(4R,5R)-2,8-dimethyl-4-(methoxymethoxy)-5-(pivaloyloxy)-bicyclo[5.3.0]deca-1,7-dien-9-one | 1006369-93-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4R,5R)-2,8-dimethyl-4-(methoxymethoxy)-5-(pivaloyloxy)-bicyclo[5.3.0]deca-1,7-dien-9-one
• 英文别名: [(5R,6R)-6-(methoxymethoxy)-3,8-dimethyl-2-oxo-4,5,6,7-tetrahydro-1H-azulen-5-yl] 2,2-dimethylpropanoate
• CAS: 1006369-93-2
• 化学式: C₁₉H₂₈O₅
• 分子量: 336.428
• InChiKey: LYHYRXSLUVQJIG-IAGOWNOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4R,5R)-2,8-dimethyl-4-(methoxymethoxy)-5-(pivaloyloxy)-bicyclo[5.3.0]deca-1,7-dien-9-one 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Total Synthesis of (+)-Achalensolide Based on the Rh(I)-Catalyzed Allenic Pauson−Khand-Type Reaction

  摘要：

  [GRAPHICS]The first total synthesis of (+)-achalensolide was achieved from a commercially available D-(-)-isoascorbic acid. The known epoxide, derived from D-(-)-isoascorbic acid, was converted into the allenyne, the Rh(I)-catalyzed Pauson-Khand-type reaction of which directly provided the bicyclo[5.3.0]decane system, a core framework of the title natural product. The construction of the gamma-lactone moiety and some chemical modifications resulted in the completion of the total synthesis of (+)-achalensolide.

  DOI：

  10.1021/jo702330y
• 作为产物：
  描述：

  (5R,6R)-3-methyl-5-(methoxymethoxy)-6-(pivaloyloxy)deca-1,2-dien-8-yne 、 一氧化碳 在 chloro(1,5-cyclooctadiene)rhodium(I) dimer 、 1,3-双(二苯基膦)丙烷 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以96%的产率得到(4R,5R)-2,8-dimethyl-4-(methoxymethoxy)-5-(pivaloyloxy)-bicyclo[5.3.0]deca-1,7-dien-9-one
  参考文献：
  名称：

  Total Synthesis of (+)-Achalensolide Based on the Rh(I)-Catalyzed Allenic Pauson−Khand-Type Reaction

  摘要：

  [GRAPHICS]The first total synthesis of (+)-achalensolide was achieved from a commercially available D-(-)-isoascorbic acid. The known epoxide, derived from D-(-)-isoascorbic acid, was converted into the allenyne, the Rh(I)-catalyzed Pauson-Khand-type reaction of which directly provided the bicyclo[5.3.0]decane system, a core framework of the title natural product. The construction of the gamma-lactone moiety and some chemical modifications resulted in the completion of the total synthesis of (+)-achalensolide.

  DOI：

  10.1021/jo702330y