2,2',6,6'-Tetraacetoxy-1,1'-binaphthalene

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,2',6,6'-Tetraacetoxy-1,1'-binaphthalene
• 英文别名: [6-Acetyloxy-5-(3,7-diacetyloxynaphthalen-1-yl)naphthalen-2-yl] acetate
• 化学式: C₂₈H₂₂O₈
• 分子量: 486.478
• InChiKey: BCLWLEXULRTRSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  2,6-萘二酚 、 乙酸酐 在 sodium acetate 、 三氯化铁 作用下， 生成 2,2',6,6'-Tetraacetoxy-1,1'-binaphthalene 、 [6-Acetyloxy-5-[2,6-diacetyloxy-5-(2,6-diacetyloxynaphthalen-1-yl)naphthalen-1-yl]naphthalen-2-yl] acetate
  参考文献：
  名称：

  Anodic Oxidation of 2,6-Dihydroxynaphthalene1 and Structural Characterization of the Oligomers

  摘要：

  Potential-controlled electrochemical oxidation of 2,6-dihydroxynaphthalene (1) produced two oligomers, which were characterized by spectrometric (H-1 and C-13 NMR, IR, and UV) and electrochemical (CV) methods. The H-1 NMR chemical shifts of the peracetyl derivatives, which showed different values for the acetoxy groups attached at the terminal and the internal positions of the chain, were essential for structure determination of the products. Peracetyl derivatives of the monomer 1a, dimer 2a, and two stereoisomeric trimers 3a and 4a served as models in the spectrometric characterization and structure determination of the oligomers. The product isolated from the anolyte was a mixture of oligomers 5 composed of an average of nine monomer units. The spectroscopic data for the product extracted from the anode 6 suggested that its molecular weight was much higher. In all investigated compounds, the naphthalene rings were proven to be linked at the 1- and 5-positions. The solubility and the spectroscopic data of both oligomers suggested that the chains were not cross-linked. Similar cyclic voltammetric (CV) behavior was found for poly(2,6-dihydroxynaphthalene) films prepared either by the dip-coating technique from a solution of 6 or by the previously reported electrochemical deposition from a solution of 1 by the potential-scanning technique.(2)

  DOI：

  10.1021/jo00094a045

文献信息

• Anodic Oxidation of 2,6-Dihydroxynaphthalene1 and Structural Characterization of the Oligomers
  作者：Gustavo H. Marin、Vaclav Horak

  DOI：10.1021/jo00094a045

  日期：1994.7

  Potential-controlled electrochemical oxidation of 2,6-dihydroxynaphthalene (1) produced two oligomers, which were characterized by spectrometric (H-1 and C-13 NMR, IR, and UV) and electrochemical (CV) methods. The H-1 NMR chemical shifts of the peracetyl derivatives, which showed different values for the acetoxy groups attached at the terminal and the internal positions of the chain, were essential for structure determination of the products. Peracetyl derivatives of the monomer 1a, dimer 2a, and two stereoisomeric trimers 3a and 4a served as models in the spectrometric characterization and structure determination of the oligomers. The product isolated from the anolyte was a mixture of oligomers 5 composed of an average of nine monomer units. The spectroscopic data for the product extracted from the anode 6 suggested that its molecular weight was much higher. In all investigated compounds, the naphthalene rings were proven to be linked at the 1- and 5-positions. The solubility and the spectroscopic data of both oligomers suggested that the chains were not cross-linked. Similar cyclic voltammetric (CV) behavior was found for poly(2,6-dihydroxynaphthalene) films prepared either by the dip-coating technique from a solution of 6 or by the previously reported electrochemical deposition from a solution of 1 by the potential-scanning technique.(2)