(E)-5-(but-3-en-1-yl)-5-(4-(2,4-dichlorophenyl)but-3-en-1-yl)-2,2-dimethyl-1,3-dioxane-4,6-dione | 1350703-91-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (E)-5-(but-3-en-1-yl)-5-(4-(2,4-dichlorophenyl)but-3-en-1-yl)-2,2-dimethyl-1,3-dioxane-4,6-dione
• CAS: 1350703-91-1
• 化学式: C₂₀H₂₂Cl₂O₄
• 分子量: 397.298
• InChiKey: BFZDTQWZBUMERH-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.58
• 重原子数：
  26.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  52.6
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (E)-5-(but-3-en-1-yl)-5-(4-(2,4-dichlorophenyl)but-3-en-1-yl)-2,2-dimethyl-1,3-dioxane-4,6-dione 在 samarium diiodide 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以43%的产率得到rac-(1S,3aS,6R,6aR)-1-(2,4-dichlorobenzyl)-6a-hydroxy-6-methyloctahydropentalene-3a-carboxylic acid
  参考文献：
  名称：

  Radical Cyclization Cascades of Unsaturated Meldrum’s Acid Derivatives

  摘要：

  Unsaturated, differentially substituted Meldrum's acid derivatives undergo cascade cyclizations upon ester reduction with Sml(2)-H2O. The cascade cyclizations proceed in good yield and with high diastereocontrol and convert simple, achiral starting materials to complex molecular architectures, bearing up to four stereocenters, In a single operation. The cascades are triggered by the generation and trapping of unusual radical-anions formed by electron transfer to the ester carbonyl.

  DOI：

  10.1021/ol2029367
• 作为产物：
  描述：

  5-(but-3-enyl)-2,2-dimethyl-1,3-dioxane-4,6-dione 、 (E)-1-(4-bromobut-1-enyl)-2,4-dichlorobenzene 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 96.5h， 以62%的产率得到(E)-5-(but-3-en-1-yl)-5-(4-(2,4-dichlorophenyl)but-3-en-1-yl)-2,2-dimethyl-1,3-dioxane-4,6-dione
  参考文献：
  名称：

  Radical Cyclization Cascades of Unsaturated Meldrum’s Acid Derivatives

  摘要：

  Unsaturated, differentially substituted Meldrum's acid derivatives undergo cascade cyclizations upon ester reduction with Sml(2)-H2O. The cascade cyclizations proceed in good yield and with high diastereocontrol and convert simple, achiral starting materials to complex molecular architectures, bearing up to four stereocenters, In a single operation. The cascades are triggered by the generation and trapping of unusual radical-anions formed by electron transfer to the ester carbonyl.

  DOI：

  10.1021/ol2029367