4,4-dimethoxy-1-(2-ethenylphenyl)-1-hydroxy-2,5-cyclohexadiene | 142011-03-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,4-dimethoxy-1-(2-ethenylphenyl)-1-hydroxy-2,5-cyclohexadiene
• 英文别名: 4,4-Dimethoxy-1-(2-vinylphenyl)-2,5-cyclohexadien-1-ol；1-(2-ethenylphenyl)-4,4-dimethoxycyclohexa-2,5-dien-1-ol
• CAS: 142011-03-8
• 化学式: C₁₆H₁₈O₃
• 分子量: 258.317
• InChiKey: NLINCCBFKNTJKQ-UHFFFAOYSA-N

物化性质

• 沸点：
  398.4±42.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,4-dimethoxy-1-(2-ethenylphenyl)-1-hydroxy-2,5-cyclohexadiene 在 三氟化硼乙醚 作用下， 以 甲醇 为溶剂， 以93%的产率得到2-甲氧基菲
  参考文献：
  名称：

  A convergent approach to substituted phenanthrenes via quinol ketals

  摘要：

  Reaction of 2'-lithiostyrenes with p-benzoquinone monoketals gives p-quinol ketals which undergo Lewis acid-catalyzed cyclization and aromatization, affording 2-methoxyphenanthrenes.

  DOI：

  10.1016/s0040-4039(00)74186-4
• 作为产物：
  描述：

  4,4-二甲氧基-2,5-环己二烯-1-酮 、 2-溴苯乙烯 在 正丁基锂 作用下， 以 四氢呋喃 为溶剂， 以74%的产率得到4,4-dimethoxy-1-(2-ethenylphenyl)-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

文献信息

• A convergent approach to substituted phenanthrenes via quinol ketals
  作者：Tina M. Marks、Gary W. Morrow

  DOI：10.1016/s0040-4039(00)74186-4

  日期：1992.4

  Reaction of 2'-lithiostyrenes with p-benzoquinone monoketals gives p-quinol ketals which undergo Lewis acid-catalyzed cyclization and aromatization, affording 2-methoxyphenanthrenes.
• Oxygenated phenanthrenes via quinol ketals: Cyclization vs. migration
  作者：Gary W. Morrow、Tina M. Marks、Debra L. Sear

  DOI：10.1016/0040-4020(95)00593-w

  日期：1995.9

  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.