ethyl (E)-2-[5-vinyl-4,5-dihydrofuran-2(3H)-ylidene]acetate | 307317-69-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢呋喃
• 英文名称: ethyl (E)-2-[5-vinyl-4,5-dihydrofuran-2(3H)-ylidene]acetate
• 英文别名: ethyl (5-vinyldihydrofuran-2(3H)-ylidene)acetate；ethyl (2E)-2-(5-ethenyloxolan-2-ylidene)acetate
• CAS: 307317-69-7
• 化学式: C₁₀H₁₄O₃
• 分子量: 182.219
• InChiKey: MRRLZRIKVYWJNH-VQHVLOKHSA-N

物化性质

• 沸点：
  248.5±40.0 °C(Predicted)
• 密度：
  1.180±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  ethyl (E)-2-[5-vinyl-4,5-dihydrofuran-2(3H)-ylidene]acetate 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到8-bromo-3-oxooct-6-enoic acid ethyl ester
  参考文献：
  名称：

  通过2-亚烷基四氢呋喃与三卤化硼的区域和化学选择反应方便地合成ε-卤代-β-酮酸酯和γ，γ'-二溴代链烷酮：“环-封闭/环-裂解”策略

  摘要：

  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。

  DOI：

  10.1021/jo047824+
• 作为产物：
  描述：

  ethyl 6-hydroxyoct-7-en-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64%的产率得到ethyl (E)-2-[5-vinyl-4,5-dihydrofuran-2(3H)-ylidene]acetate
  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 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)
• Stereoselective Synthesis and Palladium-Catalyzed Transformations of 2-Alkylidene- 5-vinyltetrahydrofurans
  作者：Peter Langer、Edith Holtz

  DOI：10.1002/1521-3773(20000901)39:17<3086::aid-anie3086>3.0.co;2-f

  日期：2000.9.1
• Enantioselective synthesis of 2-alkylidenetetrahydrofurans based on a ‘cyclization/enzymatic resolution’ strategy
  作者：Esen Bellur、Dominique Böttcher、Uwe Bornscheuer、Peter Langer

  DOI：10.1016/j.tetasy.2006.03.006

  日期：2006.3

  Enantionterically pure 2-alkylidenetetrahydrofurans have been prepared by TiCl4 mediated enantiospecific reactions of 1,3-bis-silyl enol ethers with enantiomerically pure epichlorohydrin. In addition, the enzymatic kinetic resolution of 2-alkylidenetetrahydrofurans, using Candida antarctica lipase B (CAL-B), was studied. Enzymatic kinetic resolution of monocyclic 5-vinyl-2-alkylidenetetrahydrofuran with CAL-B afforded the enantiomerically pure ester with 97% ee. For a bicyclic 2-alkylidenetetrahydrofuran, this proceeded with excellent enantioselectivity (E > 100) affording the enantiomerically pure acid with 98% ee. 2-Alkylidenetetrahydrofurans were prepared by [3+2] cyclization reactions of 1,3-dicarbonyl dianions ('free dianions') or 1,3-bis-silyl enol ethers ('masked dianions'). (c) 2006 Published by Elsevier Ltd.
• TBAF-catalyzed cyclization of 6-hydroxyhex-2-ynoates and 7-hydroxyhept-2-ynoates
  作者：Xiao Qing Wang、Ping Jing Jia、Su Ping Liu、Wei Yu

  DOI：10.1016/j.cclet.2011.01.023

  日期：2011.8

  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.
• 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。