(4aα,8aα)-(+/-)-hexahydro-4a-methyl-1(2H),7(8H)-naphthalenedione | 87332-36-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4aα,8aα)-(+/-)-hexahydro-4a-methyl-1(2H),7(8H)-naphthalenedione
• 英文别名: 4aβ-Methyl-3,4,4a,5,6,8aα-hexahydronaphthalene-1(2H),7(8H)-dione；4abeta-Methyl-3,4,4a,5,6,7,8aalpha-hexahydronaphthalene-1(2H),7(8H)-dione；(4aR,8aR)-4a-methyl-3,4,5,6,8,8a-hexahydro-2H-naphthalene-1,7-dione
• CAS: 87332-36-3
• 化学式: C₁₁H₁₆O₂
• 分子量: 180.247
• InChiKey: PQTSRSJNADEALT-GXSJLCMTSA-N

物化性质

• 沸点：
  295.9±23.0 °C(Predicted)
• 密度：
  1.084±0.06 g/cm3(Predicted)
• 保留指数：
  1927

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  (4aα,8aα)-(+/-)-hexahydro-4a-methyl-1(2H),7(8H)-naphthalenedione 在 对甲苯磺酸 4-甲基苯磺酸吡啶 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 121.0h， 生成 (4aα,8aα)-(+/-)-octahydro-7,7-dimethoxy-4a-methyl-1(2H)-napthalenone
  参考文献：
  名称：

  A new route to selectively protected cis 4a-methyl-hexahydronaphthalene-1(2H), 7(8H)-diones

  摘要：

  DOI：

  10.1016/s0040-4039(00)84544-x
• 作为产物：
  描述：

  8β-Hydroxy-4aβ-methyl-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one 在 三氯化钛 、 pyridinium chlorochromate 作用下， 以 盐酸 、 丙酮 、 苯 为溶剂， 反应 21.0h， 生成 (4aα,8aα)-(+/-)-hexahydro-4a-methyl-1(2H),7(8H)-naphthalenedione
  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

文献信息

• Microbial hydroxylation and functionalization of synthetic polycyclic enones
  作者：Abderrahmane Hammoumi、Jean-Pierre Girault、Robert Azerad、Gilbert Revial、Jean d'Angelo

  DOI：10.1016/s0957-4166(00)80241-4

  日期：1993.6

  The regio- and stereoselective hydroxylation of variously substituted asymmetric 4a-methyl octalenones by selected fungal strains has been shown to afford, sometimes in high yields, several optically pure derivatives, generally hydroxylated in the B-ring. The potential of this method for the preparation of functionalized (hydroxylated) chiral synthons is evaluated and discussed.
• 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
  作者：Ronald P. W. Kesselmans、Joannes B. P. A. Wijnberg、Aede De Groot、Nanne K. De Vries

  DOI：10.1021/jo00026a011

  日期：1991.12

  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.