1-(3-bromopropyl)-4,6-dimethylsulfanyl-1H-pyrazolo[3,4-d]pyrimidine | 172844-08-5

• 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: 1-(3-bromopropyl)-4,6-dimethylsulfanyl-1H-pyrazolo[3,4-d]pyrimidine
• 英文别名: 1-(3-Bromopropyl)-4,6-bis(methylthio)-1H-pyrazolo[3,4-d]pyrimidine；1-(3-bromopropyl)-4,6-bis(methylsulfanyl)pyrazolo[3,4-d]pyrimidine
• CAS: 172844-08-5
• 化学式: C₁₀H₁₃BrN₄S₂
• 分子量: 333.276
• InChiKey: RITYBAPOKJUYQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  94.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-methyl-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidin-4-one 、 1-(3-bromopropyl)-4,6-dimethylsulfanyl-1H-pyrazolo[3,4-d]pyrimidine 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 以42.5%的产率得到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
  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：

  1,3-二溴丙烷 、 4,6-双(甲基硫代)-1H-吡唑并[3,4-d]嘧啶 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以4%的产率得到1-(3-bromopropyl)-4,6-dimethylsulfanyl-1H-pyrazolo[3,4-d]pyrimidine
  参考文献：
  名称：

  Avasthi, K.; Chandra, T.; Bhakuni, D. S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1995, vol. 34, # 11, p. 944 - 949

  摘要：

  DOI：

文献信息

• Design and synthesis of pyrazolo[3,4-d]pyrimidine and triazolo[4,5-d]pyrimidine based dissymmetrical ‘Leonard linker’ compounds: 1H NMR and crystallographic evidence for folded conformation due to arene interactions
  作者：Kamlakar Avasthi、Sheikh M. Farooq、Chandralata Bal、Rishi Kumar、Ashish K. Tewari、Prakas R. Maulik

  DOI：10.1016/j.molstruc.2006.12.029

  日期：2007.10

  4-d]pyrimidin-1-yl)propyl]-5,7-dimethyl/ethyl-sulfanyl-1H/2H/3H-triazolo[4,5-d]pyrimidines (6 and 8) show intramolecularly stacked conformation in solution. X-ray crystallography of one dissymmetrical ‘Leonard/trimethylene’ linker compound (6b) based on two different heterocycles namely pyrazolo[3,4-d]pyrimidine core and triazolo[4,5-d]pyrimidine, for the first time, shows unusual U-motif formed due to intramolecular

  摘要 几种新合成的不对称“Leonard/三亚甲基接头”化合物 1/2/3-[(4,6-二甲基硫烷基-1H-吡唑并[3,4-d]嘧啶-1-基)丙基]-5的质子核磁共振分析,7-二甲基/乙基-硫基-1H/2H/3H-三唑并[4,5-d]嘧啶（6和8）在溶液中显示分子内堆积构象。基于两种不同的杂环，即吡唑并[3,4-d]嘧啶核和三唑并[4,5-d]嘧啶，一种不对称的“伦纳德/三亚甲基”接头化合物 (6b) 的 X 射线晶体学首次显示由于分子内 π-π 相互作用形成了不寻常的 U 基序，这类似于早期相关的基于十个对称（1 和 2）和一个不对称化合物（3）的吡唑并[3,4-d]嘧啶核。由于弱的分子间 CH…N 和 CH…S 相互作用，新化合物 (6b) 的超分子结构显示出不寻常的链基序。更重要的是，新化合物 (6b) 显示出任何早期化合物 (1、2 和 3) 未显示的 S…芳烃相互作用。
• Avasthi, K.; Chandra, T.; Bhakuni, D. S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1995, vol. 34, # 11, p. 944 - 949
  作者：Avasthi, K.、Chandra, T.、Bhakuni, D. S.

  DOI：——

  日期：——
• 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
  作者：Kamlakar Avasthi、Sheikh M. Farooq、Resmi Raghunandan、Prakas R. Maulik

  DOI：10.1016/j.molstruc.2005.10.005

  日期：2006.3

  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.