(1S,4aS,5S,7S,8aS)-octahydro-8a-hydroxy-1,4a-dimethyl-7-(1-methylethenyl)-1,5-epoxynaphthalen-3(2H)-one | 1007586-29-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: (1S,4aS,5S,7S,8aS)-octahydro-8a-hydroxy-1,4a-dimethyl-7-(1-methylethenyl)-1,5-epoxynaphthalen-3(2H)-one
• CAS: 1007586-29-9
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: OQGMAPADUZADNN-PSWFKFNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.23
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  (4aS,6R,8S,8aR)-4a,5,6,7,8,8a-hexahydro-8-hydroxy-4,8a-dimethyl-6-(1-methylethenyl)naphthalen-2(1H)-one 在 sodium hydroxide 氧气 作用下， 以 甲醇 为溶剂， 反应 72.0h， 以45%的产率得到(1S,4aS,5S,7S,8aS)-octahydro-8a-hydroxy-1,4a-dimethyl-7-(1-methylethenyl)-1,5-epoxynaphthalen-3(2H)-one
  参考文献：
  名称：

  Enantiospecific Total Synthesis of Lairdinol A

  摘要：

  [GRAPHICS]The synthesis, of lairdinol A, a component of the host-selective phytotoxin depsilairdin, was achieved in 12 steps overall yield) without the use of protecting groups starting with the Diels-Alder reaction of (R)-carvone with 3-trimethylsilyloxy-1,3-pentadiene. The key step established the trans ring fusion by preferential epoxidation of a trans-fused enone in an equilibrating mixture of the cis-fused and transfused diastereomers (i.e., equivalent to a dynamic kinetic resolution of these isomers). The synthesis confirms the absolute configurations of lairdinol A and its enantiomer, cyperusol C.

  DOI：

  10.1021/jo7024465