ethyl (E)-3-[(2R,3R,6Z,9R)-9-[(1Z)-2-methoxy-3-methylbuta-1,3-dienyl]-3-[(4-methoxyphenyl)methoxy]-7-methyl-2,3,4,5,8,9-hexahydrooxonin-2-yl]prop-2-enoate | 958461-43-3

• 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: ethyl (E)-3-[(2R,3R,6Z,9R)-9-[(1Z)-2-methoxy-3-methylbuta-1,3-dienyl]-3-[(4-methoxyphenyl)methoxy]-7-methyl-2,3,4,5,8,9-hexahydrooxonin-2-yl]prop-2-enoate
• CAS: 958461-43-3
• 化学式: C₂₈H₃₈O₆
• 分子量: 470.606
• InChiKey: PSEFOHAXTAOWRI-PPSYSEICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (2S,3R,6Z,9R)-9-[(1Z)-2-methoxy-3-methylbuta-1,3-dienyl]-3-[(4-methoxyphenyl)methoxy]-7-methyl-2,3,4,5,8,9-hexahydrooxonine-2-carbaldehyde 、 乙氧甲酰基亚甲基三苯基膦 以 甲苯 为溶剂， 以91%的产率得到ethyl (E)-3-[(2R,3R,6Z,9R)-9-[(1Z)-2-methoxy-3-methylbuta-1,3-dienyl]-3-[(4-methoxyphenyl)methoxy]-7-methyl-2,3,4,5,8,9-hexahydrooxonin-2-yl]prop-2-enoate
  参考文献：
  名称：

  An Intramolecular Diels−Alder Strategy for the Asbestinins:  Enantioselective Total Syntheses of 11-Acetoxy-4-deoxyasbestinin D and Asbestinin-12

  摘要：

  [Graphics]The enantioselective total syntheses of 11-acetoxy-4-deoxyasbestinin D and asbestinin-12 have been completed. A glycolate aldol reaction provided a diene useful for ring-closing metathesis to form an oxonene, which was ultimately employed as a template to execute a highly stereoselective intramolecular Diels-Alder cycloaddition, forming the hydroisobenzofuran moiety. The absolute configuration of the asbestinin subclass was confirmed via these synthetic efforts.

  DOI：

  10.1021/jo0712695