9-benzyl-6-(p-tolyl)-9H-purine

• 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-(p-tolyl)-9H-purine
• 英文别名: 9-Benzyl-6-(4-methylphenyl)purine；9-benzyl-6-(4-methylphenyl)purine
• 化学式: C₁₉H₁₆N₄
• 分子量: 300.363
• InChiKey: YVOJDRJTQXAZNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 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-benzyl-6-(p-tolyl)-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-methylphenol
  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：

  溴甲苯 在 四(三苯基膦)钯 、 sodium carbonate 、 potassium carbonate 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 12.33h， 生成 9-benzyl-6-(p-tolyl)-9H-purine
  参考文献：
  名称：

  N-Allylbenzimidazole as a strategic surrogate in Rh-catalyzed stereoselective trans-propenylation of aryl C(sp²)–H bond

  摘要：

  报道了一种使用N-烯丙基苯并咪唑作为烯丙胺类似物的配体，通过Rh催化的C(sp2)-H烯丙基化反应。

  DOI：

  10.1039/d2cc06048e

文献信息

• 一种高效氮化试剂及其应用
  申请人：北京大学

  公开号：CN112574054B

  公开（公告）日：2022-10-14

  本发明公开了一种高效氮化试剂及其应用。所述的氮化试剂包括氮氧化物、活性剂、还原剂及有机溶剂。应用该氮化试剂可生产酰胺及腈等含氮化合物，并且方法条件简单、废弃物排放量少、反应设备简单。
• 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。
• Cp*Co^III-catalyzed directed C–H trifluoromethylthiolation of 2-phenylpyridines and 6-arylpurines
  作者：Misaki Yoshida、Kentaro Kawai、Ryo Tanaka、Tatsuhiko Yoshino、Shigeki Matsunaga

  DOI：10.1039/c7cc03072j

  日期：——

  Cp*Co^III-catalyzed directed C–H trifluoromethylthiolation using N-trifluoromethylthiodibenzenesulfonimide as an electrophilic SCF₃ source is described.

  Cp*Co^III催化的定向C–H三氟甲硫基化反应，使用N-三氟甲硫基二苯磺酰亚胺作为亲电性SCF₃源进行。
• 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。
• Palladium-catalyzed C–H bond functionalization of C6-arylpurines
  作者：Hai-Ming Guo、Wei-Hao Rao、Hong-Ying Niu、Li-Li Jiang、Ge Meng、Jia-Jia Jin、Xi-Ning Yang、Gui-Rong Qu

  DOI：10.1039/c1cc11135c

  日期：——

  A highly regioselective Pd-catalyzed C_Ar–H bond activation method was developed for the modification of purines (nucleosides) with different functional groups by using purine as a directing group. This approach provides a new access to a variety of functionalized purines (nucleosides).

  开发了一种高度区域选择性的Pd催化的C_Ar–H键活化方法，用于利用嘌呤作为定向基团对带有不同功能基团的嘌呤（核苷）进行改性。这种方法为多种官能化的嘌呤（核苷）提供了新的途径。