3-bromo-4-propoxy-1H-pyrazolo<3,4-d>pyrimidin-6-amine | 220906-53-6

• 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: 3-bromo-4-propoxy-1H-pyrazolo<3,4-d>pyrimidin-6-amine
• 英文别名: 3-bromo-4-propoxy-2H-pyrazolo[3,4-d]pyrimidin-6-amine
• CAS: 220906-53-6
• 化学式: C₈H₁₀BrN₅O
• 分子量: 272.104
• InChiKey: SXOKMZUGOSDJJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  89.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-bromo-4-propoxy-1H-pyrazolo<3,4-d>pyrimidin-6-amine 在 氢氧化钾 、 sodium hydroxide 、 三(3,6-二氧杂庚基)胺 作用下， 以 丙醇 、 乙腈 为溶剂， 反应 1.83h， 生成 6-amino-3-bromo-1-(2-deoxy-β-D-erythro-pentofuranosyl)-1,5-dihydro-4H-pyrazole<3,4-d>pyrimidin-4-one
  参考文献：
  名称：

  TheHigh-Anti Conformation of 7-Halogenated 8-Aza-7-deaza-2′-deoxy-guanosines: A Study of the Influence of Modified Bases on the Sugar Structure of Nucleosides

  摘要：

  The conformation of the 7-bromo- and 7-iodo-substituted 8-aza-7-deazapurine nucleosides 1 and 2 in the solid state and in aqueous solution was studied by single-crystal X-ray analyses and by H-1-NMR spectroscopy. In the solid state, both compounds display a high-anti conformation around the glycosylic bond, and their 2'-deoxy-beta-D-ribofuranose moieties adopt an N-type sugar puckering. The orientation of the exocyclic C(4')-C(5') bond was found to be crp in both cases. In D2O solution, both compounds display i) an 8-10% higher N-conformer population than 2'-deoxyguanosine and ii) a preference of the -sc conformation about the C(4')-C(5') bond. A comparative study on the influence of modified bases on the sugar structure of nucleosides is made.

  DOI：

  10.1002/(sici)1522-2675(19990113)82:1<105::aid-hlca105>3.0.co;2-3
• 作为产物：
  描述：

  4-propoxy-1H-pyrazolo<3,4-d>pyrimidin-6-amine 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 以64%的产率得到3-bromo-4-propoxy-1H-pyrazolo<3,4-d>pyrimidin-6-amine
  参考文献：
  名称：

  TheHigh-Anti Conformation of 7-Halogenated 8-Aza-7-deaza-2′-deoxy-guanosines: A Study of the Influence of Modified Bases on the Sugar Structure of Nucleosides

  摘要：

  The conformation of the 7-bromo- and 7-iodo-substituted 8-aza-7-deazapurine nucleosides 1 and 2 in the solid state and in aqueous solution was studied by single-crystal X-ray analyses and by H-1-NMR spectroscopy. In the solid state, both compounds display a high-anti conformation around the glycosylic bond, and their 2'-deoxy-beta-D-ribofuranose moieties adopt an N-type sugar puckering. The orientation of the exocyclic C(4')-C(5') bond was found to be crp in both cases. In D2O solution, both compounds display i) an 8-10% higher N-conformer population than 2'-deoxyguanosine and ii) a preference of the -sc conformation about the C(4')-C(5') bond. A comparative study on the influence of modified bases on the sugar structure of nucleosides is made.

  DOI：

  10.1002/(sici)1522-2675(19990113)82:1<105::aid-hlca105>3.0.co;2-3

文献信息

• TheHigh-Anti Conformation of 7-Halogenated 8-Aza-7-deaza-2′-deoxy-guanosines: A Study of the Influence of Modified Bases on the Sugar Structure of Nucleosides
  作者：Frank Seela、Georg Becher、Helmut Rosemeyer、Hans Reuter、Guido Kastner、Igor A. Mikhailopulo

  DOI：10.1002/(sici)1522-2675(19990113)82:1<105::aid-hlca105>3.0.co;2-3

  日期：1999.1.13

  The conformation of the 7-bromo- and 7-iodo-substituted 8-aza-7-deazapurine nucleosides 1 and 2 in the solid state and in aqueous solution was studied by single-crystal X-ray analyses and by H-1-NMR spectroscopy. In the solid state, both compounds display a high-anti conformation around the glycosylic bond, and their 2'-deoxy-beta-D-ribofuranose moieties adopt an N-type sugar puckering. The orientation of the exocyclic C(4')-C(5') bond was found to be crp in both cases. In D2O solution, both compounds display i) an 8-10% higher N-conformer population than 2'-deoxyguanosine and ii) a preference of the -sc conformation about the C(4')-C(5') bond. A comparative study on the influence of modified bases on the sugar structure of nucleosides is made.