methyl (5-ethyldihydrofuran-2(3H)-ylidene)acetate

• 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: methyl (5-ethyldihydrofuran-2(3H)-ylidene)acetate
• 英文别名: methyl (2E)-2-(5-butyloxolan-2-ylidene)acetate
• 化学式: C₁₁H₁₈O₃
• 分子量: 198.262
• InChiKey: DDJDITCTBYUQDF-CSKARUKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  methyl (5-ethyldihydrofuran-2(3H)-ylidene)acetate 在 三溴化硼 、 水 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到6-bromo-3-oxodecanoic acid methyl ester
  参考文献：
  名称：

  2-亚烷基四氢呋喃与三溴化硼的反应：应用“环化-开环”策略化学和区域选择性合成 6-Bromo-3-oxoalkanoates

  摘要：

  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。

  DOI：

  10.1055/s-2004-830893
• 作为产物：
  描述：

  丁基环氧乙烷 、 1,3-bis(trimethylsiloxy)-1-methoxybuta-1,3-diene 在 4 A molecular sieve 、 四氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 21.0h， 以36%的产率得到methyl (5-ethyldihydrofuran-2(3H)-ylidene)acetate
  参考文献：
  名称：

  Enantioselective synthesis of 2-alkylidenetetrahydrofurans based on a ‘cyclization/enzymatic resolution’ strategy

  摘要：

  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.

  DOI：

  10.1016/j.tetasy.2006.03.006

文献信息

• 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.
• 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。