(3a'R,6'R,7a'S)-6'-ethyl-5,5-dimethylhexahydrospiro[1,3-dioxane-2,1'-indene]-5'(4'H)-one | 1131429-96-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3a'R,6'R,7a'S)-6'-ethyl-5,5-dimethylhexahydrospiro[1,3-dioxane-2,1'-indene]-5'(4'H)-one
• 英文别名: (3'aR,6'R,7'aS)-6'-ethyl-5,5-dimethylspiro[1,3-dioxane-2,1'-3,3a,4,6,7,7a-hexahydro-2H-indene]-5'-one
• CAS: 1131429-96-3
• 化学式: C₁₆H₂₆O₃
• 分子量: 266.381
• InChiKey: JKYKQLCGDGEEIE-UPJWGTAASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3a'R,6'R,7a'S)-6'-ethyl-5,5-dimethylhexahydrospiro[1,3-dioxane-2,1'-indene]-5'(4'H)-one 、 碳酸二甲酯 在 sodium hydride 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 3.42h， 生成
  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：

  (3a'R,7a'R)-6'-ethyl-5,5-dimethyl-2',3',3a',7a'-tetrahydrospiro[1,3-dioxane-2,1'-indene]-5'(4'H)-one 在 5%-palladium/activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以95%的产率得到(3a'R,6'R,7a'S)-6'-ethyl-5,5-dimethylhexahydrospiro[1,3-dioxane-2,1'-indene]-5'(4'H)-one
  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

文献信息

• Synthesis of (+)-Coronafacic Acid
  作者：Douglass F. Taber、Ritesh B. Sheth、Weiwei Tian

  DOI：10.1021/jo802493k

  日期：2009.3.20

  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.