4-amino-5-(2-hydroxy-4,4-dimethyl-6-oxocyclohexenylmethyl)-1-methyl-2-(methylsulfanyl)pyrimidin-6(1H)-one | 709036-74-8

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-amino-5-(2-hydroxy-4,4-dimethyl-6-oxocyclohexenylmethyl)-1-methyl-2-(methylsulfanyl)pyrimidin-6(1H)-one
• 英文别名: 4-Amino-1-methyl-5-(2-hydroxy-4,4-dimethyl-2-oxocyclohexenylmethyl)-2-(methylsulfanyl)pyrimidin-6(1H)-one；6-amino-5-[(2-hydroxy-4,4-dimethyl-6-oxocyclohexen-1-yl)methyl]-3-methyl-2-methylsulfanylpyrimidin-4-one
• CAS: 709036-74-8
• 化学式: C₁₅H₂₁N₃O₃S
• 分子量: 323.416
• InChiKey: UWQUQXZYVYEQMQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  121
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-amino-5-(2-hydroxy-4,4-dimethyl-6-oxocyclohexenylmethyl)-1-methyl-2-(methylsulfanyl)pyrimidin-6(1H)-one 反应 4.25h， 生成 8-(Methoxymethyl)-3,5',5'-trimethyl-2-methylsulfanylspiro[5,7-dihydropyrido[2,3-d]pyrimidine-6,2'-cyclohexane]-1',3',4-trione
  参考文献：
  名称：

  Three-component synthesis of hexahydropyridopyrimidine–spirocyclohexanetriones induced by microwave

  摘要：

  Pyridopyrimidine-spirocyclohexanetriones (5, 6) and pyrimido[4,5-b]quinolinones (8) were obtained in a three-component microwave-assisted reaction of 6-aminopyrimidin-4-ones (1) with dimedone (2) and formaldehyde solution or paraformaldehyde, respectively. A mechanism is proposed based on the presence of a basic catalyst (triethylamine in this case) and the fact that single condensation intermediates are isolated prior to the cyclization leading to the final products. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.10.120
• 作为产物：
  描述：

  3-hydroxy-2-[(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)methyl]-5,5-dimethylcyclohex-2-en-1-one 、 6-氨基-2-甲基硫代-3-甲基尿嘧啶 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 0.03h， 生成 4-amino-5-(2-hydroxy-4,4-dimethyl-6-oxocyclohexenylmethyl)-1-methyl-2-(methylsulfanyl)pyrimidin-6(1H)-one
  参考文献：
  名称：

  Three-component synthesis of hexahydropyridopyrimidine–spirocyclohexanetriones induced by microwave

  摘要：

  Pyridopyrimidine-spirocyclohexanetriones (5, 6) and pyrimido[4,5-b]quinolinones (8) were obtained in a three-component microwave-assisted reaction of 6-aminopyrimidin-4-ones (1) with dimedone (2) and formaldehyde solution or paraformaldehyde, respectively. A mechanism is proposed based on the presence of a basic catalyst (triethylamine in this case) and the fact that single condensation intermediates are isolated prior to the cyclization leading to the final products. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.10.120

文献信息

• 4-Amino-5-(2-hydroxy-4,4-dimethyl-6-oxocyclohexenylmethyl)-1-methyl-2-(methylsulfanyl)pyrimidin-6(1<i>H</i>)-one: hydrogen-bonded chains are π-stacked in pairs
  作者：John N. Low、Justo Cobo、Silvia Cruz、Jairo Quiroga、Christopher Glidewell

  DOI：10.1107/s0108270104001118

  日期：2004.3.15

  Molecules of the title compound, C15H21N3O3S, have a markedly polarized electronic structure; the carbocyclic ring adopts an envelope conformation and the overall molecular conformation appears to be controlled by two intramolecular hydrogen bonds, one each of the O-H...O and N-H...O types. The molecules are linked into C(6) chains by an intermolecular N-H...O hydrogen bond, and pairs of these hydrogen-bonded chains are linked by a pi-pi stacking interaction.
• Three-component synthesis of hexahydropyridopyrimidine–spirocyclohexanetriones induced by microwave
  作者：Jairo Quiroga、Silvia Cruz、Braulio Insuasty、Rodrigo Abonía、Manuel Nogueras、Justo Cobo

  DOI：10.1016/j.tetlet.2005.10.120

  日期：2006.1

  Pyridopyrimidine-spirocyclohexanetriones (5, 6) and pyrimido[4,5-b]quinolinones (8) were obtained in a three-component microwave-assisted reaction of 6-aminopyrimidin-4-ones (1) with dimedone (2) and formaldehyde solution or paraformaldehyde, respectively. A mechanism is proposed based on the presence of a basic catalyst (triethylamine in this case) and the fact that single condensation intermediates are isolated prior to the cyclization leading to the final products. (c) 2005 Elsevier Ltd. All rights reserved.