(1S*,2S*,3R*)-3-ethyl-6-hydroxy-5-methoxy-1-(4-methoxyphenyl)-2-methyl-2,3-dihydroindene

• 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*)-3-ethyl-6-hydroxy-5-methoxy-1-(4-methoxyphenyl)-2-methyl-2,3-dihydroindene
• 英文别名: (1R,2S,3S)-1-ethyl-6-methoxy-3-(4-methoxyphenyl)-2-methyl-2,3-dihydro-1H-inden-5-ol
• 化学式: C₂₀H₂₄O₃
• 分子量: 312.409
• InChiKey: NGFFXTIOUMZEKW-VHPWJVAPSA-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-(1-羟基丙基)-2-甲氧基苯酚 、 茴香烯 在 四氯化锡 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (1R*,2S*,3R*)-3-ethyl-6-hydroxy-5-methoxy-1-(4-methyloxyphenyl)-2-methyl-2,3-dihydroindene 、 (1S*,2S*,3R*)-3-ethyl-6-hydroxy-5-methoxy-1-(4-methoxyphenyl)-2-methyl-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

• Gold-Catalyzed Formal (3+2) Cycloaddition in an Ionic Liquid: Environmentally Friendly and Stereoselective Synthesis of Polysubstituted Indanes from Benzylic Alcohols and 1-Phenylpropenes
  作者：Nobuyoshi Morita、Osamu Tamura、Hitomi Chiaki、Kanae Ikeda、Kosaku Tanaka、Yoshimitsu Hashimoto

  DOI：10.1055/a-2002-4122

  日期：——

  A gold-catalyzed formal (3+2) cycloaddition of benzylic alcohols with 1-phenylpropenes in an ionic liquid permits the environmentally friendly stereoselective synthesis of polysubstituted indanes in good yields and with high selectivity. The gold catalyst can be recycled at least five times.

  在离子液体中，金催化的苄醇与 1-苯基丙烯的形式 (3+2) 环加成允许以良好的收率和高选择性环境友好地立体选择性合成多取代的茚满。金催化剂至少可以循环使用五次。