(3aR,5R,7aS)-6-bromo-3a,4,5,7a-tetrahydro-5-methoxy-2,2-dimethyl-1,3-benzodioxole | 188752-23-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,5R,7aS)-6-bromo-3a,4,5,7a-tetrahydro-5-methoxy-2,2-dimethyl-1,3-benzodioxole
• CAS: 188752-23-0
• 化学式: C₁₀H₁₅BrO₃
• 分子量: 263.131
• InChiKey: FSRXLQYDTKPENM-HRDYMLBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  14.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

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 、 (3aR,5R,7aS)-6-bromo-3a,4,5,7a-tetrahydro-5-methoxy-2,2-dimethyl-1,3-benzodioxole 在 叔丁基锂 作用下， 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 、 (4R)-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
• 作为产物：
  描述：

  (-)-(1S,6R)-3-Bromo-8,8-dimethyl-4-oxo-7,9-dioxabicyclo<4.3.0>non-2-ene 在 sodium tetrahydroborate 、 cerium(III) chloride 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 0.25h， 生成 (3aR,5R,7aS)-6-bromo-3a,4,5,7a-tetrahydro-5-methoxy-2,2-dimethyl-1,3-benzodioxole
  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