methyl (3a'S,6'R,7a'S)-6'-ethyl-5,5-dimethyl-2',3',3a',6',7',7a'-hexahydrospiro[1,3-dioxane-2,1'-indene]-4'-carboxylate | 1131430-00-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (3a'S,6'R,7a'S)-6'-ethyl-5,5-dimethyl-2',3',3a',6',7',7a'-hexahydrospiro[1,3-dioxane-2,1'-indene]-4'-carboxylate
• 英文别名: methyl (3'aS,6'R,7'aS)-6'-ethyl-5,5-dimethylspiro[1,3-dioxane-2,1'-2,3,3a,6,7,7a-hexahydroindene]-4'-carboxylate
• CAS: 1131430-00-6
• 化学式: C₁₈H₂₈O₄
• 分子量: 308.418
• InChiKey: YOGGPDWRDOABJC-GUTXKFCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (3a'S,6'R,7a'S)-6'-ethyl-5,5-dimethyl-2',3',3a',6',7',7a'-hexahydrospiro[1,3-dioxane-2,1'-indene]-4'-carboxylate 在 盐酸 、 水 作用下， 反应 4.0h， 以55%的产率得到(+)-coronafacic acid
  参考文献：
  名称：

  Synthesis of (+)-Coronafacic Acid

  摘要：

  An enantioselective synthesis of (+)-coronafacic acid has been achieved. Rhodium-catalyzed cyclization of an alpha-diazoester provided the intermediate cyclopentanone in high enantiomeric purity. Subsequent Fe-mediated cyclocarbonylation of a derived alkenyl cyclopropane gave a bicyclic enone that then was hydrogenated and carried on to the natural product.

  DOI：

  10.1021/jo802493k
• 作为产物：
  描述：

  在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以56%的产率得到methyl (3a'S,6'R,7a'S)-6'-ethyl-5,5-dimethyl-2',3',3a',6',7',7a'-hexahydrospiro[1,3-dioxane-2,1'-indene]-4'-carboxylate
  参考文献：
  名称：

  Synthesis of (+)-Coronafacic Acid

  摘要：

  An enantioselective synthesis of (+)-coronafacic acid has been achieved. Rhodium-catalyzed cyclization of an alpha-diazoester provided the intermediate cyclopentanone in high enantiomeric purity. Subsequent Fe-mediated cyclocarbonylation of a derived alkenyl cyclopropane gave a bicyclic enone that then was hydrogenated and carried on to the natural product.

  DOI：

  10.1021/jo802493k