4-(hepta-4,6-dienyl)-5-(tertbutyldimethylsilyloxy)-2,2-dimethyl-4H-[1.3]dioxin | 379717-31-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(hepta-4,6-dienyl)-5-(tertbutyldimethylsilyloxy)-2,2-dimethyl-4H-[1.3]dioxin
• 英文别名: tert-butyl-[[4-[(4E)-hepta-4,6-dienyl]-2,2-dimethyl-4H-1,3-dioxin-5-yl]oxy]-dimethylsilane
• CAS: 379717-31-4
• 化学式: C₁₉H₃₄O₃Si
• 分子量: 338.563
• InChiKey: OTBGGXDCWZXVAC-ZHACJKMWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.91
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(hepta-4,6-dienyl)-5-(tertbutyldimethylsilyloxy)-2,2-dimethyl-4H-[1.3]dioxin 在 二甲基氯化铝 作用下， 以 正己烷 、 二氯甲烷 为溶剂， 反应 12.0h， 生成 5-(tert-butyldimethylsilyloxy)-2,3,3a,5,6,8a-hexahydro-1H-azulen-4-one 、
  参考文献：
  名称：

  Stereoselective Preparation of (Z)-2-(Trialkylsilyloxy)-2-alkenals by Retrocycloaddition Reactions of 4H-4-Alkyl-5-(trialkylsilyloxy)-1,3-dioxins. Useful Reactants for Lewis Acid Catalyzed [4 + 3] Cyclizations

  摘要：

  [GRAPHICS]Retrocycloadditions of 4H-4-alkyl-5-(trialylsilyloxy)-1,3-dioxins proceed smoothly in refluxing toluene to afford (Z)-2-(trialkylsilyloxy)-2-alkenals with complete stereos electivity. These enals undergo Sasaki-type [4 + 3] cyclizations with dienes in the presence of Lewis acids, in many instances with excellent regio- and/or stereoselectivity.

  DOI：

  10.1021/ol016668f
• 作为产物：
  描述：

  (E)-1-iodohepta-4,6-diene 在 正丁基锂 、 sodium hexamethyldisilazane 、 二乙胺 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 6.0h， 生成 4-(hepta-4,6-dienyl)-5-(tertbutyldimethylsilyloxy)-2,2-dimethyl-4H-[1.3]dioxin
  参考文献：
  名称：

  Stereoselective Preparation of (Z)-2-(Trialkylsilyloxy)-2-alkenals by Retrocycloaddition Reactions of 4H-4-Alkyl-5-(trialkylsilyloxy)-1,3-dioxins. Useful Reactants for Lewis Acid Catalyzed [4 + 3] Cyclizations

  摘要：

  [GRAPHICS]Retrocycloadditions of 4H-4-alkyl-5-(trialylsilyloxy)-1,3-dioxins proceed smoothly in refluxing toluene to afford (Z)-2-(trialkylsilyloxy)-2-alkenals with complete stereos electivity. These enals undergo Sasaki-type [4 + 3] cyclizations with dienes in the presence of Lewis acids, in many instances with excellent regio- and/or stereoselectivity.

  DOI：

  10.1021/ol016668f

文献信息

• Stereoselective Preparation of (<i>Z</i>)-2-(Trialkylsilyloxy)-2-alkenals by Retrocycloaddition Reactions of 4<i>H</i>-4-Alkyl-5-(trialkylsilyloxy)-1,3-dioxins. Useful Reactants for Lewis Acid Catalyzed [4 + 3] Cyclizations
  作者：Ronald A. Aungst、Raymond L. Funk

  DOI：10.1021/ol016668f

  日期：2001.11.1

  [GRAPHICS]Retrocycloadditions of 4H-4-alkyl-5-(trialylsilyloxy)-1,3-dioxins proceed smoothly in refluxing toluene to afford (Z)-2-(trialkylsilyloxy)-2-alkenals with complete stereos electivity. These enals undergo Sasaki-type [4 + 3] cyclizations with dienes in the presence of Lewis acids, in many instances with excellent regio- and/or stereoselectivity.