(3aS,6aS,7aS)-4-((1R,2R)-1,2-Dicyclohexyl-2-hydroxy-ethoxy)-3a-hydroxy-2,3-diisopropoxy-7a-methyl-3a,5,6,6a,7,7a-hexahydro-cyclopenta[a]pentalen-1-one | 188752-12-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aS,6aS,7aS)-4-((1R,2R)-1,2-Dicyclohexyl-2-hydroxy-ethoxy)-3a-hydroxy-2,3-diisopropoxy-7a-methyl-3a,5,6,6a,7,7a-hexahydro-cyclopenta[a]pentalen-1-one
• 英文别名: (3bS,6aS,7aS)-3-[(1R,2R)-1,2-dicyclohexyl-2-hydroxyethoxy]-3b-hydroxy-6a-methyl-4,5-di(propan-2-yloxy)-1,2,7,7a-tetrahydrocyclopenta[a]pentalen-6-one
• CAS: 188752-12-7
• 化学式: C₃₂H₅₀O₆
• 分子量: 530.745
• InChiKey: RZPMMOCMSITTJZ-WNAJDOJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.34
• 重原子数：
  38.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  85.22
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (3aS,6aS,7aS)-4-((1R,2R)-1,2-Dicyclohexyl-2-hydroxy-ethoxy)-3a-hydroxy-2,3-diisopropoxy-7a-methyl-3a,5,6,6a,7,7a-hexahydro-cyclopenta[a]pentalen-1-one 在 盐酸 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 50.0h， 生成 [(3S,3aR,3bS,6aS,7aS)-3-hydroxy-6a-methyl-6-oxo-4,5-di(propan-2-yloxy)-1,2,3,3a,7,7a-hexahydrocyclopenta[a]pentalen-3b-yl] (2R)-2-methoxy-2-phenylacetate
  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：

  2-溴丙烯 、 3,4-二异丙氧基-3-环丁烯-1,2-二酮 、 生成 (3aS,6aS,7aS)-4-((1R,2R)-1,2-Dicyclohexyl-2-hydroxy-ethoxy)-3a-hydroxy-2,3-diisopropoxy-7a-methyl-3a,5,6,6a,7,7a-hexahydro-cyclopenta[a]pentalen-1-one 、 (3aR,6aR,7aR)-4-((1R,2R)-1,2-Dicyclohexyl-2-hydroxy-ethoxy)-3a-hydroxy-2,3-diisopropoxy-7a-methyl-3a,5,6,6a,7,7a-hexahydro-cyclopenta[a]pentalen-1-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