1,1a,2,3,4,4a,5,5a,6,7,8,8a,9,10-tetradecahydro-1:4,5:8-dimethanoanthracene-9,10-diol | 101271-57-2

• 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: 1,1a,2,3,4,4a,5,5a,6,7,8,8a,9,10-tetradecahydro-1:4,5:8-dimethanoanthracene-9,10-diol
• CAS: 101271-57-2
• 化学式: C₁₆H₂₄O₂
• 分子量: 248.365
• InChiKey: ZLLCWMLUVPYBOZ-WALRCSFASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.05
• 重原子数：
  18.0
• 可旋转键数：
  0.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.46
• 氢给体数：
  2.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1,1a,2,3,4,4a,5,5a,6,7,8,8a,9,10-tetradecahydro-1:4,5:8-dimethanoanthracene-9,10-diol 在 磷酸 、 氧气 、 4-甲基苯磺酸吡啶 、 四氯化钛 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 28.0h， 生成 (1S,4R,5R,8S)-1,2,3,4,5,6,7,8-octahydro-1,4:5,8-dimethanoanthracene-9-carboxaldehyde (1R,2R)-diphenylethylene ketal
  参考文献：
  名称：

  Catalytic asymmetric epoxidation of unfunctionalized alkenes using the first D4-symmetric metallotetraphenylporphyrin

  摘要：

  The condensation of the resolved C2-symmetric benzaldehyde, 1,2,3,4,5,6,7,8-octahydro-1:4,5:8-dimethanoanthracene-9-carboxaldehyde, with pyrrole produced a new chiral tetraphenylporphyrin exhibiting D4 symmetry. A manganese chloride complex of this porphyrin was used as a catalyst (0.5 mol %) for the asymmetric epoxidation of aromatic-substituted alkenes in the presence of excess sodium hypochlorite, providing for terminal or Z alkene yields above 90% and enantioselectivities ranging from 41 to 76% ee.

  DOI：

  10.1021/jo00018a008
• 作为产物：
  描述：

  (1R,4S,4aR,5S,8R,8aS,9aS,10aR)-1,4,4a,5,8,8a,9a,10a-octahydro-1,4:5,8-dimethanoanthracene-9,10-dione 在 palladium on activated charcoal sodium tetrahydroborate 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 23.0 ℃ 、289.58 kPa 条件下， 反应 17.0h， 生成 1,1a,2,3,4,4a,5,5a,6,7,8,8a,9,10-tetradecahydro-1:4,5:8-dimethanoanthracene-9,10-diol
  参考文献：
  名称：

  Catalytic asymmetric epoxidation of unfunctionalized alkenes using the first D4-symmetric metallotetraphenylporphyrin

  摘要：

  The condensation of the resolved C2-symmetric benzaldehyde, 1,2,3,4,5,6,7,8-octahydro-1:4,5:8-dimethanoanthracene-9-carboxaldehyde, with pyrrole produced a new chiral tetraphenylporphyrin exhibiting D4 symmetry. A manganese chloride complex of this porphyrin was used as a catalyst (0.5 mol %) for the asymmetric epoxidation of aromatic-substituted alkenes in the presence of excess sodium hypochlorite, providing for terminal or Z alkene yields above 90% and enantioselectivities ranging from 41 to 76% ee.

  DOI：

  10.1021/jo00018a008

文献信息

• Catalytic asymmetric epoxidation of unfunctionalized alkenes using the first D4-symmetric metallotetraphenylporphyrin
  作者：Ronald L. Halterman、Shyi Tai Jan

  DOI：10.1021/jo00018a008

  日期：1991.8

  The condensation of the resolved C2-symmetric benzaldehyde, 1,2,3,4,5,6,7,8-octahydro-1:4,5:8-dimethanoanthracene-9-carboxaldehyde, with pyrrole produced a new chiral tetraphenylporphyrin exhibiting D4 symmetry. A manganese chloride complex of this porphyrin was used as a catalyst (0.5 mol %) for the asymmetric epoxidation of aromatic-substituted alkenes in the presence of excess sodium hypochlorite, providing for terminal or Z alkene yields above 90% and enantioselectivities ranging from 41 to 76% ee.