(3AR,5S,7AS)-6-Bromo-2,2-dimethyl-3A,4,5,7A-tetrahydro-1,3-benzodioxol-5-OL | 188752-36-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3AR,5S,7AS)-6-Bromo-2,2-dimethyl-3A,4,5,7A-tetrahydro-1,3-benzodioxol-5-OL
• 英文别名: (3aR,5S,7aS)-6-bromo-2,2-dimethyl-3a,4,5,7a-tetrahydro-1,3-benzodioxol-5-ol
• CAS: 188752-36-5
• 化学式: C₉H₁₃BrO₃
• 分子量: 249.104
• InChiKey: KBUBYZGDPQPDAU-BIIVOSGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3AR,5S,7AS)-6-Bromo-2,2-dimethyl-3A,4,5,7A-tetrahydro-1,3-benzodioxol-5-OL 在 叔丁基锂 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 14.0h， 生成 (4R)-4-[(3aS,6S,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：

  (4S,5R)-4,5-O-isopropylidenedioxycyclohex-2-en-1-one 在 sodium tetrahydroborate 、 cerium(III) chloride 、 溴 、 三乙胺 作用下， 以 甲醇 为溶剂， 反应 0.33h， 生成 (3AR,5S,7AS)-6-Bromo-2,2-dimethyl-3A,4,5,7A-tetrahydro-1,3-benzodioxol-5-OL
  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

文献信息

• Enhanced Channeling of the Squarate Cascade through the Dianionic Oxy-Cope Option. Oxy Substitution Markedly Augments Syn Delivery of the Second Alkenyllithium
  作者：Leo A. Paquette、Lung Huang Kuo、Julien Doyon

  DOI：10.1021/ja964140d

  日期：1997.4.1

  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.