(S)-2,2'-dimethoxy-1,1'-binaphthyl-5,5',6,6'-tetraol

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-2,2'-dimethoxy-1,1'-binaphthyl-5,5',6,6'-tetraol
• 英文别名: (S)-2,2'-dimethoxy-[1,1'-binaphthalene]-5,5',6,6'-tetraole；5-(5,6-Dihydroxy-2-methoxynaphthalen-1-yl)-6-methoxynaphthalene-1,2-diol
• 化学式: C₂₂H₁₈O₆
• 分子量: 378.381
• InChiKey: JFHMXYRSJMPJNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (S)-2,2'-dimethoxy-[1,1'-binaphthalene]-6,6'-diol 在 sodium dithionite 、 水 、 2-碘酰基苯甲酸 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 (S)-2,2'-dimethoxy-1,1'-binaphthyl-5,5',6,6'-tetraol
  参考文献：
  名称：

  Structural Reassignment of a Marine Metabolite from a Binaphthalenetetrol to a Tetrabrominated Diphenyl Ether

  摘要：

  The structure of a reported natural product isolate has been revised from (S)-2,2'-dimethoxy-[1,1'-binaphthalene]-5,5',6,6'-tetraol to a known tetrabrominated diphenyl ether. After total synthesis of the reported binaphthalenetetrol was accomplished via a key reduction of a binaphtho-ortho-quinone, comparison of the physical properties and NMR spectroscopic data of the synthetic material indicated that the structure of the natural product isolate was incorrect. Evaluation of the authentic natural product suggested the structure is a tetrabrominated diphenyl ether, likely 3,5-dibromo-2-(3,S-dibromo-2-methoxyphenoxy)phenol.

  DOI：

  10.1021/np300141t

文献信息

• Structural Reassignment of a Marine Metabolite from a Binaphthalenetetrol to a Tetrabrominated Diphenyl Ether
  作者：Erin E. Podlesny、Marisa C. Kozlowski

  DOI：10.1021/np300141t

  日期：2012.6.22

  The structure of a reported natural product isolate has been revised from (S)-2,2'-dimethoxy-[1,1'-binaphthalene]-5,5',6,6'-tetraol to a known tetrabrominated diphenyl ether. After total synthesis of the reported binaphthalenetetrol was accomplished via a key reduction of a binaphtho-ortho-quinone, comparison of the physical properties and NMR spectroscopic data of the synthetic material indicated that the structure of the natural product isolate was incorrect. Evaluation of the authentic natural product suggested the structure is a tetrabrominated diphenyl ether, likely 3,5-dibromo-2-(3,S-dibromo-2-methoxyphenoxy)phenol.