Aethyl α-(tetrahydro-2-furyliden)-acetat；α-(Tetrahydro-2-furyliden)essigsaeureethylester；Ethyl E-(dihydrofuran-2-ylidene)acetate；ethyl (2E)-2-(oxolan-2-ylidene)acetate
• CAS: 99054-37-2
• 化学式: C₈H₁₂O₃
• 分子量: 156.181
• InChiKey: FWALKMNFOWCSQI-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2932190090

反应信息

• 作为反应物：
  描述：

  (2E)-二氢-2(3H)-呋喃亚基乙酸乙酯 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 四氯化碳 为溶剂， 反应 3.0h， 以93%的产率得到Bromo-[3-bromo-dihydro-furan-(2Z)-ylidene]-acetic acid ethyl ester
  参考文献：
  名称：

  Functionalization of 2-Alkylidenetetrahydrofurans and 2-Alkylidene­pyrrolidines by Palladium(0)-Catalyzed Cross-Coupling Reactions

  摘要：

  通过环外双键的溴化和随后的钯催化的交叉偶联反应，2-亚烷基四氢呋喃和2-亚烷基吡咯烷被有效地官能化。

  DOI：

  10.1055/s-2004-830892
• 作为产物：
  描述：

  ethyl 6-hydroxyhex-2-ynoate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以86%的产率得到(2E)-二氢-2(3H)-呋喃亚基乙酸乙酯
  参考文献：
  名称：

  TBAF-catalyzed cyclization of 6-hydroxyhex-2-ynoates and 7-hydroxyhept-2-ynoates

  摘要：

  Tetrabutyl ammonium fluoride (TBAF) was found to be capable of catalyzing the intramolecular hydroalkoxylation of 6-hydroxyhex-2-ynoates and 7-hydroxyhept-2-ynoates. The reaction could be used to prepare 2,5-substituted THF rings and 2,6-substituted THP rings. (C) 2011 Wei Yu. Published by Elsevier BY, on behalf of Chinese Chemical Society. All rights reserved.

  DOI：

  10.1016/j.cclet.2011.01.023

文献信息

• Synthesis of Benzofurans with Remote Bromide Functionality by Domino “Ring-Cleavage-Deprotection-Cyclization” Reactions of 2-Alkylidenetetrahydrofurans with Boron Tribromide
  作者：Esen Bellur、Peter Langer

  DOI：10.1021/jo051079z

  日期：2005.9.1

  Bromination and subsequent Suzuki reactions of 2-alkylidenetetrahydrofurans, readily available by [3+2] cyclizations, afforded 1‘-(2‘ ‘-methoxyphenyl)-2-alkylidenetetrahydrofurans. Treatment of the latter with boron tribromide and subsequent addition of water resulted in the chemoselective formation of functionalized benzofurans containing a remote bromide functionality. The products are formed by

  通过[3 + 2]环化容易获得的2-亚烷基四氢呋喃的溴化反应和随后的Suzuki反应，得到1'-（2''-甲氧基苯基）-2-亚烷基四氢呋喃。用三溴化硼处理后者并随后加水导致化学选择性地形成官能化的苯并呋喃，该苯并呋喃具有较远的溴化物官能度。产品是通过新的多米诺骨牌“环断裂-去保护-环化”反应形成的。通过“环裂解-脱保护-环-封闭-内酯化”反应，加入叔丁醇钾的水溶液而不是水，得到了茶氨酸的饱和类似物。
• Chemoselective, Regioselective, and <i>E</i>/<i>Z</i>-Diastereoselective Synthesis of 2-Alkylidenetetrahydrofurans by Sequential Reactions of Ambident Dianions and Monoanions
  作者：Peter Langer、Esen Bellur

  DOI：10.1021/jo034966f

  日期：2003.12.1

  A number of novel beta-ketoesters were prepared by regioselective alkylation reactions of simple beta-ketoester dianions. The cyclization of the dianions of these 1,3-dicarbonyl derivatives with 1-bromo-2-chloroethane afforded a variety of 2-alkylidenetetrahydrofurans with very good regioselectivity and E/Z-diastereoselectivity. These products were deprotonated to give novel ambident carbanions. The

  通过简单的β-酮酯二价基团的区域选择性烷基化反应制备了许多新颖的β-酮酯。这些1-，3-二羰基衍生物的二价阴离子与1-溴-2-氯乙烷的环化反应提供了具有非常好的区域选择性和E / Z-非对映选择性的各种2-亚烷基四氢呋喃。这些产品被去质子化，以产生新颖的碳负离子。这些碳负离子用卤代烷进行的烷基化反应具有非常好的区域选择性和E / Z-非对映选择性，并可以方便地合成许多新的2-亚烷基四氢呋喃。
• 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)
• 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。
• Reaction of 2-Alkylidenetetrahydrofurans with Boron Tribromide: Chemo- and Regioselective Synthesis of 6-Bromo-3-oxoalkanoates by ­Application of a ‘Cyclization-Ring-Opening’ Strategy
  作者：Peter Langer、Esen Bellur

  DOI：10.1055/s-2004-830893

  日期：——

  Bromo-3-oxoalkanoates, benzofurans and 1,7-dibro- moheptan-4-ones were chemo- and regioselectively prepared by reaction of 2-alkylidenetetrahydrofurans with boron tribromide.

  Bromo-3-oxoalkanoates、benzofurans 和 1,7-dibro-heptan-4-ones 是通过 2-亚烷基四氢呋喃与三溴化硼反应的化学和区域选择性制备的。

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