(1S*,2S*,3R*)-5,7-dimthoxy-3-ethyl-6-hydroxy-2-methyl-1-phenyl-2,3-dihydroindene | 127311-24-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: (1S*,2S*,3R*)-5,7-dimthoxy-3-ethyl-6-hydroxy-2-methyl-1-phenyl-2,3-dihydroindene
• 英文别名: (1R,2S,3S)-1-ethyl-4,6-dimethoxy-2-methyl-3-phenyl-2,3-dihydro-1H-inden-5-ol
• CAS: 127311-24-4；127419-14-1；143730-97-6；143730-98-7
• 化学式: C₂₀H₂₄O₃
• 分子量: 312.409
• InChiKey: VIFPBLBXODZOID-QEORTHHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 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：

  4-丙基-2,6-二甲氧基苯酚 在 zinc(II) chloride 、 silver(l) oxide 作用下， 以 氘代氯仿 、 二氯甲烷 为溶剂， 反应 1.25h， 生成 (1S*,2S*,3R*)-5,7-dimthoxy-3-ethyl-6-hydroxy-2-methyl-1-phenyl-2,3-dihydroindene
  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

• 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
• 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.