9-allyl-2-chloro-9H-purine | 1526929-26-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 9-allyl-2-chloro-9H-purine
• 英文别名: 2-Chloro-9-prop-2-enylpurine；2-chloro-9-prop-2-enylpurine
• CAS: 1526929-26-9
• 化学式: C₈H₇ClN₄
• 分子量: 194.623
• InChiKey: KFWCNRWHZJCRPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  9-allyl-2,6-dichloro-9H-purine 在 水 、 氧气 、 一水合肼 、 copper(II) sulfate 作用下， 以 乙醇 为溶剂， 反应 8.0h， 生成 9-allyl-2-chloro-9H-purine
  参考文献：
  名称：

  Efficient synthesis of nebularine and vidarabine via dehydrazination of (hetero)aromatics catalyzed by CuSO₄in water

  摘要：

  首次在催化量的CuSO4存在下实现了一步简单的脱氢反应。以CuSO4 (2 mol%)为催化剂，水为溶剂，脱氢产物获得了良好的产率（66-95%）。此外，成功合成了药物 nebularine 和 Vidarabine，并且 Vidarabine 可在0.923公斤规模生产，显示出良好的工业应用潜力。

  DOI：

  10.1039/c3gc41658e

文献信息

• The synthesis of nebularine and its analogs <i>via</i> oxidative desulfuration in aqueous nitric acid
  作者：Ran Xia、Li-Ping Sun、Gui-Rong Qu

  DOI：10.1080/10426507.2016.1225057

  日期：2017.1.2

  GRAPHICAL ABSTRACT ABSTRACT The synthesis of nebularine and its analogs has been achieved via oxidative desulfuration in H2O for the first time. With 50% HNO3 as an oxidant and solvent, 18 products were obtained in good yields (70%–94%). The oxidative desulfuration system could tolerate different functional groups including fluoro, chloro, amino, alkyl, allyl, ribosyl, deoxyribosyl, and arabinofuranosyl

  图形摘要 摘要 nebularine 及其类似物的合成首次通过在 H2O 中氧化脱硫实现。以 50% HNO3 作为氧化剂和溶剂，以良好的收率 (70%–94%) 获得了 18 种产物。氧化脱硫系统可以耐受不同的官能团，包括氟、氯、氨基、烷基、烯丙基、核糖基、脱氧核糖基和阿拉伯呋喃糖基。更重要的是，药物 nebularine 可以在 20 g 的规模上成功获得，这使得该路线对工业应用更具吸引力。
• Purine derivatives, process for their preparation and use thereof
  申请人：——

  公开号：US20030187261A1

  公开（公告）日：2003-10-02

  The present invention relates to new purine derivatives and their deaza- and aza-analogues, methods for preparing said derivatives, and to their use in suitable utilities, in particular their use in diagnostics and therapeutic methods. The invention relates in particular to purine derivatives with an inhibitory effect on for example cyclin-dependent kinase proteins (sdks), viruses, and proliferation of haemotapoietic and cancer cells.

  本发明涉及新的嘌呤衍生物及其去氮和氮杂类似物，制备这些衍生物的方法，以及它们在适当的实用程序中的使用，特别是它们在诊断和治疗方法中的使用。本发明特别涉及具有抑制作用的嘌呤衍生物，例如对于细胞周期依赖性激酶蛋白（sdks）、病毒和造血和癌细胞增殖等。
• PURINE DERIVATIVES, PROCESS FOR THEIR PREPARATION AND USE THEREOF
  申请人：UNIVERSITAIRE INSTELLING ANTWERPEN

  公开号：EP1244668A1

  公开（公告）日：2002-10-02
• [EN] PURINE DERIVATIVES, PROCESS FOR THEIR PREPARATION AND USE THEREOF<br/>[FR] DERIVES DE PURINE, PROCEDE DE PREPARATION ET UTILISATION DE CES DERNIERS
  申请人：UNIVERSITAIRE INSTELLING ANTWE

  公开号：WO2001049688A1

  公开（公告）日：2001-07-12

  2-, 6-, 8-, 9-monosubstituted, 2,6-, 2,9-, 6,8-, 6,9-disubstituted and 2,6,8-, 2,6,9-, 6,8,9-trisubstituted purine derivatives and their deaza- and aza- analogues with an inhibitor effect with respect to cyclin-dependent kinase proteins (cdks). Their use as anticancer, anti-inflammatory, antiviral, antineurodegenerative, neurodepressive and immunosuppressive compounds.
• Efficient synthesis of nebularine and vidarabine via dehydrazination of (hetero)aromatics catalyzed by CuSO₄in water
  作者：Ran Xia、Ming-Sheng Xie、Hong-Ying Niu、Gui-Rong Qu、Hai-Ming Guo

  DOI：10.1039/c3gc41658e

  日期：——

  A simple dehydrazination reaction has been achieved in the presence of a catalytic amount of CuSO4 for the first time. With CuSO4 (2 mol%) as a catalyst and water as a solvent, the dehydrazination products were obtained in good yields (66–95%). Moreover, the drugs nebularine and vidarabine were afforded successfully, and vidarabine could be produced on a 0.923 kg scale, which shows good potential for industrial applications.

  首次在催化量的CuSO4存在下实现了一步简单的脱氢反应。以CuSO4 (2 mol%)为催化剂，水为溶剂，脱氢产物获得了良好的产率（66-95%）。此外，成功合成了药物 nebularine 和 Vidarabine，并且 Vidarabine 可在0.923公斤规模生产，显示出良好的工业应用潜力。