2-(E)-(ethoxycarbonylmethylidene)-5-ethyltetrahydrofuran | 40954-16-3

• 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: 2-(E)-(ethoxycarbonylmethylidene)-5-ethyltetrahydrofuran
• 英文别名: Aethyl α-(tetrahydro-5-aethyl-2-furyliden)-acetat；ethyl (2E)-2-(5-ethyloxolan-2-ylidene)acetate
• CAS: 40954-16-3
• 化学式: C₁₀H₁₆O₃
• 分子量: 184.235
• InChiKey: ORMZEGHFMGIRLM-VQHVLOKHSA-N

物化性质

• 沸点：
  253.4±19.0 °C(Predicted)
• 密度：
  1.077±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 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-(E)-(ethoxycarbonylmethylidene)-5-ethyltetrahydrofuran 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.5h， 生成 ethyl (5-ethyltetrahydrofuran-2-yl)acetate 、 ethyl (5-ethyltetrahydrofuran-2-yl)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
• 作为产物：
  描述：

  C₁₀H₁₆O₃ 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以65%的产率得到2-(E)-(ethoxycarbonylmethylidene)-5-ethyltetrahydrofuran
  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-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。
• Chemo-, Regio-, and Stereoselective Cyclization of 1,3-Bis(trimethylsilyloxy)-1,3-butadienes with Functionalized Epoxides
  作者：Peter Langer、Tobias Eckardt

  DOI：10.1002/1521-3773(20001201)39:23<4343::aid-anie4343>3.0.co;2-q

  日期：2000.12.1
• 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.
• 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.