(1R,4S,4aR,5R,6S,7R,8S,8aS)-6,7-(isopropylidenedioxy)-1,4,4a,5,6,7,8,8a-octahydro-1,4-methano-naphthalene-5,8-diol | 1190083-86-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,4S,4aR,5R,6S,7R,8S,8aS)-6,7-(isopropylidenedioxy)-1,4,4a,5,6,7,8,8a-octahydro-1,4-methano-naphthalene-5,8-diol
• 英文别名: (1S,2R,3R,4S,8R,9S,10S,11R)-6,6-dimethyl-5,7-dioxatetracyclo[9.2.1.02,10.04,8]tetradec-12-ene-3,9-diol
• CAS: 1190083-86-3
• 化学式: C₁₄H₂₀O₄
• 分子量: 252.31
• InChiKey: UCRAJZOMPJEEHD-RKPOYUIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,4S,4aR,5R,6S,7R,8S,8aS)-6,7-(isopropylidenedioxy)-1,4,4a,5,6,7,8,8a-octahydro-1,4-methano-naphthalene-5,8-diol 在 C₃₂H₃₆IrNO₂S 、 potassium tert-butylate 作用下， 以 环己酮 为溶剂， 反应 24.0h， 以62%的产率得到(1R,4S,4aR,5R,6S,7S,8aS)-5-trihydroxy-6,7-O-isopropylidenedioxy-1,4,4a,5,6,7,8,8a-octahydro-endo-1,4-methanonaphthalen-8-one
  参考文献：
  名称：

  Ir-Catalyzed Oxidative Desymmetrization of meso-Diols

  摘要：

  The catalytic oxidative desymmetrization of meso-diols was realized using a chiral iridium catalyst. In particular, the reaction is effective for the cyclic diols to give the corresponding hydroxy ketones in high chemical yields with high ee's. With this reaction as a key step, a short-step synthesis of common intermediate of ottelione and scyphostatin was achieved.

  DOI：

  10.1021/ol9016436
• 作为产物：
  描述：

  (1RS,2SR,3SR,4SR,4aRS,5SR,6RS,7RS,8RS,8aRS)-3-bromo-2,8-epoxy-6,7-(isopropylidenedioxy)decahydro-1,4-methano-naphthalen-5-ol 在 溶剂黄146 、 锌 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以88%的产率得到(1R,4S,4aR,5R,6S,7R,8S,8aS)-6,7-(isopropylidenedioxy)-1,4,4a,5,6,7,8,8a-octahydro-1,4-methano-naphthalene-5,8-diol
  参考文献：
  名称：

  Ir-Catalyzed Oxidative Desymmetrization of meso-Diols

  摘要：

  The catalytic oxidative desymmetrization of meso-diols was realized using a chiral iridium catalyst. In particular, the reaction is effective for the cyclic diols to give the corresponding hydroxy ketones in high chemical yields with high ee's. With this reaction as a key step, a short-step synthesis of common intermediate of ottelione and scyphostatin was achieved.

  DOI：

  10.1021/ol9016436