1,3,6,8-tetramethoxyphenanthrene-2,7-diol | 139253-14-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1,3,6,8-tetramethoxyphenanthrene-2,7-diol
• CAS: 139253-14-8
• 化学式: C₁₈H₁₈O₆
• 分子量: 330.337
• InChiKey: UMKHFNJIHWIIIQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3,3'-dihydroxy-2,2',4,4'-tetramethoxystilbene 在 碘苯二乙酸 作用下， 以 二氯甲烷 、 三氟乙酸 为溶剂， 反应 2.5h， 以7 mg的产率得到1,3,6,8-tetramethoxyphenanthrene-2,7-diol
  参考文献：
  名称：

  On the synthesis of a phenanthrene-2,7-quinone

  摘要：

  Oxidative coupling of 2,2',4,4'-tetramethoxystilbene-3,3'-diol 51 gave a 51% yield of 1,3,6,8-tetramethoxyphenanthrene-2,7-quinone 52, the first isolated example of a quinone of this type. Similar oxidation of the corresponding diphenylethane 55 gave the 9,10-dihydrophenanthrene-2,7-quinone 56. Attempts to synthesize the tetramethoxyphenanthrene-2,7-diol 25 from a 2,2'-bis(hydroxymethyl)hexamethoxybiphenyl precursor 28 were thwarted by the ease of intramolecular cyclization to 2,3,4,8,9,10-hexamethoxydibenz[c,e]oxepine 32. Selective demethylation of the 3- and 9-methoxy groups of this compound, and oxidation of the resulting diol 58 gave the dibenzoxepine quinone 59.The synthesis of 3,6-di-tert-butylphenanthrene-2,7-diol 3 is also described, but this could not be oxidized to the quinone. However, the preparation of 3,6-di-tert-butyl-9,10-dihydrophenanthrene-2,7-quinone 12 was successful.

  DOI：

  10.1039/p19910003033