2,6-dimethoxy-4-propylidene-2,5-cyclohexadien-1-one | 24760-60-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,6-dimethoxy-4-propylidene-2,5-cyclohexadien-1-one
• 英文别名: 2,6-Dimethoxy-4-propylidenecyclohexa-2,5-dien-1-one
• CAS: 24760-60-9
• 化学式: C₁₁H₁₄O₃
• 分子量: 194.23
• InChiKey: OCPNIGBUZLTBHM-UHFFFAOYSA-N

物化性质

• 沸点：
  373.6±42.0 °C(Predicted)
• 密度：
  1.07±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  异丁香酚 、 2,6-dimethoxy-4-propylidene-2,5-cyclohexadien-1-one 在 zinc(II) chloride 作用下， 以51%的产率得到
  参考文献：
  名称：

  Synthesis of dihydro-1H-indenes via a formal 3 + 2 cycloaddition of para-quinone methides and styrenes

  摘要：

  DOI：

  10.1021/jo00299a003
• 作为产物：
  描述：

  4-丙基-2,6-二甲氧基苯酚 在 silver(l) oxide 作用下， 以 氘代氯仿 为溶剂， 反应 0.17h， 生成 2,6-dimethoxy-4-propylidene-2,5-cyclohexadien-1-one
  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+3]- and [3+2]-cycloadditions of allylsilanes with benzylic cations
  作者：Steven R. Angle、Jim P. Boyce

  DOI：10.1016/s0040-4039(00)78246-3

  日期：1994.8

  Allylsilanes serve as three-carbon dipole equivalents for the formation of tetrahydronaphthalenes via Lewis-acid promoted formal [3+3]-cycloadditions with benzylic cations. A competing [3+2]-pathway resulted in the formation of dihydro(1H)indenes. Both quinone methides and benzylic alcohols were used as precursors to the benzylic cations.
• 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.
• Synthesis of dihydro-1H-indenes via a formal 3 + 2 cycloaddition of para-quinone methides and styrenes
  作者：Steven R. Angle、Damian O. Arnaiz

  DOI：10.1021/jo00299a003

  日期：1990.6