5-benzyl-5-(cyclohex-2-enyl)-2,2-dimethyl-1,3-dioxane-4,6-dione

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-benzyl-5-(cyclohex-2-enyl)-2,2-dimethyl-1,3-dioxane-4,6-dione
• 英文别名: 5-Benzyl-5-cyclohex-2-en-1-yl-2,2-dimethyl-1,3-dioxane-4,6-dione
• 化学式: C₁₉H₂₂O₄
• 分子量: 314.381
• InChiKey: PTPXUHZIELQEFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,2-二甲基-5-(苯基甲基)-1,3-二噁烷-4,6-二酮 、 2-环己烯醇 在 四(三苯基膦)钯 、 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以73%的产率得到5-benzyl-5-(cyclohex-2-enyl)-2,2-dimethyl-1,3-dioxane-4,6-dione
  参考文献：
  名称：

  Mitsunobu C-Alkylation of Meldrum's Acids

  摘要：

  C-Dialkylation of Meldrum's acid (2a) and 5-benzyl Meldrum's acid (2b) can be achieved through Mitsunobu dehydration using allylic and arylmethyl alcohols as alkylating agents. This is the first time that the Mitsunobu reaction is successfully applied to the C-alkylation of a highly enolizable cyclic beta-dicarbonyl system. With primary (allylic and arylmethyl) alcohols, the alkylations always take place at the carbon bearing the hydroxy: group. For secondary allylic alcohols, a catalytic amount of Pd(0) must be added to enhance the regioselectivity of C-alkylation over O-alkylation. With (Ph(3)P)(4)Pd(0) as a catalyst, the reaction occurs specifically at the less hindered carbon, and the configuration of the resultant double bond is always trans. Attempts to monoalkylate Meldrum's acids 2a and 2b failed.

  DOI：

  10.1021/jo962288+

文献信息

• Mitsunobu <i>C</i>-Alkylation of Meldrum's Acids
  作者：Tony K. M. Shing、Lian-Hai Li、Kesavaram Narkunan

  DOI：10.1021/jo962288+

  日期：1997.3.1

  C-Dialkylation of Meldrum's acid (2a) and 5-benzyl Meldrum's acid (2b) can be achieved through Mitsunobu dehydration using allylic and arylmethyl alcohols as alkylating agents. This is the first time that the Mitsunobu reaction is successfully applied to the C-alkylation of a highly enolizable cyclic beta-dicarbonyl system. With primary (allylic and arylmethyl) alcohols, the alkylations always take place at the carbon bearing the hydroxy: group. For secondary allylic alcohols, a catalytic amount of Pd(0) must be added to enhance the regioselectivity of C-alkylation over O-alkylation. With (Ph(3)P)(4)Pd(0) as a catalyst, the reaction occurs specifically at the less hindered carbon, and the configuration of the resultant double bond is always trans. Attempts to monoalkylate Meldrum's acids 2a and 2b failed.