[(1aR,3aS,7aS,7bR)-1a,4,4,7a-tetramethyl-2,3,3a,5,6,7-hexahydronaphtho[1,2-b]oxiren-7b-yl]-[4,5-dimethoxy-2-(oxan-2-yloxy)phenyl]methanol | 1225495-64-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(1aR,3aS,7aS,7bR)-1a,4,4,7a-tetramethyl-2,3,3a,5,6,7-hexahydronaphtho[1,2-b]oxiren-7b-yl]-[4,5-dimethoxy-2-(oxan-2-yloxy)phenyl]methanol
• CAS: 1225495-64-6
• 化学式: C₂₈H₄₂O₆
• 分子量: 474.638
• InChiKey: CEQDTOKUFIUAHH-IDXCLQTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  69.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [(1aR,3aS,7aS,7bR)-1a,4,4,7a-tetramethyl-2,3,3a,5,6,7-hexahydronaphtho[1,2-b]oxiren-7b-yl]-[4,5-dimethoxy-2-(oxan-2-yloxy)phenyl]methanol 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 生成 (1R,2R,4aS,8aS)-1-[[4,5-dimethoxy-2-(oxan-2-yloxy)phenyl]-hydroxymethyl]-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydro-2H-naphthalen-1-ol
  参考文献：
  名称：

  Enantiospecific, Biosynthetically Inspired Formal Total Synthesis of (+)-Liphagal

  摘要：

  A biosynthetically inspired synthesis of (+)-liphagal has been achieved from (+)-sclareolide in 13 steps (9% overall yield). The key step is a biomimetic ring expansion of a highly stabilized benzylic carbocation, which generates the seven-membered ring and the benzofuran of the natural product in a single cascade reaction.

  DOI：

  10.1021/ol100756z
• 作为产物：
  描述：

  (1aR,3aS,7aS,7bs)-1a,4,4,7a-tetramethyl-decahydronaphtho[2,1-b]oxirene-7b-carbaldehyde 、 2-(2-bromo-4,5-dimethoxyphenoxy)tetrahydro-2H-pyran 在 叔丁基锂 、 水 、 氯化铵 作用下， 以 四氢呋喃 、 正戊烷 为溶剂， 反应 1.17h， 以94%的产率得到[(1aR,3aS,7aS,7bR)-1a,4,4,7a-tetramethyl-2,3,3a,5,6,7-hexahydronaphtho[1,2-b]oxiren-7b-yl]-[4,5-dimethoxy-2-(oxan-2-yloxy)phenyl]methanol
  参考文献：
  名称：

  Enantiospecific, Biosynthetically Inspired Formal Total Synthesis of (+)-Liphagal

  摘要：

  A biosynthetically inspired synthesis of (+)-liphagal has been achieved from (+)-sclareolide in 13 steps (9% overall yield). The key step is a biomimetic ring expansion of a highly stabilized benzylic carbocation, which generates the seven-membered ring and the benzofuran of the natural product in a single cascade reaction.

  DOI：

  10.1021/ol100756z

文献信息

• Enantiospecific, Biosynthetically Inspired Formal Total Synthesis of (+)-Liphagal
  作者：Jonathan H. George、Jack E. Baldwin、Robert M. Adlington

  DOI：10.1021/ol100756z

  日期：2010.5.21

  A biosynthetically inspired synthesis of (+)-liphagal has been achieved from (+)-sclareolide in 13 steps (9% overall yield). The key step is a biomimetic ring expansion of a highly stabilized benzylic carbocation, which generates the seven-membered ring and the benzofuran of the natural product in a single cascade reaction.