[(3S,3aR,3bS,6aS,7aS)-3b-hydroxy-6a-methyl-6-oxo-4,5-di(propan-2-yloxy)-1,2,3,3a,7,7a-hexahydrocyclopenta[a]pentalen-3-yl] (2R)-2-methoxy-2-phenylacetate | 188752-16-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: [(3S,3aR,3bS,6aS,7aS)-3b-hydroxy-6a-methyl-6-oxo-4,5-di(propan-2-yloxy)-1,2,3,3a,7,7a-hexahydrocyclopenta[a]pentalen-3-yl] (2R)-2-methoxy-2-phenylacetate
• CAS: 188752-16-1
• 化学式: C₂₇H₃₆O₇
• 分子量: 472.579
• InChiKey: QGGXLROVTCGVLG-NRLJPGDMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  34.0
• 可旋转键数：
  8.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  91.29
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  [(3S,3aR,3bS,6aS,7aS)-3b-hydroxy-6a-methyl-6-oxo-4,5-di(propan-2-yloxy)-1,2,3,3a,7,7a-hexahydrocyclopenta[a]pentalen-3-yl] (2R)-2-methoxy-2-phenylacetate 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 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：

  (3aS,3bS,6aS,7aS)-3a-Hydroxy-2,3-diisopropoxy-7a-methyl-3b,5,6,6a,7,7a-hexahydro-3aH-cyclopenta[a]pentalene-1,4-dione 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 [(3S,3aR,3bS,6aS,7aS)-3b-hydroxy-6a-methyl-6-oxo-4,5-di(propan-2-yloxy)-1,2,3,3a,7,7a-hexahydrocyclopenta[a]pentalen-3-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