(4S)-4-[(3aS,6R,7aR)-6-methoxy-2,2-dimethyl-3a,6,7,7a-tetrahydro-1,3-benzodioxol-5-yl]-4-hydroxy-2,3-di(propan-2-yloxy)cyclobut-2-en-1-one | 188752-29-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S)-4-[(3aS,6R,7aR)-6-methoxy-2,2-dimethyl-3a,6,7,7a-tetrahydro-1,3-benzodioxol-5-yl]-4-hydroxy-2,3-di(propan-2-yloxy)cyclobut-2-en-1-one
• CAS: 188752-29-6
• 化学式: C₂₀H₃₀O₇
• 分子量: 382.454
• InChiKey: OGTZBLMXZPYEGL-IGMJJTELSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.23
• 重原子数：
  27.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  83.45
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-碘环戊烯 、 (4S)-4-[(3aS,6R,7aR)-6-methoxy-2,2-dimethyl-3a,6,7,7a-tetrahydro-1,3-benzodioxol-5-yl]-4-hydroxy-2,3-di(propan-2-yloxy)cyclobut-2-en-1-one 在 叔丁基锂 作用下， 生成 (3aR,6aS,6bR,7S,8R,10bR)-5,6,6a,6b,7,8,9,10b-octahydro-10b-hydroxy-1,2-diisopropoxy-7,8-(isopropylidenedioxy)dicyclopent[a,b]inden-3(4H)-one 、 (3aS,6aR,6bR,7S,8R,10bS)-5,6,6a,6b,7,8,9,10b-octahydro-10b-hydroxy-1,2-diisopropoxy-7,8-(isopropylidenedioxy)dicyclopent[a,b]inden-3(4H)-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：

  (4S,5R)-4,5-O-isopropylidenedioxycyclohex-2-en-1-one 在 sodium tetrahydroborate 、 cerium(III) chloride 、 溴 、 叔丁基锂 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.33h， 生成 (4S)-4-[(3aS,6R,7aR)-6-methoxy-2,2-dimethyl-3a,6,7,7a-tetrahydro-1,3-benzodioxol-5-yl]-4-hydroxy-2,3-di(propan-2-yloxy)cyclobut-2-en-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