(4aS,6R,8S,8aR)-4a,5,6,7,8,8a-hexahydro-8-hydroxy-4,8a-dimethyl-6-(1-methylethenyl)naphthalen-2(1H)-one | 1007586-28-8

• 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: (4aS,6R,8S,8aR)-4a,5,6,7,8,8a-hexahydro-8-hydroxy-4,8a-dimethyl-6-(1-methylethenyl)naphthalen-2(1H)-one
• 英文别名: (4aS,6R,8S,8aR)-8-hydroxy-4,8a-dimethyl-6-prop-1-en-2-yl-1,4a,5,6,7,8-hexahydronaphthalen-2-one
• CAS: 1007586-28-8
• 化学式: C₁₅H₂₂O₂
• 分子量: 234.338
• InChiKey: BOBYMJHYYKFZJJ-UQOMUDLDSA-N

物化性质

• 沸点：
  354.5±42.0 °C(Predicted)
• 密度：
  1.048±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  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 、 双氧水 作用下， 以 水 为溶剂， 以78%的产率得到(1aR,3aR,4S,6R,7aS,7bR)-octahydro-4-hydroxy-3a,7b-dimethyl-6-(1-methylethenyl)naphth[2,1-b]oxiren-2(1aH)-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
• 作为产物：
  描述：

  (4aR,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 作用下， 生成 (4aS,6R,8S,8aR)-4a,5,6,7,8,8a-hexahydro-8-hydroxy-4,8a-dimethyl-6-(1-methylethenyl)naphthalen-2(1H)-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