(1R,2S,4S,6S,7R,8R,9R,10S)-9,10-dihydroxy-6-isopropenyl-4,9,13-trimethyl-15-oxatricyclo[6.6.1.0^2,7]pentadec-12-en-3-one | 958461-48-8

• 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,4S,6S,7R,8R,9R,10S)-9,10-dihydroxy-6-isopropenyl-4,9,13-trimethyl-15-oxatricyclo[6.6.1.0^2,7]pentadec-12-en-3-one
• 英文别名: (1R,2S,4S,6S,7R,8R,9R,10S,12Z)-9,10-dihydroxy-4,9,13-trimethyl-6-prop-1-en-2-yl-15-oxatricyclo[6.6.1.02,7]pentadec-12-en-3-one
• CAS: 958461-48-8
• 化学式: C₂₀H₃₀O₄
• 分子量: 334.456
• InChiKey: IQDZVGWIQCBJNF-KLEASPNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  24
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2S,4S,6S,7R,8R,9R,10S)-9,10-dihydroxy-6-isopropenyl-4,9,13-trimethyl-15-oxatricyclo[6.6.1.0^2,7]pentadec-12-en-3-one 在 L-Selectride 作用下， 以 四氢呋喃 为溶剂， 反应 0.17h， 以94%的产率得到(1R,2R,3S,4S,6S,7R,8R,9R,10S)-6-isopropenyl-4,9,13-trimethyl-15-oxatricyclo[6.6.1.0^2,7]pentadec-12-ene-3,9,10-triol
  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,4R,6S,7R,8R,9R,10S)-9,10-dihydroxy-6-isopropenyl-4,9,13-trimethyl-15-oxatricyclo[6.6.1.0^2,7]pentadec-12-en-3-one 在 甲醇 、 sodium hydride 作用下， 反应 0.25h， 以42%的产率得到(1R,2S,4S,6S,7R,8R,9R,10S)-9,10-dihydroxy-6-isopropenyl-4,9,13-trimethyl-15-oxatricyclo[6.6.1.0^2,7]pentadec-12-en-3-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.