4aβ-Methyl-3,4,4a,5,6,8aα-hexahydronaphthalene-1(2H),7(8H)-dione 7-dimethyl acetal | 87262-04-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4aβ-Methyl-3,4,4a,5,6,8aα-hexahydronaphthalene-1(2H),7(8H)-dione 7-dimethyl acetal
• 英文别名: (4aR,8aR)-7,7-dimethoxy-4a-methyl-3,4,5,6,8,8a-hexahydro-2H-naphthalen-1-one
• CAS: 87262-04-2
• 化学式: C₁₃H₂₂O₃
• 分子量: 226.316
• InChiKey: IPVBYKSKSKUMGQ-CMPLNLGQSA-N

物化性质

• 沸点：
  295.9±30.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.53
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4aβ-Methyl-3,4,4a,5,6,8aα-hexahydronaphthalene-1(2H),7(8H)-dione 7-dimethyl acetal 在 盐酸 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 1.75h， 生成 (4aα,8α,8aβ)-(+/-)-octahydro-8-hydroxy-4a,8-dimethyl-2(1H)-naphthalenone
  参考文献：
  名称：

  Synthesis of all stereoisomers of eudesm-11-en-4-ol. 1. Stereospecific synthesis of the trans- and cis-fused octahydro-8-hydroxy-4a,8-dimethyl-2(1H)-naphthalenones. Conformational analysis of the cis-fused compounds

  摘要：

  An efficient method has been developed for the synthesis of the octahydro-8-hydroxy-4a,8-dimethyl-2-(1H)-naphthalenones 9a-d, which are suitable intermediates in the total synthesis of trans- and cis-fused 1-hydroxyeudesmane sesquiterpenes. Starting from the trans-fused dione 7 the corresponding hydroxy ketones 9a and b could be easily prepared. The cis-fused hydroxy ketones 9c and d were synthesized starting from the dione 8. Protection of the C(7) carbonyl function of 8 as its dimethyl acetal followed by treatment with CH3Li gave the hydroxy ketone 9c. On the other hand, protection of the C(7) carbonyl function of 8 as its ethylene acetal and subsequent treatment with CH3MgI afforded the hydroxy ketone 9d as the main product. NMR studies revealed that 9c exists predominantly in the steroid conformation and that 9d exists exclusively in the nonsteroid conformation.

  DOI：

  10.1021/jo00026a011
• 作为产物：
  描述：

  4A-甲基-4,4a,5,6,7,8-六氢-3H-萘-2-酮 在 硫酸 、 氢溴酸 、 对甲苯磺酸 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 1,4-二氧六环 、 乙醚 为溶剂， 反应 38.5h， 生成 4aβ-Methyl-3,4,4a,5,6,8aα-hexahydronaphthalene-1(2H),7(8H)-dione 7-dimethyl acetal
  参考文献：
  名称：

  Stereospecific synthesis of selectively C-7-acetalized substituted 4a.beta.-methyl-3,4,4a,5,6,8a.alpha.-hexahydronaphthalene-1(2H),7(8H)-diones. A short total synthesis of (.+-.)-.beta.-eudesmol, (.+-.)-.beta.-selinene, and (.+-.)-.beta.-dictyopterol

  摘要：

  DOI：

  10.1021/jo00171a045