4,4-dimethoxy-1-(2-ethenyl-4-methoxyphenyl)-1-hydroxy-2,5-cyclohexadiene | 171512-98-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4,4-dimethoxy-1-(2-ethenyl-4-methoxyphenyl)-1-hydroxy-2,5-cyclohexadiene
• 英文别名: 1-(2-Ethenyl-4-methoxyphenyl)-4,4-dimethoxycyclohexa-2,5-dien-1-ol
• CAS: 171512-98-4
• 化学式: C₁₇H₂₀O₄
• 分子量: 288.343
• InChiKey: USUIFBVUGBEAPE-UHFFFAOYSA-N

物化性质

• 沸点：
  432.8±45.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,4-dimethoxy-1-(2-ethenyl-4-methoxyphenyl)-1-hydroxy-2,5-cyclohexadiene 在 四氯化锡 作用下， 以 苯 为溶剂， 以55%的产率得到2,7-二甲氧基菲
  参考文献：
  名称：

  Oxygenated phenanthrenes via quinol ketals: Cyclization vs. migration

  摘要：

  2-methoxyphenanthrenes were prepared by reaction of lithiated 2-bromostyrenes with quinone monoketals followed by acid-mediated cyclization of the resulting p-arylquinol ketals. Substitution at the bromostyrene side-chain or the quinone monoketal ring had only a modest effect on yields, but oxygen substitution on the bromostyrene aromatic nucleus resulted in a competing 1,2-aryl migration arising during the quinol ketal cyclization step. The extent of this rearrangement was found to be a function of the Lewis acid/solvent system employed.

  DOI：

  10.1016/0040-4020(95)00593-w
• 作为产物：
  描述：

  4,4-二甲氧基-2,5-环己二烯-1-酮 、 1-溴-4-甲氧基-2-乙烯基苯 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以59%的产率得到4,4-dimethoxy-1-(2-ethenyl-4-methoxyphenyl)-1-hydroxy-2,5-cyclohexadiene
  参考文献：
  名称：

  Oxygenated phenanthrenes via quinol ketals: Cyclization vs. migration

  摘要：

  2-methoxyphenanthrenes were prepared by reaction of lithiated 2-bromostyrenes with quinone monoketals followed by acid-mediated cyclization of the resulting p-arylquinol ketals. Substitution at the bromostyrene side-chain or the quinone monoketal ring had only a modest effect on yields, but oxygen substitution on the bromostyrene aromatic nucleus resulted in a competing 1,2-aryl migration arising during the quinol ketal cyclization step. The extent of this rearrangement was found to be a function of the Lewis acid/solvent system employed.

  DOI：

  10.1016/0040-4020(95)00593-w