4,7-Bis(prop-2-enoxy)-1,3-dihydro-2-benzofuran | 1157854-59-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4,7-Bis(prop-2-enoxy)-1,3-dihydro-2-benzofuran
• CAS: 1157854-59-5
• 化学式: C₁₄H₁₆O₃
• 分子量: 232.279
• InChiKey: LQQSGYZTXYVPMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,7-Bis(prop-2-enoxy)-1,3-dihydro-2-benzofuran 在 N,N-二乙基苯胺 作用下， 反应 3.0h， 以93%的产率得到5,6-Bis(prop-2-enyl)-1,3-dihydro-2-benzofuran-4,7-diol
  参考文献：
  名称：

  Synthesis of 2,5-Dihydrofuran-Fused Quinones from Ether-Tethered Diiododiyne

  摘要：

  Biologically interesting 2,5-dihydrofuran-fused quinones were synthesized via the ruthenium-catalyzed [2 + 2 + 2] cycloaddition of an ether-tethered diiododiyne with alkynes, copper-catalyzed Ullmann coupling of the resultant fused p-diiodobenzenes with methanol or allyl alcohol, and subsequent oxidation of phenol derivatives. The double Claisen rearrangement of the bis(allyl) ether product furnished a diallylhydroquinone derivative, which underwent iron-catalyzed oxidation, ring-closing metathesis, and dehydrogenation to deliver 1,3-dihydronaphtho[2,3-c]furan-4,9-dione.

  DOI：

  10.1021/jo9005975
• 作为产物：
  描述：

  4,7-diiodo-1,3-dihydroisobenzofuran 、 烯丙醇 在 copper(l) iodide 、 1,10-菲罗啉 、 caesium carbonate 作用下， 以53%的产率得到4,7-Bis(prop-2-enoxy)-1,3-dihydro-2-benzofuran
  参考文献：
  名称：

  Synthesis of 2,5-Dihydrofuran-Fused Quinones from Ether-Tethered Diiododiyne

  摘要：

  Biologically interesting 2,5-dihydrofuran-fused quinones were synthesized via the ruthenium-catalyzed [2 + 2 + 2] cycloaddition of an ether-tethered diiododiyne with alkynes, copper-catalyzed Ullmann coupling of the resultant fused p-diiodobenzenes with methanol or allyl alcohol, and subsequent oxidation of phenol derivatives. The double Claisen rearrangement of the bis(allyl) ether product furnished a diallylhydroquinone derivative, which underwent iron-catalyzed oxidation, ring-closing metathesis, and dehydrogenation to deliver 1,3-dihydronaphtho[2,3-c]furan-4,9-dione.

  DOI：

  10.1021/jo9005975