spiro[1,3-dioxolane-2,7'-2,3,4,4a,5,6,8,8a-octahydro-1H-naphthalene]

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: spiro[1,3-dioxolane-2,7'-2,3,4,4a,5,6,8,8a-octahydro-1H-naphthalene]
• 化学式: C₁₂H₂₀O₂
• 分子量: 196.29
• InChiKey: ZZUDEEZIBZJMHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

文献信息

• PROCESS FOR PREPARING OPTICALLY ACTIVE ANTROCIN
  申请人：TAI Dar-fu

  公开号：US20130096324A1

  公开（公告）日：2013-04-18

  The present invention relates to a process of preparation of optically active antrocin. At first, to introduce the correct configuration of trans-decalone, alkyl aluminum/TMSCN was used to react with decalenone. The resulting racemic nitrile-decalone was resolved with chiral diol by ketalization to produce two chromatography separable diasteromers. After a simple column chromatography, optically pure compounds were obtained. Formylation was a critical step for the lactone formation. The rest of the synthesis is straight forward through oxidation and olefination. Accordingly, the total synthesis was completed in 10 steps with 7% overall yield from commercially available 6-methoxy-2-tetralone.

  本发明涉及一种制备光学活性antrocin的过程。首先，使用烷基铝/TMSCN引入反式十环酮的正确构型，与十环酮反应得到外消旋的腈基十环酮，再通过缩酮反应与手性二醇反应，得到两个可通过色谱分离的对映异构体。经过简单的柱层析后，得到光学纯的化合物。甲酰化是内酯形成的关键步骤。其余的合成步骤通过氧化和烯丙基化是直截了当的。因此，从商业可得的6-甲氧基-2-四环酮开始，经过10个步骤，总产率为7％，完成了总合成。