9-ethyl-6-phenyl-9H-purine | 83026-89-5

• 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: 9-ethyl-6-phenyl-9H-purine
• 英文别名: 9-Ethyl-6-phenylpurine；9-ethyl-6-phenylpurine
• CAS: 83026-89-5
• 化学式: C₁₃H₁₂N₄
• 分子量: 224.265
• InChiKey: OPTUVTHIBYJEPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-ethyl-6-phenyl-9H-purine 以 二氯甲烷 、 乙二醇甲醚 为溶剂， 反应 84.0h， 生成 [Ir(9-ethyl-6-phenylpurine)₂(4,4′-di-tert-butyl-2,2′-dipyridine)]PF₆
  参考文献：
  名称：

  来自嘌呤核碱基的磷光 Ir(III) 复合物

  摘要：

  我们报告了衍生自 6-苯基嘌呤核苷和核苷酸的新型中性和阳离子磷光杂配 Ir( III ) 配合物的制备和研究。通式 Ir(C^N) 2 (acac) 7和8a-c (HC^N = 9-取代-6-苯基嘌呤)的中性配合物在光激发下呈橙红色发光，寿命短，量子产率高(0.42–0.65) 在室温下 PMMA 薄膜和 2-MeTHF。反过来，阳离子配合物 [Ir(C^N) 2 (dtb-bpy)][PF 6 ] 9 , 12a和12c (dtb-bpy = 4,4'-di- tert-丁基-2,2'-二吡啶）是黄绿色发射体，具有中等量子产率（0.24-0.32）。

  DOI：

  10.1039/d1dt04148g
• 作为产物：
  描述：

  9-乙基腺嘌呤 在 二碘甲烷 、 亚硝酸正戊酯 作用下， 反应 9.0h， 生成 9-ethyl-6-phenyl-9H-purine
  参考文献：
  名称：

  Arylation and heteroarylation of photochemically generated purinyl radicals

  摘要：

  DOI：

  10.1021/jo00144a023

文献信息

• Cobalt-Catalyzed C–H Cyanation of (Hetero)arenes and 6-Arylpurines with <i>N</i>-Cyanosuccinimide as a New Cyanating Agent
  作者：Amit B. Pawar、Sukbok Chang

  DOI：10.1021/ol503680d

  日期：2015.2.6

  A cobalt-catalyzed C–H cyanation reaction of arenes has been developed using N-cyanosuccinimide as a new electrophilic cyanating agent. The reaction proceeds with high selectivity to afford monocyanated products with excellent functional group tolerance. Substrate scope was found to be broad enough to include a wide range of heterocycles including 6-arylpurines.

  使用N-氰基琥珀酰亚胺作为新型的亲电子氰化剂，已开发出钴催化芳烃的CH氰化反应。反应以高选择性进行，得到具有优异的官能团耐受性的单氰酸酯化产物。发现底物的范围足够宽，可以包括包括6-芳基嘌呤在内的各种杂环。
• Facilitating Rh-Catalyzed C–H Alkylation of (Hetero)arenes and 6-Arylpurine Nucleosides (Nucleotides) with Electrochemistry
  作者：Qi-Liang Yang、Ying Liu、Lei Liang、Zhi-Hao Li、Gui-Rong Qu、Hai-Ming Guo

  DOI：10.1021/acs.joc.2c00391

  日期：2022.5.6

  An electrochemical approach to promote the ortho-C–H alkylation of (hetero)arenes via rhodium catalysis under mild conditions is described. This approach features mild conditions with high levels of regio- and monoselectivity that tolerate a variety of aromatic and heteroaromatic groups and offers a widely applicable method for late-stage diversification of complex molecular architectures including

  描述了一种在温和条件下通过铑催化促进（杂）芳烃的邻-C-H 烷基化的电化学方法。这种方法具有温和的条件，具有高水平的区域选择性和单选择性，可耐受各种芳香族和杂芳香族基团，并为复杂分子结构的后期多样化提供了一种广泛适用的方法，包括色氨酸、雌酮、地西泮、核苷和核苷酸。烷基硼酸和酯以及烷基三氟硼酸盐被证明是合适的偶联配对物。关键铑中间体的分离和机理研究为铑（III/IV 或 V）方案提供了强有力的支持。
• Microwave promoted palladium-catalyzed Suzuki–Miyaura cross-coupling reactions of 6-chloropurines with sodium tetraarylborate in water
  作者：Gui-Rong Qu、Peng-Yang Xin、Hong-Ying Niu、Xin Jin、Xiao-Ting Guo、Xi-Ning Yang、Hai-Ming Guo

  DOI：10.1016/j.tet.2011.09.082

  日期：2011.11

  An efficient method for the synthesis of 6-arylpurines (nucleosides) was developed via Suzuki–Miyaura cross-coupling reactions of 6-chloropurines (nucleosides) and sodium tetraarylborate in neat water (ethanol). The process gave good to high isolated yields within a short reaction time under microwave irradiated conditions.

  通过在净水（乙醇）中6-氯嘌呤（核苷）和四芳基硼酸钠的Suzuki-Miyaura交叉偶联反应，开发了一种合成6-芳基嘌呤（核苷）的有效方法。该方法在微波辐照条件下，在短的反应时间内获得了良好的高分离收率。
• Rhodium(III)-Catalyzed Synthesis of Diverse Fluorescent Polycyclic Purinium Salts from 6-Arylpurine Nucleosides and Alkynes
  作者：Qi-Liang Yang、Ying Liu、Yi-Rui Luo、Zhi-Hao Li、Hong-Wei Jia、Ya-Bo Fu、Gui-Rong Qu、Hai-Ming Guo

  DOI：10.1021/acs.orglett.2c01546

  日期：2022.6.17

  RhIII-catalyzed C–H activation/annulation of 6-arylpurine nucleosides with alkynes under mild reaction conditions. The resulting products displayed tunable photoluminescence covering most of the visible spectrum. Mechanistic insights delineated the rhodium catalyst’s mode of action. A purinoisoquinolinium-coordinated rhodium(I) sandwich complex was well characterized and identified as the key intermediate

  本文描述了一种有效的策略，用于在温和的反应条件下通过 Rh III催化的 6-芳基嘌呤核苷与炔烃的 C-H 活化/环化来组装具有广泛阴离子的功能化多环嘌呤盐库。所得产品显示出覆盖大部分可见光谱的可调光致发光。机械见解描绘了铑催化剂的作用方式。purinoisoquinolinium 配位的铑 (I) 夹层复合物被很好地表征并确定为关键中间体。
• Hydrogen-Bond-Assisted Controlled C–H Functionalization via Adaptive Recognition of a Purine Directing Group
  作者：Hyun Jin Kim、Manjaly J. Ajitha、Yongjae Lee、Jaeyune Ryu、Jin Kim、Yunho Lee、Yousung Jung、Sukbok Chang

  DOI：10.1021/ja4118472

  日期：2014.1.22

  We have developed the Rh-catalyzed selective C-H functionalization of 6-arylpurines, in which the purine moiety directs the C-H bond activation of the aryl pendant. While the first C-H amination proceeds via the N1-chelation assistance, the subsequent second C-H bond activation takes advantage of an intramolecular hydrogen-bonding interaction between the initially formed amino group and one nitrogen atom, either N1 or N7, of the purinyl part. Isolation of a rhodacycle intermediate and the substrate variation studies suggest that N1 is the main active site for the C-H functionalization of both the first and second amination in 6-arylpurines, while N7 plays an essential role in controlling the degree of functionalization serving as an intramolecular hydrogen-bonding site in the second amination process. This pseudo-Curtin-Hammett situation was supported by density functional calculations, which suggest that the intramolecular hydrogen-bonding capability helps second amination by reducing the steric repulsion between the first installed ArNH and the directing group.