Ellacene | 130136-65-1

• 分子结构分类: 有机化合物 - 碳氢化合物 - 多环烃
• 英文名称: Ellacene
• CAS: 130136-65-1
• 化学式: C₂₀H₂₈
• 分子量: 268.442
• InChiKey: DZSCEVRMFJFZTM-RKZNWXTNSA-N

物化性质

• 沸点：
  390.9±42.0 °C(Predicted)
• 密度：
  1.01±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.82
• 重原子数：
  20.0
• 可旋转键数：
  0.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  0.0
• 氢给体数：
  0.0
• 氢受体数：
  0.0

反应信息

• 作为产物：
  描述：

  Tetracyclo<11.5.2.0^2,13.0^2,16>eicosane-15,17,19-triol tris(methyl) xanthate 在 六甲基磷酰三胺 作用下， 反应 9.0h， 以91%的产率得到Ellacene
  参考文献：
  名称：

  General approach for the synthesis of polyquinenes via the Weiss reaction. 14. Synthesis of ellacene (1,10-decanotriquinacene) and studies of the proposed dimerization to a substituted dodecahedrane

  摘要：

  Ellacene 4, a tetracyclic 1,10-centrosubstituted triquinacene, has been synthesized via the Weiss reaction. The condensation of cyclododecane-1,2-dione (5) with di-tert-butyl 3-ketoglutarate (6) under aqueous alkaline conditions provided 13,15,16,18-tetrakis(tert-butoxycarbonyl)tricyclo[10.3.3.0(1,12)]octadecane-14,17-dione in the bisenol form 7 in 85 % yield. The bisenol ether 8 was regioselectively monoalkylated to furnish in 96 % yield the monoallyl ester 9 which was hydrolyzed to provide 13-allyltricyclo[10.3.3.0(1,12)]octadecane-14,17-dione (10). Intramolecular aldol reaction of the related diketo aldehyde 11 to furnish 17-hydroxytetracyclo[11.5.2.0(2,13).0(2,16)]eicosane-15,19-dione (12) was carried out under aqueous acidic conditions. The Lewis acid mediated (BH3/THF) reduction of the diketo alcohol provided the corresponding triol 13 in excellent yield. Conversion of the triol into the trisxanthate 21 followed by syn elimination (HMPA, 220-degrees-C) provided the desired triene 4 in 91 % yield. Attempted dimerization of 4 (ellacene) to a substituted dodecahedrane 3 under photochemical conditions and/or high pressure (130 kbar) has failed to generate 3 to date under conditions that did effect [2 + 2] dimerization of the parent, triquinacene.

  DOI：

  10.1021/jo00045a023