2,3,4,8,9,10-hexamethoxydibenzoxepine | 139214-73-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异香豆素
• 英文名称: 2,3,4,8,9,10-hexamethoxydibenzoxepine
• 英文别名: 2,3,4,8,9,10-Hexamethoxy-5,7-dihydro-dibenzoxepin；2,3,4,8,9,10-Hexamethoxy-5,7-dihydro-dibenz[c.e]oxepin；2,3,4,8,9,10-hexamethoxy-5,7-dihydrobenzo[d][2]benzoxepine
• CAS: 139214-73-6
• 化学式: C₂₀H₂₄O₇
• 分子量: 376.406
• InChiKey: LHRCQGIZYQUIJW-UHFFFAOYSA-N

物化性质

• 沸点：
  537.5±50.0 °C(Predicted)
• 密度：
  1.180±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.44
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  64.61
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2,3,4,8,9,10-hexamethoxydibenzoxepine 在 甲基碘化镁 、 silver(l) oxide 作用下， 以 乙醚 、 氯仿 、 甲苯 为溶剂， 反应 0.5h， 生成 2,4,8,10-tetramethoxydibenzoxepine-3,9-quinone
  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
• 作为产物：
  描述：

  methyl 6-bromo-2,3,4-trimethoxybenzoate 在 sodium hydroxide 、 lithium aluminium tetrahydride 、 铜 、 potassium carbonate 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.25h， 生成 2,3,4,8,9,10-hexamethoxydibenzoxepine
  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