(3R,4aS,8aR)-3,4,4a,8a-tetrahydro-5,8a-dimethyl-3-(1-methylethenyl)-1,7(2H,8H)-naphthalenedione | 1007586-27-7

• 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: (3R,4aS,8aR)-3,4,4a,8a-tetrahydro-5,8a-dimethyl-3-(1-methylethenyl)-1,7(2H,8H)-naphthalenedione
• 英文别名: (3R,4aS,8aR)-5,8a-dimethyl-3-prop-1-en-2-yl-3,4,4a,8-tetrahydro-2H-naphthalene-1,7-dione
• CAS: 1007586-27-7
• 化学式: C₁₅H₂₀O₂
• 分子量: 232.323
• InChiKey: CZSRWQGUVGZDJQ-OSAQELSMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R,4aS,8aR)-3,4,4a,8a-tetrahydro-5,8a-dimethyl-3-(1-methylethenyl)-1,7(2H,8H)-naphthalenedione 在 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以80%的产率得到(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
• 作为产物：
  描述：

  (3R,4aS,8aR)-1,2,3,4,4a,7,8,8a-octahydro-5,8a-dimethyl-1,7-dioxo-3-(1-methylethenyl)naphthalen-6-yl trifluoromethanesulfonate 在 四(三苯基膦)钯 三乙基硅烷 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (3R,4aR,8aR)-3,4,4a,8a-tetrahydro-5,8a-dimethyl-3-(1-methylethenyl)-1,7(2H,8H)-naphthalenedione 、 (3R,4aS,8aR)-3,4,4a,8a-tetrahydro-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

文献信息

• Enantiospecific Total Synthesis of Lairdinol A
  作者：Sandip G. Pardeshi、Dale E. Ward

  DOI：10.1021/jo7024465

  日期：2008.2.1

  [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.