rac-(1R,2R,3aR,4R,4aR,6R,7aR,8S,8aS,10R)-decahydro-1,2,4-(epimethanetriyl)-6,8-methano-s-indacen-5(1H)-one | 74999-10-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: rac-(1R,2R,3aR,4R,4aR,6R,7aR,8S,8aS,10R)-decahydro-1,2,4-(epimethanetriyl)-6,8-methano-s-indacen-5(1H)-one
• CAS: 74999-10-3
• 化学式: C₁₄H₁₆O
• 分子量: 200.28
• InChiKey: LPNOVPMOWSFKER-AZILCWPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.97
• 重原子数：
  15.0
• 可旋转键数：
  0.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  rac-(1R,2R,3aR,4R,4aR,6R,7aR,8S,8aS,10R)-decahydro-1,2,4-(epimethanetriyl)-6,8-methano-s-indacen-5(1H)-one 在 氢氧化钾 、 一水合肼 、 溶剂黄146 作用下， 生成 dodecahydro-1,2,4-(epimethanetriyl)-6,8-methano-s-indacene
  参考文献：
  名称：

  Synthesis of triamantane

  摘要：

  DOI：

  10.1021/jo01312a026
• 作为产物：
  描述：

  endo-cis-endo-heptacyclo(5.3.1.12,6.14,12.19,11.03,5.08,10)tetradecane 在 盐酸 、 potassium dichromate 、 sodium hydroxide 、 palladium on activated charcoal 、 硫酸 、 氢气 作用下， 以 乙醚 为溶剂， 反应 25.17h， 生成 rac-(1R,2R,3aR,4R,4aR,6R,7aR,8S,8aS,10R)-decahydro-1,2,4-(epimethanetriyl)-6,8-methano-s-indacen-5(1H)-one
  参考文献：
  名称：

  Reactions of heptacyclo[8.4.0.02,12.03,8.04,6.05,9.011,13]tetradecane (binor-s) with acids and alcohols catalyzed by Pd, Rh, and Pt complexes and some transformations of the compounds formed

  摘要：

  Reactions of heptacyclo[8.4.0.0(2,12).0(3,8).0(4.6.)0(5,9).0(11,13)]tetradecane (binor-s) 1 with proton-donor reagents were studied. Interaction of HCI and CF3COOH with 1 (25-degrees-C, 9-18 h) occurs at the cyclopropane ring (CPR) with regioselective cleavage of the C(4)-C(5) bond. With an excess of a proton-donor reagent the second CPR, whose opening proceeds non-selectively at both the C(Il)-C(12) and C(11)-C(13) bonds, enters the reaction. The addition of MeOH and AcOH to 1 proceeds only on boiling in the presence of such catalysts as PdCl2, RhCl3, and H2PtCl6. The chloro-, acetoxy-, methoxy-, dichloro-, and bistrifluoroacetoxy- derivatives (yields up to 95 %) were characterized by their C-13 NMR spectra.

  DOI：

  10.1007/bf00704004