2-methoxy-3,9-dimethylphenanthrene | 142011-06-1

• 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-methoxy-3,9-dimethylphenanthrene
• CAS: 142011-06-1
• 化学式: C₁₇H₁₆O
• 分子量: 236.313
• InChiKey: XNUBSMLHFWYXQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.62
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  9.23
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  4,4-二甲氧基-3-甲基环己-2,5-二烯-1-酮 、 1-lithio-2-(1-methylethenyl)benzene 在 三氟化硼乙醚 、 水 作用下， 生成 2-methoxy-3,9-dimethylphenanthrene 、 2-methoxy-1,9-dimethylphenanthrene
  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

文献信息

• 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.