8-Hydroxy-5-methoxy-8-((3aS,5S,7aS)-5-methyl-2-triisopropylsilanyloxy-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyran-7-yl)-bicyclo[4.2.0]octa-1(6),2,4-trien-7-one | 1061364-18-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃吡喃类
• 英文名称: 8-Hydroxy-5-methoxy-8-((3aS,5S,7aS)-5-methyl-2-triisopropylsilanyloxy-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyran-7-yl)-bicyclo[4.2.0]octa-1(6),2,4-trien-7-one
• 英文别名: 8-[(3aS,5S,7aS)-5-methyl-2-tri(propan-2-yl)silyloxy-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyran-7-yl]-8-hydroxy-5-methoxybicyclo[4.2.0]octa-1(6),2,4-trien-7-one
• CAS: 1061364-18-8
• 化学式: C₂₆H₃₈O₆Si
• 分子量: 474.67
• InChiKey: QYFQOMNVDKWWAA-JRFDMLTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  三甲基氯硅烷 、 8-Hydroxy-5-methoxy-8-((3aS,5S,7aS)-5-methyl-2-triisopropylsilanyloxy-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyran-7-yl)-bicyclo[4.2.0]octa-1(6),2,4-trien-7-one 生成 5-Methoxy-8-((3aS,5S,7aS)-5-methyl-2-triisopropylsilanyloxy-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyran-7-yl)-8-trimethylsilanyloxy-bicyclo[4.2.0]octa-1(6),2,4-trien-7-one
  参考文献：
  名称：

  General Enantiospecific Route to Isochromanquinones. Synthesis of (-)-Nanaomycin D

  摘要：

  A general enantiospecific synthesis of isochromanquinones is presented. This entails an efficient synthesis of (3aS, 5S, 7aR)-7-bromo-3,3a,5,7a-tetrahydro-5-methyl-2H-furo[3,2-b]pyran-2-one (12) and ultimately the lithium agent 15 from commercially available L-rhamnose. Addition of 15 to the appropriate cyclobutenedione followed by thermolysis of the resulting cyclobutenone leads to the isochromanquinones 16a-c. In an analogous fashion the naturally occurring product, (-)-nanaomycin D, was synthesized. In addition, new methodology involving the ring expansion of iminocyclobutenones to aminophenols was discovered.

  DOI：

  10.1021/jo00104a004
• 作为产物：
  描述：

  ((2S,5R,6S)-4-Bromo-5-hydroxy-6-methyl-5,6-dihydro-2H-pyran-2-yl)-acetic acid methyl ester 在 2,6-二甲基吡啶 、 lithium hydroxide 、 叔丁基锂 、 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 乙醚 、 苯 为溶剂， 生成 8-Hydroxy-5-methoxy-8-((3aS,5S,7aS)-5-methyl-2-triisopropylsilanyloxy-3,3a,5,7a-tetrahydro-2H-furo[3,2-b]pyran-7-yl)-bicyclo[4.2.0]octa-1(6),2,4-trien-7-one
  参考文献：
  名称：

  General Enantiospecific Route to Isochromanquinones. Synthesis of (-)-Nanaomycin D

  摘要：

  A general enantiospecific synthesis of isochromanquinones is presented. This entails an efficient synthesis of (3aS, 5S, 7aR)-7-bromo-3,3a,5,7a-tetrahydro-5-methyl-2H-furo[3,2-b]pyran-2-one (12) and ultimately the lithium agent 15 from commercially available L-rhamnose. Addition of 15 to the appropriate cyclobutenedione followed by thermolysis of the resulting cyclobutenone leads to the isochromanquinones 16a-c. In an analogous fashion the naturally occurring product, (-)-nanaomycin D, was synthesized. In addition, new methodology involving the ring expansion of iminocyclobutenones to aminophenols was discovered.

  DOI：

  10.1021/jo00104a004