(-)-(1S,6R)-3-Bromo-8,8-dimethyl-4-oxo-7,9-dioxabicyclo<4.3.0>non-2-ene | 146355-33-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-(1S,6R)-3-Bromo-8,8-dimethyl-4-oxo-7,9-dioxabicyclo<4.3.0>non-2-ene
• 英文别名: (3AR,7AS)-6-Bromo-2,2-dimethyl-3A,7A-dihydro-1,3-benzodioxol-5(4H)-one；(3aR,7aS)-6-bromo-2,2-dimethyl-4,7a-dihydro-3aH-1,3-benzodioxol-5-one
• CAS: 146355-33-1
• 化学式: C₉H₁₁BrO₃
• 分子量: 247.089
• InChiKey: GMFPUAKVPGTSLG-JGVFFNPUSA-N

物化性质

• 沸点：
  319.8±42.0 °C(predicted)
• 密度：
  1.512±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (-)-(1S,6R)-3-Bromo-8,8-dimethyl-4-oxo-7,9-dioxabicyclo<4.3.0>non-2-ene 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 乙醚 为溶剂， 生成 (-)-(E)-(1S,6R)-3-Bromo-8,8-dimethyl-4-propylidene-7,9-dioxabicyclo<4.3.0>non-2-ene
  参考文献：
  名称：

  A stereoselective diene-transmissive [4 + 2]-cycloaddition strategy for the construction of the tetracyclic quassinoid framework

  摘要：

  The tetracyclic quassinoid framework was stereoselectively constructed using a diene-transmissive Diels-Alder reaction between the cyclic formyl-diene 13 and ethyl vinyl ether.

  DOI：

  10.1021/jo00056a008
• 作为产物：
  描述：

  (4S,5R)-4,5-O-isopropylidenedioxycyclohex-2-en-1-one 在 溴 、 三乙胺 作用下， 以 四氯化碳 为溶剂， 生成 (-)-(1S,6R)-3-Bromo-8,8-dimethyl-4-oxo-7,9-dioxabicyclo<4.3.0>non-2-ene
  参考文献：
  名称：

  The Diene-Transmissive [4 + 2]-Cycloaddition Strategy: Stereoselective Synthesis of Advanced Intermediates to Quassinoids

  摘要：

  Complex intermediates to quassinoids', some optically active and containing many functional groups, were synthesized via a diene-transmissive Diels-Alder strategy. The stereochemistry of the key inter- and intramolecular cycloadditions was controlled by stereodefined groups on the preexisting C ring and on the tether.

  DOI：

  10.1021/jo00098a017

文献信息

• A stereoselective diene-transmissive [4 + 2]-cycloaddition strategy for the construction of the tetracyclic quassinoid framework
  作者：Claude Spino、Gang Liu

  DOI：10.1021/jo00056a008

  日期：1993.2

  The tetracyclic quassinoid framework was stereoselectively constructed using a diene-transmissive Diels-Alder reaction between the cyclic formyl-diene 13 and ethyl vinyl ether.
• The Diene-Transmissive [4 + 2]-Cycloaddition Strategy: Stereoselective Synthesis of Advanced Intermediates to Quassinoids
  作者：Claude Spino、Gang Liu、Noah Tu、Suzanne Girard

  DOI：10.1021/jo00098a017

  日期：1994.9

  Complex intermediates to quassinoids', some optically active and containing many functional groups, were synthesized via a diene-transmissive Diels-Alder strategy. The stereochemistry of the key inter- and intramolecular cycloadditions was controlled by stereodefined groups on the preexisting C ring and on the tether.
• 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.