9-phenyladenine | 20145-09-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 9-phenyladenine
• 英文别名: SQ 22517；9-Phenylpurin-6-amine
• CAS: 20145-09-9
• 化学式: C₁₁H₉N₅
• 分子量: 211.226
• InChiKey: QOZYZBRNUYGQNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  9-phenyladenine 在 硫酸 、 sodium nitrite 作用下， 生成 9-苯基-3H-嘌呤-6-酮
  参考文献：
  名称：

  Purines. VI. The Preparation of Certain 6-Substituted-and 6,9-Disubstituted Purines¹

  摘要：

  DOI：

  10.1021/jo01108a007
• 作为产物：
  描述：

  6-氯-9-苯基嘌呤 在 ammonium hydroxide 作用下， 反应 16.0h， 以95%的产率得到9-phenyladenine
  参考文献：
  名称：

  Synthetic Strategies to 9-Substituted 8-Oxoadenines

  摘要：

  Three synthetic routes to 9-substituted 8-oxoadenines have been studied: bromination of adenine followed by N-9-alkylation/arylation and finally hydrolysis; bromination of adenine, hydrolysis, and N-functionalization as the last step; and N-9-alkylation of adenine, halogenation, and finally hydrolysis. As long as the N-9-functional group is compatible with conditions required for introduction of the halogen, the latter strategy was the most efficient. Also, a strategy starting from 5-amino-4,6-dichloropyrimidine was found to be a very good alternative for synthesis of 9-substituted 8-oxoadenines. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) to view the free supplemental file.

  DOI：

  10.1080/00397911.2011.642051

文献信息

• Direct <i>N</i>⁹-arylation of purines with aryl halides
  作者：Anders Foller Larsen、Trond Ulven

  DOI：10.1039/c3cc48642g

  日期：——

  The reported protocol is the first to be demonstrated to efficiently couple aryl halides to purines with predictable selectivity.

  据报道的协议是第一个被证明能有效地将芳基卤化物与嘌呤以可预测的选择性偶联的协议。
• <i>N</i>-Arylation of (hetero)arylamines using aryl sulfamates and carbamates <i>via</i> C–O bond activation enabled by a reusable and durable nickel(0) catalyst
  作者：Iman Dindarloo Inaloo、Sahar Majnooni、Hassan Eslahi、Mohsen Esmaeilpour

  DOI：10.1039/d0nj01610a

  日期：——

  elemental analysis techniques. The reaction proceeded via carbon–oxygen bond cleavage of (hetero)aryl carbamates and sulfamates under simple and mild conditions without the use of any external ligands. This method demonstrated functional group tolerance in the N-arylation of various nitrogen-containing compounds as well as aliphatic amines, anilines, pyrroles, pyrazoles, imidazoles, indoles, and indazoles

  已经开发出了一种有效且通用的芳基胺化方案，使用了可磁回收的Ni（0）基纳米催化剂。该新型稳定催化剂是在EDTA改性的Fe 3 O 4 @SiO 2上制备的，并通过FT-IR，EDX，TEM，XRD，DLS，FE-SEM，XPS，NMR，TGA，VSM，ICP和元素分析技术进行了研究。该反应通过在简单温和的条件下不使用任何外部配体的情况下，通过（杂）芳基氨基甲酸酯和氨基磺酸酯的碳-氧键裂解来进行。该方法证明了N中的官能团耐受性各种含氮化合物以及脂肪族胺，苯胺，吡咯，吡唑，咪唑，吲哚和吲唑的芳基化，收率良好。此外，该催化剂可以通过使用外部磁场容易地回收，并且可以直接重复使用至少六次而不会显着降低其活性。
• 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。
• Selective copper catalysed aromatic N-arylation in water
  作者：Jens Engel-Andreasen、Bharat Shimpukade、Trond Ulven

  DOI：10.1039/c2gc36589h

  日期：——

  4,7-Dipyrrolidinyl-1,10-phenanthroline (DPPhen) was identified as an efficient ligand for copper catalysed selective aromatic N-arylation in water. N-Arylation of indoles, imidazoles and purines proceeds with moderate to excellent yields and complete selectivity over aliphatic amines. Aqueous medium and the possibility for low metal and ligand loadings give the process a benign environmental profile.

  4,7-二吡咯烷基-1,10-菲蒽 (DPPhen) 被确定为一种高效的配体，用于在水中催化选择性芳香族氮芳基化的铜催化反应。吲哚、咪唑及嘌呤的氮芳基化反应以中等到优良的产率进行，并对脂肪胺具有完全的选择性。水相介质和低金属及配体用量的可能性使该过程具有良好的环境特征。
• 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)