2-Methyl-5-(2-vinyl-cyclohex-1-enyl)-furan | 851713-18-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: 2-Methyl-5-(2-vinyl-cyclohex-1-enyl)-furan
• 英文别名: 2-(2-Ethenylcyclohexen-1-yl)-5-methylfuran
• CAS: 851713-18-3
• 化学式: C₁₃H₁₆O
• 分子量: 188.269
• InChiKey: YGZQQESKXCYETL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  13.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-Methyl-5-(2-vinyl-cyclohex-1-enyl)-furan 、 丁炔二酸二甲酯 以 1,4-二氧六环 为溶剂， 反应 10.0h， 以77%的产率得到(1Z,7Z,10Z)-12-Methyl-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-甲基呋喃 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 12.67h， 生成 2-Methyl-5-(2-vinyl-cyclohex-1-enyl)-furan
  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

文献信息

• A novel stereoselective [8+2] double cycloaddition route to hydronaphthalene ring systems
  作者：Weijiang Ying、Lei Zhang、Paul A. Wiget、James W. Herndon

  DOI：10.1016/j.tetlet.2016.05.059

  日期：2016.7

  Substituted hydronaphthalenes where each of the ten carbons of the two-ring system contains functionality were obtained through a tandem [8+2] cycloaddition and base-catalyzed rearrangement process using dienylfurans and electron-deficient alkynes. If the [8+2] process is conducted under solvent-free conditions the process could be conducted in a single reaction flask without isolation of the chromatographically

  使用二烯基呋喃和缺电子炔烃通过串联[8+2]环加成和碱催化重排过程获得了双环系统的十个碳中的每一个都含有官能团的取代氢化萘。如果[8+2]过程在无溶剂条件下进行，则该过程可以在单个反应烧瓶中进行，而无需分离色谱敏感的[8+2]环加合物。针对将[8+2]环加合物转化为氢化萘的关键反应步骤，提出了一种涉及碱催化烯烃位置异构化然后进行非旋转电环闭环的机制。用路易斯酸处理后，产物经历选择性开环异构化过程。