(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 | 1225495-51-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: (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
• CAS: 1225495-51-1
• 化学式: C₂₈H₄₄O₆
• 分子量: 476.654
• InChiKey: CKHYDUWYBQAWFX-CULLHWFUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (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 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以110 mg的产率得到(2S,7S,10R)-15,16-dimethoxy-2,6,6,10-tetramethyl-12-oxatetracyclo[9.7.0.02,7.013,18]octadeca-1(11),13,15,17-tetraene
  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,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