(1R,2S,6S,7R,8R,10S)-10-hydroxy-6-isopropenyl-3-methoxy-4,13-dimethyl-15-oxatricyclo[6.6.1.0^2,7]pentadeca-3,12-dien-9-one | 958461-45-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: (1R,2S,6S,7R,8R,10S)-10-hydroxy-6-isopropenyl-3-methoxy-4,13-dimethyl-15-oxatricyclo[6.6.1.0^2,7]pentadeca-3,12-dien-9-one
• 英文别名: (1R,2S,6S,7R,8R,10S,12Z)-10-hydroxy-3-methoxy-4,13-dimethyl-6-prop-1-en-2-yl-15-oxatricyclo[6.6.1.02,7]pentadeca-3,12-dien-9-one
• CAS: 958461-45-5
• 化学式: C₂₀H₂₈O₄
• 分子量: 332.44
• InChiKey: PHMUDQPGGAMLBO-ZQWYPGDASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2S,6S,7R,8R,10S)-10-hydroxy-6-isopropenyl-3-methoxy-4,13-dimethyl-15-oxatricyclo[6.6.1.0^2,7]pentadeca-3,12-dien-9-one 、 甲基氯化镁 以 四氢呋喃 为溶剂， 反应 0.5h， 以83%的产率得到(1R,2S,6S,7R,8R,9R,10S)-6-isopropenyl-3-methoxy-4,9,13-trimethyl-15-oxatricyclo[6.6.1.0^2,7]pentadeca-3,12-diene-9,10-diol
  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
• 作为产物：
  描述：

  (1R,2S,6S,7R,8R)-6-isopropenyl-3-methoxy-4,13-dimethyl-15-oxatricyclo[6.6.6.0^2,7]pentadeca-3,12-dien-9-one 在 双(三甲基硅烷基)氨基钾 、 (+)-8,8-二氯樟脑磺哑嗪 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.75h， 生成 (1R,2S,6S,7R,8R,10S)-10-hydroxy-6-isopropenyl-3-methoxy-4,13-dimethyl-15-oxatricyclo[6.6.1.0^2,7]pentadeca-3,12-dien-9-one
  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

文献信息

• An Intramolecular Diels−Alder Strategy for the Asbestinins:  Enantioselective Total Syntheses of 11-Acetoxy-4-deoxyasbestinin D and Asbestinin-12
  作者：Michael T. Crimmins、J. Michael Ellis

  DOI：10.1021/jo0712695

  日期：2008.3.1

  [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.