1-[3,3-Dimethyl-2-(2,4,6-trimethylbenzoyl)-1,2-oxazolidin-5-yl]-5-methylpyrimidine-2,4-dione | 1416969-48-6

• 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: 1-[3,3-Dimethyl-2-(2,4,6-trimethylbenzoyl)-1,2-oxazolidin-5-yl]-5-methylpyrimidine-2,4-dione
• 英文别名: 1-[3,3-dimethyl-2-(2,4,6-trimethylbenzoyl)-1,2-oxazolidin-5-yl]-5-methylpyrimidine-2,4-dione
• CAS: 1416969-48-6
• 化学式: C₂₀H₂₅N₃O₄
• 分子量: 371.436
• InChiKey: ORPNVMLVGLCFRY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  79
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2,4,6-trimethylbenzaldehyde oxime 在 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 、 溴 、 N-甲基吗啉氧化物 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 1-[3,3-Dimethyl-2-(2,4,6-trimethylbenzoyl)-1,2-oxazolidin-5-yl]-5-methylpyrimidine-2,4-dione
  参考文献：
  名称：

  N,O-Nucleosides from Ene Reactions of Nitrosocarbonyl Intermediates with the 3-Methyl-2-buten-1-ol

  摘要：

  Nitrosocarbonyl intermediates undergo ene reactions with allylic alcohols, affording regioisomeric adducts in fair yields. Nitrosocarbonyl benzene reacts with 3-methyl-2-buten-1-ol and follows a Markovnikov orientation and abstracts preferentially the twix hydrogens over the lone ones. With the more sterically demanding nitrosocarbonyl mesitylene and anthracene, the Markovnikov directing effect is relieved and lone abstraction is observed, affording the 5-hydroxy-isoxazolidines that serve as synthons for the preparation of N,O-nucleoside analogues according to the Vorbruggen protocol.

  DOI：

  10.1021/jo302346a

文献信息

• <i>N</i>,<i>O</i>-Nucleosides from Ene Reactions of Nitrosocarbonyl Intermediates with the 3-Methyl-2-buten-1-ol
  作者：Paolo Quadrelli、Mariella Mella、Serena Carosso、Bruna Bovio

  DOI：10.1021/jo302346a

  日期：2013.1.18

  Nitrosocarbonyl intermediates undergo ene reactions with allylic alcohols, affording regioisomeric adducts in fair yields. Nitrosocarbonyl benzene reacts with 3-methyl-2-buten-1-ol and follows a Markovnikov orientation and abstracts preferentially the twix hydrogens over the lone ones. With the more sterically demanding nitrosocarbonyl mesitylene and anthracene, the Markovnikov directing effect is relieved and lone abstraction is observed, affording the 5-hydroxy-isoxazolidines that serve as synthons for the preparation of N,O-nucleoside analogues according to the Vorbruggen protocol.