(2R,3R)-6-bromo-2,3-dimethyl-1,4-dioxaspiro[4.4]non-6-ene | 188752-33-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: (2R,3R)-6-bromo-2,3-dimethyl-1,4-dioxaspiro[4.4]non-6-ene
• CAS: 188752-33-2
• 化学式: C₉H₁₃BrO₂
• 分子量: 233.105
• InChiKey: ZCDJKJNHZWRWHY-RNFRBKRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.58
• 重原子数：
  12.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  18.46
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3,4-二异丙氧基-3-环丁烯-1,2-二酮 、 1-碘环戊烯 、 (2R,3R)-6-bromo-2,3-dimethyl-1,4-dioxaspiro[4.4]non-6-ene 生成 (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 、 (3aS,6aR,6bS,9bS)-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
  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：

  (2R,3R)-(-)-2,3-丁二醇 、 2-溴-2-环戊酮 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 反应 48.0h， 以69%的产率得到(2R,3R)-6-bromo-2,3-dimethyl-1,4-dioxaspiro[4.4]non-6-ene
  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