2-[3-[3-(1,4-Dimethoxynaphthalen-2-yl)prop-2-ynoxy]prop-1-ynyl]-1,4-dimethoxynaphthalene | 1352640-95-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-[3-[3-(1,4-Dimethoxynaphthalen-2-yl)prop-2-ynoxy]prop-1-ynyl]-1,4-dimethoxynaphthalene
• CAS: 1352640-95-9
• 化学式: C₃₀H₂₆O₅
• 分子量: 466.533
• InChiKey: GNONNYZVUIAPPK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  2-[3-[3-(1,4-Dimethoxynaphthalen-2-yl)prop-2-ynoxy]prop-1-ynyl]-1,4-dimethoxynaphthalene 在 potassium tert-butylate 作用下， 以 甲苯 为溶剂， 以70%的产率得到4-(1,4-dimethoxy-naphthalen-2-yl)-5,10-dimethoxy-1,3-dihydro-anthra[2,3-c]furan
  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