6-([1,1′-biphenyl]-2-yl)-9-benzyl-9H-purine | 1284287-13-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 6-([1,1′-biphenyl]-2-yl)-9-benzyl-9H-purine
• 英文别名: 9-benzyl-6-([1,1'-biphenyl]-2-yl)-9H-purine；6-([1,1'-biphenyl]-2-yl)-9-benzyl-9H-purine；9-Benzyl-6-(2-phenylphenyl)purine；9-benzyl-6-(2-phenylphenyl)purine
• CAS: 1284287-13-3
• 化学式: C₂₄H₁₈N₄
• 分子量: 362.434
• InChiKey: QHQXBJUPWGGZBE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 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-benzyl-6-phenyl-9H-purine 在 tris(bipyridine)ruthenium(II) dichloride hexahydrate 作用下， 以 甲醇 为溶剂， 反应 8.0h， 生成 6-([1,1′-biphenyl]-2-yl)-9-benzyl-9H-purine
  参考文献：
  名称：

  Visible-Light-Mediated Monoselective Ortho C–H Arylation of 6-Arylpurine Nucleosides with Diazonium Salts

  摘要：

  A combined palladium- and photoredox-catalyzed monoselective arylation of 6-arylpurine nucleosides has been developed by employing purine as a directing group via the photoredox reaction, and many functional groups are well tolerated in this direct C-H arylation condition. Various of functionalized purines (nucleosides) which are potentially of great importance in medicinal chemistry could be obtained under visible light irradiation at room temperature within 4 h.

  DOI：

  10.1021/acs.joc.7b00659

文献信息

• 可见光催化反应合成6-联芳基取代嘌呤(核苷)的方法
  申请人：河南师范大学

  公开号：CN107163048A

  公开（公告）日：2017-09-15

  本发明涉及一种采用可见光合成6‑联芳基取代嘌呤(核苷)的方法，属于有机化学领域。以6‑芳基嘌呤(核苷)和芳基重氮四氟硼酸盐为原料，以2‑8％的醋酸钯为催化剂，0.5‑3.0％的六水合三联吡啶氯化钌为光催化剂，反应后得到6‑联芳基嘌呤(核苷)，收率中等至良好。该合成方法原料易得，反应条件温和条件，提供了一种简便、绿色、高效的6‑联芳基取代嘌呤(核苷)的合成途径，同时为其它6‑位联芳基取代嘌呤(核苷)的合成提供了有效的方法。
• Direct Arylation of 6-Phenylpurine and 6-Arylpurine Nucleosides by Ruthenium-Catalyzed CH Bond Activation
  作者：Mahesh K. Lakshman、Ashoke C. Deb、Raghu Ram Chamala、Padmanava Pradhan、Ramendra Pratap

  DOI：10.1002/anie.201104035

  日期：2011.11.25

  One aryl or two? The title reaction predominantly gives the monoarylation products with various amounts of diarylation product being observed in almost all cases (see scheme). Aryl iodides as well as aryl bromides were reactive under the optimized reaction conditions. The multiple nitrogen atoms in the purine, and oxygen atoms in the saccharide posed no problems in these transformations.

  一个芳基还是两个？标题反应主要产生单芳基化产物，在几乎所有情况下都观察到不同量的二芳基化产物（参见方案）。芳基碘化物和芳基溴化物在优化的反应条件下具有反应性。嘌呤中的多个氮原子和糖中的氧原子在这些转化中没有问题。
• Pd(II)-Catalyzed <i>Ortho</i> Arylation of 6-Arylpurines with Aryl Iodides via Purine-Directed C−H Activation: A New Strategy for Modification of 6-Arylpurine Derivatives
  作者：Hai-Ming Guo、Li-Li Jiang、Hong-Ying Niu、Wei-Hao Rao、Lei Liang、Run-Ze Mao、De-Yang Li、Gui-Rong Qu

  DOI：10.1021/ol200405w

  日期：2011.4.15

  Purine is utilized as a new directing group for the Pd-catalyzed monoarylation of 6-arylpurines with simple aryl iodides via C H bond activation in good yields, providing a complementary tool for the modification of 6-arylpurines (nucleosides). Most importantly, purine can be used as a building block for nucleoside derivatives, and the use of purine as a directing group helps avoid additional synthetic steps.
• Visible-Light-Mediated Monoselective Ortho C–H Arylation of 6-Arylpurine Nucleosides with Diazonium Salts
  作者：Lei Liang、Ming-Sheng Xie、Hai-Xia Wang、Hong-Ying Niu、Gui-Rong Qu、Hai-Ming Guo

  DOI：10.1021/acs.joc.7b00659

  日期：2017.6.2

  A combined palladium- and photoredox-catalyzed monoselective arylation of 6-arylpurine nucleosides has been developed by employing purine as a directing group via the photoredox reaction, and many functional groups are well tolerated in this direct C-H arylation condition. Various of functionalized purines (nucleosides) which are potentially of great importance in medicinal chemistry could be obtained under visible light irradiation at room temperature within 4 h.