(-)-ethyl 2,3,3a,4,5,6-hexahydrobenzofuran-7-carboxylate | 896449-24-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: (-)-ethyl 2,3,3a,4,5,6-hexahydrobenzofuran-7-carboxylate
• 英文别名: ethyl (3aR)-2,3,3a,4,5,6-hexahydro-1-benzofuran-7-carboxylate
• CAS: 896449-24-4
• 化学式: C₁₁H₁₆O₃
• 分子量: 196.246
• InChiKey: CAASQYFMTOCUAV-MRVPVSSYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• 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：

  (-)-ethyl 2,3,3a,4,5,6-hexahydrobenzofuran-7-carboxylate 在 silica gel 作用下， 以 正己烷 、 乙酸乙酯 为溶剂， 生成 ethyl 2,3,3a,4,5,6-hexahydrobenzofuran-7-carboxylate
  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
• 作为产物：
  描述：

  ethyl 2,3,3a,4,5,6-hexahydrobenzofuran-7-carboxylate 在 Candida antarctica lipase B 、 phosphate buffer 作用下， 以 甲苯 为溶剂， 反应 96.0h， 以34%的产率得到(-)-ethyl 2,3,3a,4,5,6-hexahydrobenzofuran-7-carboxylate
  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.