(3S,5R)-1-bromo-3,5-dimethoxycyclopentene | 188752-19-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,5R)-1-bromo-3,5-dimethoxycyclopentene
• CAS: 188752-19-4
• 化学式: C₇H₁₁BrO₂
• 分子量: 207.067
• InChiKey: AGAJNLLEYFOIPH-IYSWYEEDSA-N

物化性质

• 沸点：
  228.0±40.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  2

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 、 (3S,5R)-1-bromo-3,5-dimethoxycyclopentene 生成 (3aR,6aS,6bR,7S,9bR)-4,5,6,6a,6b,7,8,9b-octahydro-9b-hydroxy-1,2-diisopropoxy-7-methoxy-3H-dicyclopenta[a,b]pentalen-3-one 、 (3aS,6aR,6bS,7S,9bS)-4,5,6,6a,6b,7,8,9b-octahydro-9b-hydroxy-1,2-diisopropoxy-7-methoxy-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：

  ((1S,4R)-3-Bromo-4-methoxy-cyclopent-2-enyloxy)-tert-butyl-dimethyl-silane 在 四丁基氟化铵 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 生成 (3S,5R)-1-bromo-3,5-dimethoxycyclopentene
  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

• Danikiewicz, Witold; Jaworski, Tadeusz; Kwiatkowski, Stefan, Synthetic Communications, 1983, vol. 13, # 3, p. 255 - 264
  作者：Danikiewicz, Witold、Jaworski, Tadeusz、Kwiatkowski, Stefan

  DOI：——

  日期：——
• DANIKIEWICZ, W.;JAWORSKI, T.;KWIATKOWSKI, S., SYNTH. COMMUN., 1983, 13, N 3, 255-264
  作者：DANIKIEWICZ, W.、JAWORSKI, T.、KWIATKOWSKI, S.

  DOI：——

  日期：——