(3aR,4aS,5R,6S,8aS,9aR)-2,2,4a,6,9,9-hexamethyl-4,5,7,8,8a,9a-hexahydro-3aH-naphtho[6,7-d][1,3]dioxole-5,6-diol | 918437-03-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,4aS,5R,6S,8aS,9aR)-2,2,4a,6,9,9-hexamethyl-4,5,7,8,8a,9a-hexahydro-3aH-naphtho[6,7-d][1,3]dioxole-5,6-diol
• CAS: 918437-03-3
• 化学式: C₁₇H₃₀O₄
• 分子量: 298.423
• InChiKey: SHVSFQPLNUVLNK-VRCYMCHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3aR,4aS,5R,6S,8aS,9aR)-2,2,4a,6,9,9-hexamethyl-4,5,7,8,8a,9a-hexahydro-3aH-naphtho[6,7-d][1,3]dioxole-5,6-diol 在 sodium periodate 作用下， 以 水 、 丙酮 为溶剂， 反应 12.0h， 以70%的产率得到(3aR,5S,6S,7aR)-2,2,5,7,7-pentamethyl-6-(3-oxobutyl)-3a,4,6,7a-tetrahydro-1,3-benzodioxole-5-carbaldehyde
  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：

  [(2R,3R,4aS,7R,8aS)-3-acetyloxy-4,4,8a-trimethyl-8-oxospiro[1,2,3,4a,5,6-hexahydronaphthalene-7,2'-oxirane]-2-yl] acetate 在 lithium aluminium tetrahydride 、 4-甲基苯磺酸丙酯 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 (3aR,4aS,5R,6S,8aS,9aR)-2,2,4a,6,9,9-hexamethyl-4,5,7,8,8a,9a-hexahydro-3aH-naphtho[6,7-d][1,3]dioxole-5,6-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