N⁹-(4-methoxyphenyl)adenine | 127820-21-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N⁹-(4-methoxyphenyl)adenine
• 英文别名: 9-(4-methoxyphenyl)-9H-purin-6-amine；6-amino-9-(4-methoxyphenyl)purine；9-(4-methoxyphenyl)-adenine；9-(4-methoxyphenyl)adenine；9-(4-methoxyphenyl)purin-6-amine
• CAS: 127820-21-7
• 化学式: C₁₂H₁₁N₅O
• 分子量: 241.252
• InChiKey: YMODPHYHXIOBEG-UHFFFAOYSA-N

物化性质

• 熔点：
  >290 °C (decomp)(Solv: ethyl ether (60-29-7))
• 沸点：
  493.9±55.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  78.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-溴黎芦醚 、 N⁹-(4-methoxyphenyl)adenine 在 copper(l) iodide 、 palladium diacetate 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 60.0h， 以26%的产率得到8-(3,4-dimethoxyphenyl)-9-(4-methoxyphenyl)-adenine
  参考文献：
  名称：

  通过Suzuki交叉偶联，N-芳基化和直接CH芳基化反应的组合合成6,8,9-三-和2,6,8,9-四取代的嘌呤。

  摘要：

  通过区域选择性的Suzuki交叉偶联反应和/或Cu催化的N-芳基化与直接CH芳基化的组合，开发了几种类型的二芳基，三芳基和四芳基嘌呤衍生物的合成的新型实用方法。通过将6-氯-或2,6-二氯-9-异丙基嘌呤与芳基硼酸进行一次或两次交叉偶联，然后进行Pd催化，可制备6,8-二芳基-和2,6,8-三芳基-9-异丙基嘌呤由芳基卤化物进行CH芳基化至位置8。6-氯嘌呤和腺嘌呤与硼酸进行Cu催化的N-芳基化至位置9，然后与AlMe3交叉偶联和/或CH芳基化获得8,9-二芳基-6-甲基嘌呤或8,9-二芳基腺嘌呤（在位置6处带有腺嘌呤的部分N-芳基化产物）。该方法适用于构建修饰嘌呤的小型文库。

  DOI：

  10.1021/jo8018126
• 作为产物：
  描述：

  N6-二boc 腺嘌呤 在 copper diacetate air 、 三乙胺 、 乙酰氯 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 146.0h， 生成 N⁹-(4-methoxyphenyl)adenine
  参考文献：
  名称：

  Efficient N-Arylation and N-Alkenylation of the Five DNA/RNA Nucleobases

  摘要：

  [GRAPHICS]A general approach to N-arylation and N-alkenylation of all five DNA/RNA nucleobases at the nitrogen atom normally attached to the sugar moiety in DNA or RNA has been developed. Various protected or masked nucleobases engaged readily in the copper-mediated Chan-Lam-Evans-modified Ullmann condensation with a range of different boronic acids at room temperature and were subsequently converted to the corresponding deprotected or unmasked adducts. Different N-3-protecting groups were examined in the case of thymine, where the benzoyl group afforded the highest yields. A 4-alkylthio-substituted pyrimidin-2(1H)-one served as both a cytosine and a uracil precursor and was N-arylated and N-alkenylated in high yields. Adenine was efficiently and selectively N-arylated and N-alkenylated at the N-9 position by employing a bis-Boc-protected adenine derivative, while a bis-Boc-protected 2-amino-6-chloropurine served as guanine precursor and could also be selectively N-9-arylated and N-9-alkenylated.

  DOI：

  10.1021/jo061694i

文献信息

• Purine derivatives as competitive inhibitors of human erythrocyte membrane phosphatidylinositol 4-kinase
  作者：Rodney C. Young、Martin Jones、Kevin J. Milliner、Kishore K. Rana、John G. Ward

  DOI：10.1021/jm00170a005

  日期：1990.8

  The possibility of deriving a potent, cell-penetrating inhibitor of human erythrocyte PI 4-kinase, competitive with respect to ATP, has been investigated in a series of purine derivatives and analogues. The purine nucleus is not essential for binding to the ATP site but offers the advantage of synthetic accessibility to its derivatives. The optimum substitution pattern in purine was found to be an

  在一系列嘌呤衍生物和类似物中，已经研究了获得有效的，可穿透细胞的人红细胞PI 4-激酶抑制剂（相对于ATP具有竞争性）的可能性。嘌呤核对于结合到ATP位点不是必不可少的，但具有合成易接近其衍生物的优势。发现嘌呤中的最佳取代方式是6-位的电子释放取代基（例如氨基，如腺嘌呤1），在8位或最好在9位是紧密的亲脂基团，表明N-1孤对的重要性以及8和9取代基对结合的疏水作用。合成的最有效的抑制剂是9-环己基腺嘌呤（54），其表观Ki值为3.7 microM。
• A Mild and Efficient Method for<i>N</i>‐Arylnucleobase Synthesis<i>via</i>the Cross‐Coupling Reactions of Nucleobases with Arylboronic Acids Catalyzed by Simple Copper Salts
  作者：Lan Tao、Yang Yue、Ji Zhang、Shan‐Yong Chen、Xiao‐Qi Yu

  DOI：10.1002/hlca.200890107

  日期：2008.6

  A simple and efficient copper-salt catalyzed N-arylation of nucleobases is reported. In a mixed solvent of MeOH and H2O, the coupling products were obtained in moderate to excellent yields at room temperature within a short time. A variety of substituted N-aryl nucleobases can be prepared through this procedure.

  报道了一种简单而有效的铜盐催化的核碱基的N-芳基化。在MeOH和H 2 O的混合溶剂中，在短时间内在室温下以中等至优异的产率获得偶联产物。通过该程序可以制备各种取代的N-芳基核碱基。
• Copper Nanoparticle-Doped Silica Cuprous Sulfate as a Highly Efficient and Reusable Heterogeneous Catalysis for N-Arylation of Nucleobases and N-Heterocyclic Compounds
  作者：Mohammad Soltani Rad、Somayeh Behrouz、Mohammad Doroodmand、Noushin Moghtaderi

  DOI：10.1055/s-0030-1260236

  日期：2011.12

  A facile and simple protocol for Ullmann-type N-arylation of nucleobases with aryl halides is described using copper nanoparticle-doped silica cuprous sulfate (CN-DSCS) as a new and efficient heterogeneous catalysis. In this method, treatment of various nucleobases and aryl halides in the presence of DBU and CN-DSCS in refluxing DMF furnishes the corresponding N-aryl adducts in reasonable to good yields. The CN-DSCS was fully characterized by different microscopic, spectroscopic and physical techniques, including scanning electron microscopy (SEM), transmission electron microscopy (TEM), atomic force microscopy (AFM), X-ray diffraction (XRD), inductively coupled plasma (ICP) analysis, thermogravimetric analysis (TGA), and FT-IR. The CN-DSCS was proved to be a chemically and thermally stable, cheap, and environmentally compatible heterogeneous nanocatalyst that can be reused for many consecutive experiments without any considerable decrease in its reactivity.

  我们描述了一种简单且有效的乌尔曼型N-芳基化核苷酸与芳基卤化物的合成方法，使用掺铜纳米颗粒的二氧化硅硫酸铜（CN-DSCS）作为新的高效的非均相催化剂。在该方法中，在DBU和CN-DSCS存在下，将多种核苷酸与芳基卤化物在回流的DMF中处理，能够合理至良好地生成相应的N-芳基加成物。通过扫描电子显微镜（SEM）、透射电子显微镜（TEM）、原子力显微镜（AFM）、X射线衍射（XRD）、电感耦合等离子体（ICP）分析、热重分析（TGA）和FT-IR等多种显微、光谱和物理技术对CN-DSCS进行了全面表征。研究表明，CN-DSCS是一种化学和热稳定性强、廉价且环境友好的非均相纳米催化剂，可以在多个连续实验中重复使用，而其反应活性几乎没有显著下降。
• Copper-Catalyzed Cross-Coupling Reactions of Nucleobases with Arylboronic Acids: An Efficient Access toN-Arylnucleobases
  作者：Yang Yue、Zhang-Guo Zheng、Bo Wu、Chuan-Qin Xia、Xiao-Qi Yu

  DOI：10.1002/ejoc.200500589

  日期：2005.12

  An efficient avenue for the direct N-arylation of nucleobases with arylboronic acids that is catalyzed by simple copper salts was discovered. The N-arylnucleobases were obtained in excellent yields at room temperature within 45 min when methanol and water were used as a mixed solvent. Under these conditions, the coupling reaction tolerates both electron-donating and electron-withdrawing substituents

  发现了通过简单的铜盐催化核碱基与芳基硼酸直接 N-芳基化的有效途径。当使用甲醇和水作为混合溶剂时，在室温下 45 分钟内以优异的产率获得 N-芳基核碱基。在这些条件下，偶联反应可以耐受苯基硼酸的邻位、间位或对位上的给电子和吸电子取代基，并以中等至极好的产率得到相应的偶联产物。实验结果表明，该路线是合成N-芳基碱基的最有效、最简便、最温和的方法。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• [EN] PHOTOREDOX-CATALYZED DIRECT C-H FUNCTIONALIZATION OF ARENES<br/>[FR] FONCTIONNALISATION DIRECTE DE LA LIAISON C-H D'ARÈNES CATALYSÉE PAR UNE RÉACTION PHOTORÉDOX
  申请人：UNIV NORTH CAROLINA CHAPEL HILL

  公开号：WO2016196816A1

  公开（公告）日：2016-12-08

  The invention generally relates to methods of making substituted arenes via direct C-H amination. More specifically, methods of making para- and ortho-substituted arenes via direct C-H amination are disclosed. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

  该发明通常涉及通过直接C-H氨化制备取代芳烃的方法。更具体地，公开了通过直接C-H氨化制备对位和邻位取代芳烃的方法。本摘要旨在作为在特定领域搜索的扫描工具，并不旨在限制本发明。