(1S,4S,4aS,7S,8aS)-1,4,4a,5,6,7,8,8a-octahydro-1,4a-dimethyl-7-(1-methylethenyl)naphthalene-1,4-diol | 1007586-33-5

• 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,4S,4aS,7S,8aS)-1,4,4a,5,6,7,8,8a-octahydro-1,4a-dimethyl-7-(1-methylethenyl)naphthalene-1,4-diol
• 英文别名: (1S,4S,4aS,6S,8aS)-4,8a-dimethyl-6-prop-1-en-2-yl-1,4a,5,6,7,8-hexahydronaphthalene-1,4-diol
• CAS: 1007586-33-5
• 化学式: C₁₅H₂₄O₂
• 分子量: 236.354
• InChiKey: VJHLBFGXENCHNL-YTFOTSKYSA-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：
  0.73
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (1S,4S,4aS,7S,8aS)-1,4,4a,5,6,7,8,8a-octahydro-1,4a-dimethyl-7-(1-methylethenyl)naphthalene-1,4-diol 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以91%的产率得到(4S,4aS,6S,8aS)-4a,5,6,7,8,8a-hexahydro-4-hydroxy-4,8a-dimethyl-6-(1-methylethenyl)naphthalen-1(4H)-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：

  (1aR,3R,3aS,6S,7aS,7bR)-octahydro-3-hydroxy-3a,7b-dimethyl-6-(1-methylethenyl)-naphtho[2,1-b]oxiren-2(1aH)-one 在 一水合肼 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以90%的产率得到(1S,4S,4aS,7S,8aS)-1,4,4a,5,6,7,8,8a-octahydro-1,4a-dimethyl-7-(1-methylethenyl)naphthalene-1,4-diol
  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.