(3S,3aS,5aR,9S,9aS,9bS)-3,9-Dimethyl-5a-vinyl-octahydro-furo[2,3-f]isochromene-2,8-dione | 80924-48-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3S,3aS,5aR,9S,9aS,9bS)-3,9-Dimethyl-5a-vinyl-octahydro-furo[2,3-f]isochromene-2,8-dione
• 英文别名: (3S,3aS,5aR,9S,9aS,9bS)-5a-ethenyl-3,9-dimethyl-3,3a,4,5,6,9,9a,9b-octahydrofuro[2,3-f]isochromene-2,8-dione
• CAS: 80924-48-7
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: RXSWGFFXQMMPSD-BIDWDLNYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,3aS,5aR,9S,9aS,9bS)-3,9-Dimethyl-5a-vinyl-octahydro-furo[2,3-f]isochromene-2,8-dione 在 platinum(IV) oxide 氢气 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以50%的产率得到Dihydro-8-deoxytetrahydrovernolepin
  参考文献：
  名称：

  Synthesis of (+)-8-Deoxyvernolepin

  摘要：

  A short and efficient synthesis of (+)-8-deoxyvernolepin (2) from (-)-alpha-santonin (8), by functionalization of the angular methyl from a 2 beta- or 6 beta-alkoxy radical generated by reaction of the alcohol 6 or 7 with diphenylhydroxyselenium acetate and iodine and l,4-fragmentation of the gamma-hydroxystannane 35 using hypervalent organoiodine reagents as the key steps, is described. The most important structural features of this compound and other vernolepin congeners, the delta 8-valerolactone cis-fused to ring B moiety and the angular vinyl group, are introduced in the same step.

  DOI：

  10.1021/jo00100a049
• 作为产物：
  描述：

  山道年 在 Lindlar's catalyst 氢氧化钾 、 sodium tetrahydroborate 、 高氯酸 、 硫酸 、 三氟化硼乙醚 、 氢气 、 双氧水 、 碘 、 potassium carbonate 、 间氯过氧苯甲酸 、 pyridinium chlorochromate 、 mercury(II) oxide 、 zinc(II) iodide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 环己烷 、 异丙醇 、 丙酮 为溶剂， 反应 135.66h， 生成 (3S,3aS,5aR,9S,9aS,9bS)-3,9-Dimethyl-5a-vinyl-octahydro-furo[2,3-f]isochromene-2,8-dione
  参考文献：
  名称：

  Synthesis of (+)-8-Deoxyvernolepin

  摘要：

  A short and efficient synthesis of (+)-8-deoxyvernolepin (2) from (-)-alpha-santonin (8), by functionalization of the angular methyl from a 2 beta- or 6 beta-alkoxy radical generated by reaction of the alcohol 6 or 7 with diphenylhydroxyselenium acetate and iodine and l,4-fragmentation of the gamma-hydroxystannane 35 using hypervalent organoiodine reagents as the key steps, is described. The most important structural features of this compound and other vernolepin congeners, the delta 8-valerolactone cis-fused to ring B moiety and the angular vinyl group, are introduced in the same step.

  DOI：

  10.1021/jo00100a049

文献信息

• Synthesis of (+)-8-Deoxyvernolepin
  作者：Rosendo Hernandez、Silvia M. Velazquez、Ernesto Suarez、Maria S. Rodriguez

  DOI：10.1021/jo00100a049

  日期：1994.10

  A short and efficient synthesis of (+)-8-deoxyvernolepin (2) from (-)-alpha-santonin (8), by functionalization of the angular methyl from a 2 beta- or 6 beta-alkoxy radical generated by reaction of the alcohol 6 or 7 with diphenylhydroxyselenium acetate and iodine and l,4-fragmentation of the gamma-hydroxystannane 35 using hypervalent organoiodine reagents as the key steps, is described. The most important structural features of this compound and other vernolepin congeners, the delta 8-valerolactone cis-fused to ring B moiety and the angular vinyl group, are introduced in the same step.