9-benzyl-6-(4-methoxyphenyl)-9H-purine | 83135-05-1

• 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-benzyl-6-(4-methoxyphenyl)-9H-purine
• 英文别名: 9-benzyl-6-(p-methoxyphenyl)purine；9-Benzyl-6-(4-methoxyphenyl)purine
• CAS: 83135-05-1
• 化学式: C₁₉H₁₆N₄O
• 分子量: 316.362
• InChiKey: GVAHOPZTSLZXAP-UHFFFAOYSA-N

物化性质

• 熔点：
  158-160 °C
• 沸点：
  547.5±60.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  9-benzyl-6-(4-methoxyphenyl)-9H-purine 在 sodium methylate 、 palladium diacetate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 27.0h， 生成 2-(9-benzyl-9H-purin-6-yl)-5-methoxyphenol
  参考文献：
  名称：

  Purinyl N1-Directed Aromatic C–H Oxidation in 6-Arylpurines and 6-Arylpurine Nucleosides

  摘要：

  Palladium-catalyzed C-H bond activation and oxidation of C6 arylpurines as well as C6 arylpurine nucleosides can be accomplished using Pd(OAc)(2)/PhI(OAc)(2) in CH3CN. Despite the presence of four nitrogen atoms in the purine moiety as well as the polyoxygenated saccharide and a labile glycosidic bond in the nucleosides, these reactions can be effectively conducted. Notably, the generally more labile 2'-deoxyribonucleosides also undergo reaction. The reaction conditions can be tuned to yield either monoacetoxylated or diacetoxylated products predominantly. In the course of these investigations, a dimeric Pe(II)-containing cyclopalladated C6 naphthylpurine derivative has been obtained and crystallographically characterized. This compound is competent in catalyzing the oxidization with PhI(OAc)(2), indicating its plausible intermediacy in the chemistry. The X-ray structure of a monoacetoxylated product from this reaction has also been obtained.

  DOI：

  10.1021/jo4008282
• 作为产物：
  描述：

  6-氯嘌呤 在 四(三苯基膦)钯 lithium 、 potassium carbonate 、 zinc dibromide 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.0h， 生成 9-benzyl-6-(4-methoxyphenyl)-9H-purine
  参考文献：
  名称：

  钯催化的6-卤尿烷与有机锡和有机锌试剂偶联

  摘要：

  N -9和N -7苄基化的6-卤尿烷易于参与钯催化的有机锡和有机锌衍生物的交叉偶联反应

  DOI：

  10.1016/s0040-4020(01)85540-x

文献信息

• Recyclable Ruthenium Catalyst for Distal <i>meta</i> ‐C−H Activation
  作者：Isaac Choi、Valentin Müller、Yanhui Wang、Kai Xue、Rositha Kuniyil、Loren B. Andreas、Volker Karius、Johan G. Alauzun、Lutz Ackermann

  DOI：10.1002/chem.202003622

  日期：2020.11.26

  unprecedented hybrid‐ruthenium catalysis for distal meta‐C−H activation. The hybrid‐ruthenium catalyst was recyclable, as was proven by various heterogeneity tests, and fully characterized with various microscopic and spectroscopic techniques, highlighting the physical and chemical stability. Thereby, the hybrid‐ruthenium catalysis proved broadly applicable for meta‐C−H alkylations of among others purine‐based

  我们公开了前所未有的用于远端元-C-H激活的混合钌催化。各种非均质性测试证明，杂化钌催化剂是可回收的，并通过各种显微和光谱技术进行了充分表征，突出了物理和化学稳定性。因此，杂化钌催化被证明广泛适用于基于嘌呤的核苷和天然产物缀合物的间位-C-H烷基化。此外，通过可见光照射的元-C-H激活以及对位选择性C-H激活进一步反映了其多功能性。
• Pd^II -Catalyzed Purine-Directed Ortho Nitration of 6-Arylpurines by C(sp² )-H Activation: A Practical Approach to Synthesize 6-(2-Nitroaryl)-Purine Derivatives
  作者：Quan Gou、Wenxi Li、Qingsheng Zhao、Jia Xie、Ping Luo、Guang Cao、Suiyun Chen、Jun Qin

  DOI：10.1002/ejoc.201800567

  日期：2018.8.15

  6‐(2‐Nitroaryl)‐purine can be obtained through PdII‐catalyzed C(sp2)–H activation of 6‐arylpurines in the presence of tBuONO/O2. The purine substituent acts as an ortho directing group for the nitration.

  在t BuONO / O 2存在下，Pd II催化6-芳基嘌呤的C（sp 2）-H活化可制得6-（2-硝基芳基）-嘌呤。嘌呤取代基充当硝化的邻位导向基团。
• Cross-Coupling Reactions of Halopurines with Aryl- and Alkyltrifluoro­borates; The Scope and Limitations in the Synthesis of Modified Purines
  作者：Michal Hocek、Zbyněk Hasník、Radek Pohl

  DOI：10.1055/s-0028-1088038

  日期：2009.4

  The scope and limitations of the use of the palladium-catalyzed cross-coupling reactions of diverse alkyl- and aryltrifluoroborates with halopurines have been studied. While aryl- and hetaryltrifluoroborates reacted readily with both 6-chloropurines and 8-bromoadenines to give the corresponding 6- or 8-aryl derivatives in high yields, the alkyltrifluoroborates were much less reactive and, even after

  已经研究了使用钯催化的多种烷基-和芳基三氟硼酸酯与卤代扁桃酸酯的交叉偶联反应的范围和局限性。芳基和杂芳基三氟硼酸酯容易与6-氯嘌呤和8-溴代丁烯反应，以高收率得到相应的6-或8-芳基衍生物，而三氟硼酸烷基酯的反应性低得多，即使经过充分优化，也只能得到甲基和环丙基三氟硼酸酯。所需的烷基化嘌呤产率适中，而其他烷基，二烷基氨基甲基和乙氧基羰基乙基三氟硼酸酯则未发生任何反应。 嘌呤-交叉偶联反应-有机三氟硼酸盐-钯-膦配体
• 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(<scp>iii</scp>)-catalyzed CF₃-carbenoid C–H functionalization of 6-arylpurines
  作者：Daria V. Vorobyeva、Mikhail M. Vinogradov、Yulia V. Nelyubina、Dmitry A. Loginov、Alexander S. Peregudov、Sergey N. Osipov

  DOI：10.1039/c8ob00645h

  日期：——

  An efficient method for the CF3-carbenoid C–H functionalization of 6-arylpurines has been developed. This protocol uses readily available methyl 3,3,3-trifluoro-2-diazopropionate as a cross-coupling partner and proceeds smoothly under chelation-controlled Rh(III) catalysis. The reactions provide the corresponding carbene insertion products with high regioselectivity within a few hours and allow the

  已经开发出一种有效的方法，用于将6-芳基嘌呤的CF 3-类胡萝卜素C–H功能化。该协议使用易于获得的3,3,3-三氟-2-重氮丙酸甲酯作为交叉偶联伴侣，并在螯合控制的Rh（III）催化下顺利进行。该反应在数小时内为相应的卡宾插入产物提供了高区域选择性，并允许将CF 3和羧酸盐功能引入生物学上重要的嘌呤分子，包括核苷衍生物。