(4S,4aS,6S,8aS)-octahydro-4-hydroxy-4,8a-dimethyl-6-(1-methylethenyl)naphthalen-1(2H)-one | 1007586-51-7

• 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: (4S,4aS,6S,8aS)-octahydro-4-hydroxy-4,8a-dimethyl-6-(1-methylethenyl)naphthalen-1(2H)-one
• 英文别名: (4S,4aS,6S,8aS)-4-hydroxy-4,8a-dimethyl-6-prop-1-en-2-yl-3,4a,5,6,7,8-hexahydro-2H-naphthalen-1-one
• CAS: 1007586-51-7
• 化学式: C₁₅H₂₄O₂
• 分子量: 236.354
• InChiKey: APRONAGXQZHIMW-JURCDPSOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  (4S,4aS,6S,8aS)-octahydro-4-hydroxy-4,8a-dimethyl-6-(1-methylethenyl)naphthalen-1(2H)-one 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.17h， 以98%的产率得到lairdinol A
  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：

  (4S,4aS,6S,8aS)-4a,5,6,7,8,8a-hexahydro-4-hydroxy-4,8a-dimethyl-6-(1-methylethenyl)naphthalen-1(4H)-one 在 Stryker's reagent 二甲基苯基硅烷 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以88%的产率得到(4S,4aS,6S,8aS)-octahydro-4-hydroxy-4,8a-dimethyl-6-(1-methylethenyl)naphthalen-1(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