4-(2,5-Dimethoxyphenyl)-5,10-dimethoxy-1,3-dihydronaphtho[2,3-f][2]benzofuran | 1352641-07-6

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 芳基萘木脂素
• 英文名称: 4-(2,5-Dimethoxyphenyl)-5,10-dimethoxy-1,3-dihydronaphtho[2,3-f][2]benzofuran
• CAS: 1352641-07-6
• 化学式: C₂₆H₂₄O₅
• 分子量: 416.474
• InChiKey: MNSSGVNRZOTPFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(2,5-Dimethoxyphenyl)-5,10-dimethoxy-1,3-dihydronaphtho[2,3-f][2]benzofuran 在 ammonium cerium (IV) nitrate 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以70%的产率得到4-(3,6-Dioxocyclohexa-1,4-dien-1-yl)-1,3-dihydronaphtho[3,2-f][2]benzofuran-5,10-dione
  参考文献：
  名称：

  A facile Garratt–Braverman cyclization route to intercalative DNA-binding bis-quinones

  摘要：

  Bispropargyl ethers (both symmetrical and non-symmetrical) equipped with 1,4-dimethoxyaryl groups were synthesized. Under strongly basic conditions (KOBut/toluene/reflux), these ethers underwent Garratt-Braverman type cyclization to the tetramethoxy bi-aryl systems in high yields presumably via the bisallenes. The products could be successfully converted to the bis-quinones via CAN-mediated demethylation cum oxidation. This two-step protocol offers a simple route to bis-quinones, connected by C1-C2' bonds, in good yields. Fluorescence based EB-displacement assay, CD spectroscopy and viscosity measurements confirmed the DNA-binding ability of the synthesized quinones via intercalation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.10.030
• 作为产物：
  描述：

  2-[3-[3-(2,5-Dimethoxyphenyl)prop-2-ynoxy]prop-1-ynyl]-1,4-dimethoxynaphthalene 在 potassium tert-butylate 作用下， 以 甲苯 为溶剂， 生成 4-(2,5-Dimethoxyphenyl)-5,10-dimethoxy-1,3-dihydronaphtho[2,3-f][2]benzofuran 、 4-(1,4-Dimethoxynaphthalen-2-yl)-5,8-dimethoxy-1,3-dihydrobenzo[f][2]benzofuran
  参考文献：
  名称：

  A facile Garratt–Braverman cyclization route to intercalative DNA-binding bis-quinones

  摘要：

  Bispropargyl ethers (both symmetrical and non-symmetrical) equipped with 1,4-dimethoxyaryl groups were synthesized. Under strongly basic conditions (KOBut/toluene/reflux), these ethers underwent Garratt-Braverman type cyclization to the tetramethoxy bi-aryl systems in high yields presumably via the bisallenes. The products could be successfully converted to the bis-quinones via CAN-mediated demethylation cum oxidation. This two-step protocol offers a simple route to bis-quinones, connected by C1-C2' bonds, in good yields. Fluorescence based EB-displacement assay, CD spectroscopy and viscosity measurements confirmed the DNA-binding ability of the synthesized quinones via intercalation. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.10.030