(1S,5R)-1-[(1Z)-but-1-en-1-yl]-5',5'-dimethylspiro[bicyclo[3.1.0]hexane-2,2'-[1,3]dioxane] | 1131429-81-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,5R)-1-[(1Z)-but-1-en-1-yl]-5',5'-dimethylspiro[bicyclo[3.1.0]hexane-2,2'-[1,3]dioxane]
• 英文别名: (1'S,5'R)-1'-[(Z)-but-1-enyl]-5,5-dimethylspiro[1,3-dioxane-2,2'-bicyclo[3.1.0]hexane]
• CAS: 1131429-81-6
• 化学式: C₁₅H₂₄O₂
• 分子量: 236.354
• InChiKey: VWANDRCYJWWLCM-QZWGFMDZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  一氧化碳 、 (1S,5R)-1-[(1Z)-but-1-en-1-yl]-5',5'-dimethylspiro[bicyclo[3.1.0]hexane-2,2'-[1,3]dioxane] 在 iron pentacarbonyl 、 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 异丙醇 为溶剂， 反应 5.0h， 以90 mg的产率得到(3a'R,7a'R)-6'-ethyl-5,5-dimethyl-2',3',3a',7a'-tetrahydrospiro[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
• 作为产物：
  描述：

  propylidenetriphenylphosphorane 、 (1S,5R)-5',5'-dimethyl-1H-spiro[bicyclo[3.1.0]hexane-2,2'-[1,3]dioxane]-1-carbaldehyde 以 四氢呋喃 为溶剂， 反应 1.0h， 以78%的产率得到(1S,5R)-1-[(1Z)-but-1-en-1-yl]-5',5'-dimethylspiro[bicyclo[3.1.0]hexane-2,2'-[1,3]dioxane]
  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.