8-hydroxymethyl-4',4'-dimethyl-2-methylsulfanyl-3,4,5,6,7,8-hexahydropyrido[2,3-d]pyrimidine-6-spiro-1'-cyclohexane-2',4,6'-trione | 749234-58-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 英文名称: 8-hydroxymethyl-4',4'-dimethyl-2-methylsulfanyl-3,4,5,6,7,8-hexahydropyrido[2,3-d]pyrimidine-6-spiro-1'-cyclohexane-2',4,6'-trione
• 英文别名: 8-Hydroxymethyl-4',4'-dimethyl-2-methylsulfanyl-3,4,5,6,7,8-hexahydropyrido[2,3-d]pyrimidine-6-spiro-1'-cyclohexane-2',4,6'-trione；8-(hydroxymethyl)-5',5'-dimethyl-2-methylsulfanylspiro[5,7-dihydro-3H-pyrido[2,3-d]pyrimidine-6,2'-cyclohexane]-1',3',4-trione
• CAS: 749234-58-0
• 化学式: C₁₆H₂₁N₃O₄S
• 分子量: 351.426
• InChiKey: SXLVEOUELAIORA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  124
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  乙醇 、 8-hydroxymethyl-4',4'-dimethyl-2-methylsulfanyl-3,4,5,6,7,8-hexahydropyrido[2,3-d]pyrimidine-6-spiro-1'-cyclohexane-2',4,6'-trione 反应 0.25h， 以55%的产率得到8-(ethoxymethyl)-5',5'-dimethyl-2-methylsulfanylspiro[5,7-dihydro-3H-pyrido[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：

  基巯基-4-氨基-6-羟基嘧啶 在 三乙胺 作用下， 以 乙醇 、 水 为溶剂， 反应 0.03h， 生成 8-hydroxymethyl-4',4'-dimethyl-2-methylsulfanyl-3,4,5,6,7,8-hexahydropyrido[2,3-d]pyrimidine-6-spiro-1'-cyclohexane-2',4,6'-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

文献信息

• Three hexahydropyridopyrimidine-spiro-cyclohexanetriones: supramolecular structures generated by O—H...O, N—H...O, C—H...O and C—H...π hydrogen bonds, and π–π stacking interactions
  作者：John N. Low、George Ferguson、Justo Cobo、Manuel Nogueras、Silvia Cruz、Jairo Quiroga、Christopher Glidewell

  DOI：10.1107/s0108270104009539

  日期：2004.6.15

  4',4'-Dimethyl-2-methylsulfanyl-3,4,5,6,7,8-hexahydropyrido-[2,3-d] pyrimidine-6-spiro-1'-cyclohexane-2',4,6'-trione, C15H19N3O3S, (I), has a markedly polarized molecular-electronic structure, and the molecules are linked into a three-dimensional framework by a combination of N-H...O, C-H...O and C-H...pi hydrogen bonds. 8-Hydroxymethyl-4',4'-dimethyl-2-methylsulfanyl-3,4,5,6,7,8-hexahydropyrido[2,3-d] pyrimidine-6-spiro-1'-cyclohexane-2',4,6'-trione, C16H21N3O4S, (II), where the hydroxymethyl substituent is disordered over two sets of sites, has a much less polarized structure than (I); the molecules are linked by a combination of O-H...O and N-H...O hydrogen bonds into chains containing alternating R-2(2)(8) and R-2(2)(16) rings, and these chains are linked into sheets by a combination of a pi-pi stacking interaction and a C-H...O hydrogen bond. 8-Ethoxymethyl-2-methoxy-4',4'-dimethyl-3,4,5,6,7,8-hexahydropyrido-[2,3-d]-pyrimidine-6-spiro-1'-cyclohexane-2',4,6'-trione, C18H25N3O5, (III), has an unpolarized electronic structure, and a combination of N-H...O, C-H...O and C-H...pi hydrogen bonds links the molecules into sheets.