2,6-dichloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine | 90348-54-2

• 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: 2,6-dichloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine
• 英文别名: 2,6-dichloro-9-(tetrahydrofuran-2-yl)-9H-purine；2,6-dichloro-9-(2-tetrahydrofuranyl)-9H-purine；2,6-dichloro-9-(tetrahydrofuran-2-yl)purine；2,6-dichloro-9-tetrahydrofuran-2-yl-9H-purine；9--2,6-dichlor-purin；2,6-dichloro-9-(oxolan-2-yl)purine
• CAS: 90348-54-2
• 化学式: C₉H₈Cl₂N₄O
• 分子量: 259.095
• InChiKey: MRCRQUGOOQUHKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  52.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,6-dichloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine 在 氨 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以63%的产率得到6-amino-2-chloro-9-(2-tetrahydrofuranyl)-9H-purine
  参考文献：
  名称：

  [EN] SUBSTITUTED ADENINES AND THE USE THEREOF
  [FR] ADENINES SUBSTITUEES ET LEUR UTILISATION

  摘要：

  这项发明涉及式(I)的化合物及其在治疗细菌感染中的应用。

  公开号：

  WO2006040558A1
• 作为产物：
  描述：

  四氢呋喃 、 2,6-二氯嘌呤 在 全氟碘代丁烷 、 caesium carbonate 作用下， 反应 12.0h， 以70%的产率得到2,6-dichloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine
  参考文献：
  名称：

  卤素键促进的α-C-H醚化胺用于合成半羟色胺

  摘要：

  已经完成了醚/硫醚与各种NH化合物的卤素键促进的简单α-CH胺化反应。在存在低成本且易于获得的全氟丁基碘的情况下，在热或可见光辐照条件下，迅速组装了各种各样的半胱氨酸醚衍生物，包括有价值的半胱氨酸醚。机理研究表明，形成了卤素键加合物，自由基链途径可能起作用。通过制备抗病毒和抗肿瘤药物替加福证明了该方法的综合应用。

  DOI：

  10.1002/adsc.201800006

文献信息

• Intermolecular Hydrogen Abstraction Reaction between Nitrogen Radicals in Purine Rings and Alkyl Ethers: A Highly Selective Method for the Synthesis of N-9 Alkylated Purine Nucleoside Derivatives
  作者：Hai-Ming Guo、Chao Xia、Hong-Ying Niu、Xiao-Ting Zhang、Si-Nan Kong、Dong-Chao Wang、Gui-Rong Qu

  DOI：10.1002/adsc.201000682

  日期：2011.1.10

  A highly selective method for the synthesis of N‐9 alkylated purine nucleoside derivatives via an intermolecular hydrogen abstraction reaction between nitrogen radicals in purine rings and alkyl ethers was developed. Novel purine nucleoside derivatives were obtained with good to high yields in the presence of (diacetoxyiodo)benzene (DIB) and iodine in one‐step reaction.

  开发了一种通过嘌呤环中的氮自由基与烷基醚之间的分子间氢抽象反应来合成N-9烷基化嘌呤核苷衍生物的高选择性方法。在（二乙酰氧基碘）苯（DIB）和碘的存在下，一步反应可以得到高纯度到高产率的新型嘌呤核苷衍生物。
• N -9 Alkylation of purines via light-promoted and metal-free radical relay
  作者：Runze Mao、Lifeng Sun、Yong-Shi Wang、Min-Min Zhou、De-Cai Xiong、Qin Li、Xin-Shan Ye

  DOI：10.1016/j.cclet.2017.08.005

  日期：2018.1

  approach to the synthesis of N -9 alkylated purine nucleoside derivatives, via a CF 3 radical triggered radical relay pathway, has been developed. Purine nucleoside derivatives were prepared regioselectively in good to high yields. Photosensitizers and metals are free in this transformation. Visible light or even sunlight can be used as the source of light for the reactions.

  摘要开发了一种无金属且光促进的方法，该方法通过CF 3自由基触发的自由基中继途径合成N -9烷基化嘌呤核苷衍生物。嘌呤核苷衍生物以良好至高产率区域选择性地制备。在这种转化过程中，光敏剂和金属是免费的。可见光或什至阳光都可以用作反应的光源。
• Copper-catalyzed N-alkoxyalkylation of nucleobases involving direct functionalization of sp3 C–H bonds adjacent to oxygen atoms
  作者：Rui Huang、Chunsong Xie、Lin Huang、Jinhua Liu

  DOI：10.1016/j.tet.2012.11.020

  日期：2013.1

  N-Alkoxyalkylation of nucleobases was realized by the copper-catalyzed peroxide-promoted coupling of nucleobases with readily available saturated ethers. Both purines and pyrimidines could be N-alkoxyalkylated through this method in moderate to good yields. 2D-NMR revealed that N9-alkoxyalkylation preferentially occurred when purines were used in this reaction.

  核碱基的N-烷氧基烷基化是通过铜催化的过氧化物促进的核碱基与易于获得的饱和醚的偶联而实现的。通过该方法，嘌呤和嘧啶均可被N-烷氧基烷基化，产率中等至良好。2D-NMR显示当在该反应中使用嘌呤时，优先发生N 9-烷氧基烷基化。
• C–H Amination of Purine Derivatives via Radical Oxidative Coupling
  作者：Zheng Luo、Ziyang Jiang、Wei Jiang、Dongen Lin

  DOI：10.1021/acs.joc.8b00066

  日期：2018.4.6

  An oxidative coupling reaction between purines and alkyl ethers/benzyl compounds was developed to synthesize a series of N9 alkylated purine derivatives using n-Bu4NI as a catalyst and t-BuOOH as an oxidant. This protocol uses commercially available, inexpensive catalysts and oxidants and has a wide range of substrates with a simple operation.

  开发了嘌呤与烷基醚/苄基化合物之间的氧化偶联反应，以n -Bu 4 NI为催化剂，t -BuOOH为氧化剂，合成了一系列N9烷基化的嘌呤衍生物。该方案使用可商购的，廉价的催化剂和氧化剂，并具有操作简单的多种底物。
• [EN] 9-(2-OXACYCLOALKYL)-9H-PURINE-2,6-DIAMINE DERIVATIVES AND THEIR USE FOR THE TREATMENT OF SKIN DISORDERS<br/>[FR] DÉRIVÉS DE 9-(2-OXACYCLOALKYL)-9H-PURINE-2,6-DIAMINE ET LEUR UTILISATION POUR LE TRAITEMENT DE TROUBLES CUTANÉS
  申请人：UNIV PALACKEHO

  公开号：WO2018196893A1

  公开（公告）日：2018-11-01

  The invention relates to N 2 ,N 6 -disubstituted-9-(2-oxacycloalkyl)-9H-purine-2,6-diamine derivatives and their use as drugs and cosmetics. The compounds of the present invention exhibit a number of biological activities associated with oxidative stress inhibition, especially anti-aging, anti-inflammatory and anti-neurodegenerative biological activities. The invention also relates to cosmetic and pharmaceutical compositions containing such derivatives as active agents.

  该发明涉及N2，N6-二取代-9-(2-氧杂环烷基)-9H-嘌呤-2,6-二胺衍生物及其作为药物和化妆品的用途。本发明的化合物展现出与氧化应激抑制相关的多种生物活性，特别是抗衰老、抗炎和抗神经退行性生物活性。该发明还涉及含有这些衍生物作为活性剂的化妆品和药用组合物。