(Z)-(4S,6S,8R,12aS)-8-Methoxymethoxy-6,10,12a-trimethyl-1,2,4,5,6,7,8,9,12,12a-decahydro-cyclopentacycloundecen-4-ol | 875431-96-2

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (Z)-(4S,6S,8R,12aS)-8-Methoxymethoxy-6,10,12a-trimethyl-1,2,4,5,6,7,8,9,12,12a-decahydro-cyclopentacycloundecen-4-ol
• 英文别名: (4S,6S,8R,10Z,12aS)-8-(methoxymethoxy)-6,10,12a-trimethyl-2,4,5,6,7,8,9,12-octahydro-1H-cyclopenta[11]annulen-4-ol
• CAS: 875431-96-2
• 化学式: C₁₉H₃₂O₃
• 分子量: 308.461
• InChiKey: VQRFWWQAJKTTOJ-FVLFCEINSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (Z)-(4S,6S,8R,12aS)-8-Methoxymethoxy-6,10,12a-trimethyl-1,2,4,5,6,7,8,9,12,12a-decahydro-cyclopentacycloundecen-4-ol 在 叔丁基过氧化氢 、 lithium tetrafluoroborate 、 bis(acetylacetonate)oxovanadium 作用下， 以 乙腈 、 苯 为溶剂， 生成 (Z)-(3R,3aS,6R,8R,12aS)-3-Hydroxy-8-methoxymethoxy-6,10,12a-trimethyl-2,3,3a,5,6,7,8,9,12,12a-decahydro-1H-cyclopentacycloundecen-4-one
  参考文献：
  名称：

  Stereospecific rearrangement of α-hydroxyepoxide: efficient approach to the trans-bicyclo[9.3.0]tetradecane core en route to clavulactone

  摘要：

  We document a synthetic route to trans-bicyclo[9.3.0]tetradecanes. The strategy is based oil a quantitative and stereospecific Lewis acid mediated rearrangement of alpha-hydroxyepoxide to beta-hydroxyketone, which paved the way for the synthesis of clavulactone and clavirolides. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.11.021
• 作为产物：
  描述：

  (Z)-(6R,8R,12aS)-8-Methoxymethoxy-6,10,12a-trimethyl-2,5,6,7,8,9,12,12a-octahydro-1H-cyclopentacycloundecen-4-one 在 二异丁基氢化铝 作用下， 以76%的产率得到(Z)-(4S,6S,8R,12aS)-8-Methoxymethoxy-6,10,12a-trimethyl-1,2,4,5,6,7,8,9,12,12a-decahydro-cyclopentacycloundecen-4-ol
  参考文献：
  名称：

  Stereospecific rearrangement of α-hydroxyepoxide: efficient approach to the trans-bicyclo[9.3.0]tetradecane core en route to clavulactone

  摘要：

  We document a synthetic route to trans-bicyclo[9.3.0]tetradecanes. The strategy is based oil a quantitative and stereospecific Lewis acid mediated rearrangement of alpha-hydroxyepoxide to beta-hydroxyketone, which paved the way for the synthesis of clavulactone and clavirolides. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.11.021