(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 | 875431-99-5

• 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: (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
• 英文别名: (3R,3aS,6R,8R,10Z,12aS)-3-hydroxy-8-(methoxymethoxy)-6,10,12a-trimethyl-1,2,3,3a,5,6,7,8,9,12-decahydrocyclopenta[11]annulen-4-one
• CAS: 875431-99-5
• 化学式: C₁₉H₃₂O₄
• 分子量: 324.461
• InChiKey: CZPDQHIQRBDIEB-RPIYGOHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (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 在 溶剂黄146 、 tetramethylammonium triacetoxyborohydride 作用下， 以 乙腈 为溶剂， 以70%的产率得到(Z)-(1R,3aS,8R,10S,12S,12aS)-8-Methoxymethoxy-3a,6,10-trimethyl-1,2,3,3a,4,7,8,9,10,11,12,12a-dodecahydro-cyclopentacycloundecene-1,12-diol
  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)-(1R,2S,4S,6R,11S,14R)-6-Methoxymethoxy-4,8,11-trimethyl-15-oxa-tricyclo[12.1.0.0^1,11]pentadec-8-en-2-ol 在 lithium tetrafluoroborate 作用下， 以 乙腈 为溶剂， 以100%的产率得到(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