(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 | 188752-08-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (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
• 英文别名: (1R,5R,6S,7R,10R,11S)-5,7-dihydroxy-3,4-di(propan-2-yloxy)tetracyclo[9.3.0.01,5.06,10]tetradec-3-en-2-one
• CAS: 188752-08-1
• 化学式: C₂₀H₃₀O₅
• 分子量: 350.455
• InChiKey: HOXRNZHVLOLJIA-GOSMCVEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.55
• 重原子数：
  25.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  75.99
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3β-acetoxy-5-etienic acid chloride 、 (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 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以91%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 3β-acetoxyandrost-5-ene-17β-carboxylic acid, 9-ester
  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,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