1-formyl-2-(5-methoxy-2-furyl)cyclohexene | 851713-25-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-formyl-2-(5-methoxy-2-furyl)cyclohexene
• CAS: 851713-25-2
• 化学式: C₁₂H₁₄O₃
• 分子量: 206.241
• InChiKey: IQYGHACFGHNYSZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.81
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  39.44
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-formyl-2-(5-methoxy-2-furyl)cyclohexene 在 正丁基锂 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 正己烷 为溶剂， 反应 22.67h， 生成 (1Z,7Z,10Z)-12-Methoxy-15-oxa-tricyclo[10.2.1.0^2,7]pentadeca-1,7,10,13-tetraene-10,11-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  Synthesis of Furan-Bridged 10-Membered Rings through [8 + 2]-Cycloaddition of Dienylfurans and Acetylenic Esters

  摘要：

  The coupling of various dienylfurans with dimethyl acetylenedicarboxylate (DMAD) has been examined. In most cases this reaction proceeds via [8 + 2]-cycloaddition to afford furan-bridged 10-membered ring systems as a single diastereomer. Dienylfuran intermediates were generated using either a chromium carbene-based method or aldol-based methods. Reaction of [8 + 2]-cycloadducts with electrophilic reagents occurred selectively at the enol ether alkene.

  DOI：

  10.1021/ol050416n
• 作为产物：
  描述：

  2-呋甲醚 、 2-(i-propoxymethylene)cyclohexanone 以71%的产率得到1-formyl-2-(5-methoxy-2-furyl)cyclohexene
  参考文献：
  名称：

  Synthesis of Furan-Bridged 10-Membered Rings through [8 + 2]-Cycloaddition of Dienylfurans and Acetylenic Esters

  摘要：

  The coupling of various dienylfurans with dimethyl acetylenedicarboxylate (DMAD) has been examined. In most cases this reaction proceeds via [8 + 2]-cycloaddition to afford furan-bridged 10-membered ring systems as a single diastereomer. Dienylfuran intermediates were generated using either a chromium carbene-based method or aldol-based methods. Reaction of [8 + 2]-cycloadducts with electrophilic reagents occurred selectively at the enol ether alkene.

  DOI：

  10.1021/ol050416n