(3aR,6aS,6bR,9aR,9bR)-5,6,6b,7,8,9a,9b-octahydro-9b-hydroxy-1,2-diisopropoxy-3H-dicyclopenta[a,b]pentalene-3,9(4H)-dione | 188752-06-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,6aS,6bR,9aR,9bR)-5,6,6b,7,8,9a,9b-octahydro-9b-hydroxy-1,2-diisopropoxy-3H-dicyclopenta[a,b]pentalene-3,9(4H)-dione
• 英文别名: (1R,5R,6R,10R,11S)-5-hydroxy-3,4-di(propan-2-yloxy)tetracyclo[9.3.0.01,5.06,10]tetradec-3-ene-2,7-dione
• CAS: 188752-06-9
• 化学式: C₂₀H₂₈O₅
• 分子量: 348.439
• InChiKey: PDXYWSZRNUMZPP-WOPBUMQYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aR,6aS,6bR,9aR,9bR)-5,6,6b,7,8,9a,9b-octahydro-9b-hydroxy-1,2-diisopropoxy-3H-dicyclopenta[a,b]pentalene-3,9(4H)-dione 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 以77%的产率得到(3aR,6aS,6bR,9R,9aS,9bR)-4,5,6,6a,6b,7,8,9,9a,9b-decahydro-9,9b-dihydroxy-1,2-diisopropoxy-3H-dicyclopenta[a,b]pentalen-3-one
  参考文献：
  名称：

  Enhanced Channeling of the Squarate Cascade through the Dianionic Oxy-Cope Option. Oxy Substitution Markedly Augments Syn Delivery of the Second Alkenyllithium

  摘要：

  A general means for enhancing the extent to which squarate esters enter into cascade processes involving a dianionic oxy-Cope rearrangement as the key step is presented. Adoption of this sigmatropic process requires that the two alkenyllithium reagents being introduced add cis to each other, a kinetic bias which can be realized simply by the proper incorporation of ethereal oxygen substituents in the first organometallic reagent. Structural reorganization occurs via boat-like transition states such that stereoinduction manifests itself with high fidelity.

  DOI：

  10.1021/ja964140d
• 作为产物：
  描述：

  (3aR,6aS,6bR,9bR)-4,5,6,6a,6b,7,7,9b-octahydro-9b-hydroxy-9-((1R,2R)-2-hydroxy-1-methylpropoxy)-1,2-diisopropoxy-3H-dicyclopenta[a,b]pentalen-3-one 在 盐酸 作用下， 以 水 、 丙酮 为溶剂， 反应 24.0h， 以51%的产率得到(3aR,6aS,6bR,9aR,9bR)-5,6,6b,7,8,9a,9b-octahydro-9b-hydroxy-1,2-diisopropoxy-3H-dicyclopenta[a,b]pentalene-3,9(4H)-dione
  参考文献：
  名称：

  Enhanced Channeling of the Squarate Cascade through the Dianionic Oxy-Cope Option. Oxy Substitution Markedly Augments Syn Delivery of the Second Alkenyllithium

  摘要：

  A general means for enhancing the extent to which squarate esters enter into cascade processes involving a dianionic oxy-Cope rearrangement as the key step is presented. Adoption of this sigmatropic process requires that the two alkenyllithium reagents being introduced add cis to each other, a kinetic bias which can be realized simply by the proper incorporation of ethereal oxygen substituents in the first organometallic reagent. Structural reorganization occurs via boat-like transition states such that stereoinduction manifests itself with high fidelity.

  DOI：

  10.1021/ja964140d