(3R,4aS,5S,7R,8aR)-hexahydro-7-hydroxy-5,8a-dimethyl-3-(1-methylethenyl)naphthalene-1,6(2H,5H)-dione | 1007586-24-4

• 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: (3R,4aS,5S,7R,8aR)-hexahydro-7-hydroxy-5,8a-dimethyl-3-(1-methylethenyl)naphthalene-1,6(2H,5H)-dione
• 英文别名: (3R,4aS,5S,7R,8aR)-7-hydroxy-5,8a-dimethyl-3-prop-1-en-2-yl-3,4,4a,5,7,8-hexahydro-2H-naphthalene-1,6-dione
• CAS: 1007586-24-4
• 化学式: C₁₅H₂₂O₃
• 分子量: 250.338
• InChiKey: YCVKIYVIBXEEHB-VINAVUOLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3R,4aS,5S,7R,8aR)-hexahydro-7-hydroxy-5,8a-dimethyl-3-(1-methylethenyl)naphthalene-1,6(2H,5H)-dione 在 草酰氯 、 二甲基亚砜 、 N,N-二异丙基乙胺 、 silica gel 、 三乙胺 作用下， 以 二氯甲烷 、 正己烷 、 乙酸乙酯 为溶剂， 以95%的产率得到(3R,4aS,8aR)-3,4,4a,8a-tetrahydro-6-hydroxy-5,8a-dimethyl-3-(1-methylethenyl)-1,7(2H,8H)-naphthalenedione
  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：

  [(1S,4aR,7R,8aS)-1,4a-dimethyl-7-prop-1-en-2-yl-5-trimethylsilyloxy-4,7,8,8a-tetrahydro-1H-naphthalen-2-yl]oxy-trimethylsilane 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以2.09 g的产率得到(3R,4aS,5S,7R,8aR)-hexahydro-7-hydroxy-5,8a-dimethyl-3-(1-methylethenyl)naphthalene-1,6(2H,5H)-dione
  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