5-methyl-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidin-4-one | 885109-44-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并嘧啶类
• 英文名称: 5-methyl-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidin-4-one
• CAS: 885109-44-4
• 化学式: C₇H₈N₄OS
• 分子量: 196.233
• InChiKey: DAXSBPBJJAYGJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  86.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-methyl-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidin-4-one 在 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.0h， 生成 1-(4-methoxy-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3-(6-methoxy-5-methyl-4-oxo-1,5-dihydropyrazolo[3,4-d]pyrimidin-1-yl)propane
  参考文献：
  名称：

  Design and synthesis of pyrazolo[3,4-d]pyrimidine core based dissymmetrical ‘Leonard linker’ compounds: 1H NMR and crystallographic evidence for folded conformation due to arene interactions

  摘要：

  Proton NMR analysis of two newly synthesized 'Leonard/trimethylene linker' dissymmetrical compounds 1-(4,6-dimethylsulfanyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3-(5-methyl-6-methylsulfanyl-4-oxo-1,5-dihydropyrazolo[3,4-d]pyrimidin-1-yl)propane (8) and 1-(4-methoxy-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3-(6-methoxy-5-methyl-4-oxo-1,5-dihydropyrazolo[3,4-d]pyrimidin-1-yl)propane (10) show intramolecularly stacked conformation in solution. X-Ray crystallography of dissymmetrical 'Leonard/trimethylene linker' compound (9) based on pyrazolo[3,4-d]pyrimidine core, for the first time, shows unusual U-motif formed due to intramolecular pi-pi stacking interactions, which is similar to earlier related symmetrical compounds 1 & 2. Supramolecular structures of new compound (8) show additional CH...O, CH...N, CH...S and S...S interactions. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2005.10.005
• 作为产物：
  描述：

  6-Methylsulfanyl-1-(tetrahydro-pyran-2-yl)-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one 在 盐酸 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 正戊烷 为溶剂， 反应 16.0h， 生成 5-methyl-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidin-4-one
  参考文献：
  名称：

  Design and synthesis of pyrazolo[3,4-d]pyrimidine core based dissymmetrical ‘Leonard linker’ compounds: 1H NMR and crystallographic evidence for folded conformation due to arene interactions

  摘要：

  Proton NMR analysis of two newly synthesized 'Leonard/trimethylene linker' dissymmetrical compounds 1-(4,6-dimethylsulfanyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3-(5-methyl-6-methylsulfanyl-4-oxo-1,5-dihydropyrazolo[3,4-d]pyrimidin-1-yl)propane (8) and 1-(4-methoxy-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-3-(6-methoxy-5-methyl-4-oxo-1,5-dihydropyrazolo[3,4-d]pyrimidin-1-yl)propane (10) show intramolecularly stacked conformation in solution. X-Ray crystallography of dissymmetrical 'Leonard/trimethylene linker' compound (9) based on pyrazolo[3,4-d]pyrimidine core, for the first time, shows unusual U-motif formed due to intramolecular pi-pi stacking interactions, which is similar to earlier related symmetrical compounds 1 & 2. Supramolecular structures of new compound (8) show additional CH...O, CH...N, CH...S and S...S interactions. (c) 2005 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molstruc.2005.10.005

文献信息

• Conformational control due to arene interactions in dissymmetrical diaryl 2-methylenepropylidene both in solution and solid state
  作者：K. Avasthi、L. Shukla、R. Kant、K. Ravikumar

  DOI：10.1134/s0022476614080289

  日期：2014.12

  We have designed and synthesized dissymmetrical diaryl 2-methylenepropylidenes based on pyrazolo[3,4-d]pyrimidine core for studying conformational control due to arene interactions in face-to-face (offset) mode. Dissymmetrical 2-methylenepropylidene linker models (N-1-N-1 isomers) show intramolecular pi-pi stacking (folded conformation) by H-1 NMR in solution which carries over to solid state as revealed by single crystal X-ray crystallography. Corresponding, N-1-N-2 isomers do not show intramolecular pi-pi stacking at molecular level. In addition to arene interactions crystal structures are also stabilized by intermolecular C-HaEuro broken vertical bar O, C-HaEuro broken vertical bar S or C-HaEuro broken vertical bar N interactions.