4,7-dimethoxyphthalan | 1157854-55-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: 4,7-dimethoxyphthalan
• 英文别名: 4,7-Dimethoxy-1,3-dihydro-2-benzofuran
• CAS: 1157854-55-1
• 化学式: C₁₀H₁₂O₃
• 分子量: 180.203
• InChiKey: MFABLPYGKWSQJB-UHFFFAOYSA-N

物化性质

• 熔点：
  88-89 °C
• 沸点：
  336.1±42.0 °C(Predicted)
• 密度：
  1.143±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 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-dimethoxyphthalan 在 ammonium cerium (IV) nitrate 、 水 作用下， 以 乙腈 为溶剂， 反应 0.17h， 以62%的产率得到isobenzofuran-4,7(1H,3H)-dione
  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 、 甲醇 在 copper(l) iodide 、 1,10-菲罗啉 、 potassium tert-butylate 作用下， 以79%的产率得到4,7-dimethoxyphthalan
  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

文献信息

• Synthesis of 2,5-Dihydrofuran-Fused Quinones from Ether-Tethered Diiododiyne
  作者：Yoshihiko Yamamoto、Ryousuke Takuma、Tomitaka Hotta、Ken Yamashita

  DOI：10.1021/jo9005975

  日期：2009.6.5

  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.