(6α,6aα,8β,10β,10aβ)-6-ethyl-2,6,6a,7,8,9,10,10a-octahydro-2-hydroxy-6a,8,10-trimethyl-1H-[2]benzopyrano[4,3-c]pyridin-1-one | 184031-21-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (6α,6aα,8β,10β,10aβ)-6-ethyl-2,6,6a,7,8,9,10,10a-octahydro-2-hydroxy-6a,8,10-trimethyl-1H-[2]benzopyrano[4,3-c]pyridin-1-one
• 英文别名: fusaricide；(6R,6aS,8S,10R,10aS)-6-ethyl-2-hydroxy-6a,8,10-trimethyl-6,7,8,9,10,10a-hexahydroisochromeno[4,3-c]pyridin-1-one
• CAS: 184031-21-8
• 化学式: C₁₇H₂₅NO₃
• 分子量: 291.39
• InChiKey: KRTBGHXNQMTBCL-MRYGCYLCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (4bS,5R,7S,8aS,9R)-9-Ethyl-5,7,8a-trimethyl-3-trimethylsilanyloxy-3,4b,5,6,7,8,8a,9-octahydro-10-oxa-3-aza-phenanthren-4-one 在 韦德伊斯试剂 、 ethylene diamine tetraacetic acid tetrasodium salt 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 10.5h， 以3.6 mg的产率得到(6α,6aα,8β,10β,10aβ)-6-ethyl-2,6,6a,7,8,9,10,10a-octahydro-2-hydroxy-6a,8,10-trimethyl-1H-[2]benzopyrano[4,3-c]pyridin-1-one
  参考文献：
  名称：

  TOTAL SYNTHESIS OF (±)-FUSARICIDE

  摘要：

  Condensation of pyridone 6 with enal 25 using DMAP in EtOH at 150 degreesC afforded 8% of the desired Diels-Alder adduct 22, 8% of the bridged adduct 36 and 1-2% of a partially pure cis-fused adduct 37 of unknown stereochemistry. Hydroxylation of 22 completed a short synthesis of fusaricide (1).

  DOI：

  10.1081/scc-100105395

文献信息

• TOTAL SYNTHESIS OF (±)-FUSARICIDE
  作者：Barry B. Snider、Rachel. B. Smith

  DOI：10.1081/scc-100105395

  日期：2001.1.1

  Condensation of pyridone 6 with enal 25 using DMAP in EtOH at 150 degreesC afforded 8% of the desired Diels-Alder adduct 22, 8% of the bridged adduct 36 and 1-2% of a partially pure cis-fused adduct 37 of unknown stereochemistry. Hydroxylation of 22 completed a short synthesis of fusaricide (1).