[(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 | 1007586-41-5

• 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: [(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
• CAS: 1007586-41-5
• 化学式: C₂₁H₃₈O₂Si₂
• 分子量: 378.703
• InChiKey: NUGNOXFFYMKDJT-TWFHAPMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.72
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  三甲基氯硅烷 、 (3R,4aS,5S,8aR)-hexahydro-5,8a-dimethyl-3-(1-methylethenyl)naphthalene-1,6(2H,5H)-dione 在 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 生成 [(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
  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