5,5-Bis(2-hydroperoxy-2,2-diphenylethyl)-1,3-dimethylbarbituric acid | 150058-67-6

• 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: 5,5-Bis(2-hydroperoxy-2,2-diphenylethyl)-1,3-dimethylbarbituric acid
• 英文别名: 5,5-bis(2-hydroperoxy-2,2-diphenylethyl)-1,3-dimethyl-1,3-diazinane-2,4,6-trione
• CAS: 150058-67-6
• 化学式: C₃₄H₃₂N₂O₇
• 分子量: 580.637
• InChiKey: LTKACDMGWLYHLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.67
• 重原子数：
  43.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  116.61
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  5,5-Bis(2-hydroperoxy-2,2-diphenylethyl)-1,3-dimethylbarbituric acid 在 溶剂黄146 、 锌 作用下， 反应 1.0h， 以96%的产率得到5,5-Bis(2-hydroxy-2,2-diphenylethyl)-1,3-dimethylbarbituric acid
  参考文献：
  名称：

  Manganese(II) acetate-mediated double 2-hydroperoxyalkylations of barbituric acid and its derivatives

  摘要：

  The reactions of 1,1-disubstituted ethenes with barbituric acid and its derivatives in the presence of manganese(II) acetate and air yielded 5,5-bis(2-hydroperoxyalkyl)barbituric acids 3aa-ac and 3ba-ja in 62-99% yields. The structure of 3ab was determined by X-ray crystallography. The reaction of la and 2a was also effected by manganese(III) acetate (95%) and metallic manganese (92%), but in poor yield by cerium(IV) ammonium nitrate (50%). Treatment of 5,5-bis(2-hydroperoxy-2,2-diphenylethyl)-1,3-dimethylbarbituric acid(3aa) with perchloric acid gave 5,5-bis(benzoylmethyl)-1,3-dimethylbarbituric acid (6) and 5-(2-benzoylmethyl)-1,3-dimethyl-5-(2,2-diphenylethenyl)-barbituric acid (7), in which phenyl migration took place. Reduction of 3aa with zinc powder in acetic acid or with triphenylphosphine in diethyl ether yielded 5,5-bis(2-hydroxy-2,2-diphenylethyl)-1,3-dimethylbarbituric acid (10), which was dehydrated to give a spirotetrahydropyran 11.

  DOI：

  10.1021/jo00068a046
• 作为产物：
  描述：

  1,1-二苯乙烯 、 1,3-二甲基巴比妥酸 在 air 、 manganese(II) acetate 作用下， 以 溶剂黄146 为溶剂， 反应 5.0h， 以96%的产率得到5,5-Bis(2-hydroperoxy-2,2-diphenylethyl)-1,3-dimethylbarbituric acid
  参考文献：
  名称：

  Manganese(II) acetate-mediated double 2-hydroperoxyalkylations of barbituric acid and its derivatives

  摘要：

  The reactions of 1,1-disubstituted ethenes with barbituric acid and its derivatives in the presence of manganese(II) acetate and air yielded 5,5-bis(2-hydroperoxyalkyl)barbituric acids 3aa-ac and 3ba-ja in 62-99% yields. The structure of 3ab was determined by X-ray crystallography. The reaction of la and 2a was also effected by manganese(III) acetate (95%) and metallic manganese (92%), but in poor yield by cerium(IV) ammonium nitrate (50%). Treatment of 5,5-bis(2-hydroperoxy-2,2-diphenylethyl)-1,3-dimethylbarbituric acid(3aa) with perchloric acid gave 5,5-bis(benzoylmethyl)-1,3-dimethylbarbituric acid (6) and 5-(2-benzoylmethyl)-1,3-dimethyl-5-(2,2-diphenylethenyl)-barbituric acid (7), in which phenyl migration took place. Reduction of 3aa with zinc powder in acetic acid or with triphenylphosphine in diethyl ether yielded 5,5-bis(2-hydroxy-2,2-diphenylethyl)-1,3-dimethylbarbituric acid (10), which was dehydrated to give a spirotetrahydropyran 11.

  DOI：

  10.1021/jo00068a046