1-<(3,5-dimethoxy-4-hydroxyphenyl)methyl>-2-methyl-1-cyclohexene

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 1-<(3,5-dimethoxy-4-hydroxyphenyl)methyl>-2-methyl-1-cyclohexene
• 英文别名: 2,6-Dimethoxy-4-[(2-methylcyclohexen-1-yl)methyl]phenol
• 化学式: C₁₆H₂₂O₃
• 分子量: 262.349
• InChiKey: XFVVESUKQBAJAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-甲基-1-环己烯 、 2,6-二甲氧基酚 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 1.58h， 以51%的产率得到(4bS*,8aS*)-2,4-dimethoxy-3-hydroxy-4b-methyl-4b,5,6,7,8,8a-hexahydro-9H-fluorene
  参考文献：
  名称：

  Formal [3+2]cycloaddition of benzylic cations with alkenes

  摘要：

  The reaction of benzylic cations with styrenes affords dihydro(1H)indenes in good yield via a formal [3 + 2] atom cycloaddition. The cations were generated from quinone methides and benzylic alcohols. (E)-Styrenes participate in the reaction with remarkable stereoselectivity affording dihydro(1H)indenes with three stereogenic centers with >40:1 diastereoselectivity. A possible transition state for the reaction is discussed. Less activated alkenes such as dihydropyran and methylcyclohexene afforded cycloadducts in 66% and 51% yields, respectively.

  DOI：

  10.1021/jo00048a029

文献信息

• Formal [3+2]cycloaddition of benzylic cations with alkenes
  作者：Steven R. Angle、Damian O. Arnaiz

  DOI：10.1021/jo00048a029

  日期：1992.10

  The reaction of benzylic cations with styrenes affords dihydro(1H)indenes in good yield via a formal [3 + 2] atom cycloaddition. The cations were generated from quinone methides and benzylic alcohols. (E)-Styrenes participate in the reaction with remarkable stereoselectivity affording dihydro(1H)indenes with three stereogenic centers with >40:1 diastereoselectivity. A possible transition state for the reaction is discussed. Less activated alkenes such as dihydropyran and methylcyclohexene afforded cycloadducts in 66% and 51% yields, respectively.