(E)-2,2-dimethyl-5-(4-phenylbut-3-en-1-yl)-5-(5-phenylpent-4-yn-1-yl)-1,3-dioxane-4,6-dione | 1350703-96-6

• 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)-2,2-dimethyl-5-(4-phenylbut-3-en-1-yl)-5-(5-phenylpent-4-yn-1-yl)-1,3-dioxane-4,6-dione
• 英文别名: 2,2-dimethyl-5-[(E)-4-phenylbut-3-enyl]-5-(5-phenylpent-4-ynyl)-1,3-dioxane-4,6-dione
• CAS: 1350703-96-6
• 化学式: C₂₇H₂₈O₄
• 分子量: 416.517
• InChiKey: CKXWWVAOCDOKMG-YBFXNURJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-2,2-dimethyl-5-(4-phenylbut-3-en-1-yl)-5-(5-phenylpent-4-yn-1-yl)-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， 生成 rac-(1S,3aS,7aS,Z)-1-benzyl-7-benzylidene-7a-hydroxyoctahydro-1H-indene-3a-carboxylic acid 、 rac-(1S,3aS,7aS,E)-1-benzyl-7-benzylidene-7a-hydroxyoctahydro-1H-indene-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-溴戊-1-炔-1-基)苯 在 硫酸 、 水 、 sodium hydride 、 potassium carbonate 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 97.0h， 生成 (E)-2,2-dimethyl-5-(4-phenylbut-3-en-1-yl)-5-(5-phenylpent-4-yn-1-yl)-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

文献信息

• Radical Cyclization Cascades of Unsaturated Meldrum’s Acid Derivatives
  作者：Brice Sautier、Sarah E. Lyons、Michael R. Webb、David J. Procter

  DOI：10.1021/ol2029367

  日期：2012.1.6

  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.