5-(cyclohex-2-enyl)-1,3-dimethyl-6-hydroxyuracil | 954367-57-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 5-(cyclohex-2-enyl)-1,3-dimethyl-6-hydroxyuracil
• 英文别名: 5-cyclohex-2-en-1-yl-6-hydroxy-1,3-dimethylpyrimidine-2,4-dione
• CAS: 954367-57-8
• 化学式: C₁₂H₁₆N₂O₃
• 分子量: 236.271
• InChiKey: LKZRTANPFOAJST-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  60.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(cyclohex-2-enyl)-1,3-dimethyl-6-hydroxyuracil 在 溴 作用下， 以 氯仿 为溶剂， 反应 6.0h， 以50%的产率得到(4bRS,8RS,8aRS)-8-bromo-1,3-dimethyl-4b,5,6,7,8,8a-hexahydro-1H-benzo[4.5]furo[2,3-d]pyrimidine-2,4-dione
  参考文献：
  名称：

  Synthesis of Pyrimidine-Annelated Heterocycles: Regioselective Heterocyclization of 5-(Cyclohex-2-enyl)-1,3-dimethyl-6-hydroxyuracil [1]

  摘要：

  5-(Cyclohex-2-enyl)-1,3-dimethyl-6-hydroxyuracil undergoes regioselective heterocyclization to afford fused tricyclic heterocycles upon treatment with bromine and m-CPBA. However, the same substrate furnished bridged tricyclic heterocycles when treated with N-iodosuccinimide and cone. H2SO4 and a mixture of bridged tricyclic heterocycles and fused tricyclic heterocycles when treated with hexamine hydrotribromide or pyridine hydrotribromide.

  DOI：

  10.1007/s007060200088
• 作为产物：
  描述：

  1,3-二甲基巴比妥酸 、 3-溴环己烯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 6.0h， 以60%的产率得到5-(cyclohex-2-enyl)-1,3-dimethyl-6-hydroxyuracil
  参考文献：
  名称：

  Synthesis of Pyrimidine-Annelated Heterocycles: Regioselective Heterocyclization of 5-(Cyclohex-2-enyl)-1,3-dimethyl-6-hydroxyuracil [1]

  摘要：

  5-(Cyclohex-2-enyl)-1,3-dimethyl-6-hydroxyuracil undergoes regioselective heterocyclization to afford fused tricyclic heterocycles upon treatment with bromine and m-CPBA. However, the same substrate furnished bridged tricyclic heterocycles when treated with N-iodosuccinimide and cone. H2SO4 and a mixture of bridged tricyclic heterocycles and fused tricyclic heterocycles when treated with hexamine hydrotribromide or pyridine hydrotribromide.

  DOI：

  10.1007/s007060200088

文献信息

• Stannic Chloride–Iodine: An Efficient Reagent for Regioselective Synthesis of Furan–Fused Heterocycles
  作者：K. C. Majumdar、A. Biswas、P. P. Mukhopadhyay

  DOI：10.1080/00397910701470982

  日期：2007.8.1

  SnCl4-I-2-mediated cyclization of ortho-cyclohexenyl phenol and ortho-cyclohexenyl enol derivatives of coumarin, uracil, dimedone, and pyrone at room temperature for 1 h give the linear cyclized products in 78-90% yield, which, on treatment with 10% Pd-C at 250 degrees C for 1-2 h, afford corresponding aromatized products in 80-84% yield.