2,7-dimethoxy-3,6-di-tert-butylphenantrene | 139214-66-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 2,7-dimethoxy-3,6-di-tert-butylphenantrene
• 英文别名: 3,6-ditert-butyl-2,7-dimethoxyphenanthrene
• CAS: 139214-66-7
• 化学式: C₂₄H₃₀O₂
• 分子量: 350.501
• InChiKey: LIZTVLDJRRTCDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.61
• 重原子数：
  26.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  2,7-dimethoxy-3,6-di-tert-butylphenantrene 在 sodium hydride 、 乙硫醇 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以59%的产率得到2-hydroxy-7-methoxy-3,6-di-tert-butylphenantrene
  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：

  2-叔丁基-5-甲基苯甲醚 在 N-溴代丁二酰亚胺(NBS) 、 过氧化氢苯甲酰 、 溴 、 碘 、 potassium acetate 、 silver trifluoroacetate 、 铜 、 magnesium 、 1,2-二溴乙烷 作用下， 以 四氢呋喃 、 四氯化碳 、 二氯甲烷 为溶剂， 反应 7.17h， 生成 2,7-dimethoxy-3,6-di-tert-butylphenantrene
  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