(1S,2S,4aS,8aR)-1-(2-hydroxyethyl)-4a-(hydroxymethyl)-2,7,7-trimethyl-3,4,5,6,8,8a-hexahydronaphthalene-1,2-diol | 918436-92-7

• 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: (1S,2S,4aS,8aR)-1-(2-hydroxyethyl)-4a-(hydroxymethyl)-2,7,7-trimethyl-3,4,5,6,8,8a-hexahydronaphthalene-1,2-diol
• CAS: 918436-92-7
• 化学式: C₁₆H₃₀O₄
• 分子量: 286.412
• InChiKey: OTEYYYODKWHPJI-BVUBDWEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  80.9
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1S,2S,4aS,8aR)-1-(2-hydroxyethyl)-4a-(hydroxymethyl)-2,7,7-trimethyl-3,4,5,6,8,8a-hexahydronaphthalene-1,2-diol 、 乙酸乙烯酯 在 Candida antarctica lipase 作用下， 反应 24.0h， 以95%的产率得到2-[(1S,2S,4aS,8aR)-1,2-dihydroxy-4a-(hydroxymethyl)-2,7,7-trimethyl-3,4,5,6,8,8a-hexahydronaphthalen-1-yl]ethyl acetate
  参考文献：
  名称：

  Reactivity of Chiral Sesquiterpene Synthons Obtained by the Degradation of Maslinic Acid from Olive‐Pressing Residues

  摘要：

  Maslinic acid, a naturally occurring compound isolated from the solid wastes of olive-oil pressing, was fragmented through the C-ring via oxidative procedures to obtain two structural fragments. The chemical behaviors of cis-decalin, from the D and E rings, and of trans-decalin fragments, from the A and B rings, were investigated in depth using several chemical and enzymatic reactions. These decalin chiral synthons are interesting intermediates to semisynthesize phenanthrene- and drimane-type compounds and natural tricyclic triterpenes.

  DOI：

  10.1080/00397910600773858
• 作为产物：
  描述：

  methyl (2R,3aS,5aS,9aR,9bS)-2,9b-dihydroxy-3a,8,8-trimethyl-1,2,4,5,6,7,9,9a-octahydrobenzo[e][1]benzofuran-5a-carboxylate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以96%的产率得到(1S,2S,4aS,8aR)-1-(2-hydroxyethyl)-4a-(hydroxymethyl)-2,7,7-trimethyl-3,4,5,6,8,8a-hexahydronaphthalene-1,2-diol
  参考文献：
  名称：

  Reactivity of Chiral Sesquiterpene Synthons Obtained by the Degradation of Maslinic Acid from Olive‐Pressing Residues

  摘要：

  Maslinic acid, a naturally occurring compound isolated from the solid wastes of olive-oil pressing, was fragmented through the C-ring via oxidative procedures to obtain two structural fragments. The chemical behaviors of cis-decalin, from the D and E rings, and of trans-decalin fragments, from the A and B rings, were investigated in depth using several chemical and enzymatic reactions. These decalin chiral synthons are interesting intermediates to semisynthesize phenanthrene- and drimane-type compounds and natural tricyclic triterpenes.

  DOI：

  10.1080/00397910600773858