9-methyl-6-phenyl-9H-purine | 83135-03-9

• 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-methyl-6-phenyl-9H-purine
• 英文别名: 9-methyl-6-phenylpurine
• CAS: 83135-03-9
• 化学式: C₁₂H₁₀N₄
• 分子量: 210.238
• InChiKey: CIJNHAUMIFXVIS-UHFFFAOYSA-N

物化性质

• 熔点：
  120 °C
• 沸点：
  415.7±37.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 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-methyl-6-phenyl-9H-purine 在 十二羰基三钌 、 PIFA 、 三异丙叉丙酮基膦 、 silver nitrate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 48.0h， 以43%的产率得到9-methyl-6-(3-nitrophenyl)purine
  参考文献：
  名称：

  机动设备3促进的钌催化元-6- Arylpurines的C-H硝化

  摘要：

  为了解决6-芳基嘌呤底物间位硝化的挑战，开发了一种通用的钌催化的间位CH硝化反应。使用空间受阻的膦配体对于催化效率至关重要，发现种类繁多的6-芳基嘌呤和核苷适用于该方法，从而以高收率提供了相应的完全间位硝化的产物。

  DOI：

  10.1021/acs.joc.8b00149
• 作为产物：
  描述：

  苯硼酸 在 palladium on activated charcoal 四(三苯基膦)钯 、 氢气 、 sodium carbonate 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 乙醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 20.0~90.0 ℃ 、400.0 kPa 条件下， 反应 11.0h， 生成 9-methyl-6-phenyl-9H-purine
  参考文献：
  名称：

  Synthesis and Biological Testing of Purine Derivatives as Potential ATP-Competitive Kinase Inhibitors

  摘要：

  On the basis of ATP adenine, a series of adenine and purine derivatives was prepared and tested for their ability to inhibit a spectrum of disease-related kinases. There has been scant research investigating the potential of cosubstrate derived kinase inhibitors for other kinases than CDKs. Our inhibitor design combined the purine system from the original cosubstrate ATP and phenyl moieties in order to explore possible interactions with the different regions of the ATP binding site in several disease-related protein kinases. There have been a number of hits for the assayed substances, which led us to conclude that the spectrum of compounds may prove to be a valuable tool kit for the evaluation of bonding and selectivity patterns for a wide variety of kinases.

  DOI：

  10.1021/jm0408767

文献信息

• Access to Branched Allylarenes via Rhodium(III)-Catalyzed C–H Allylation of (Hetero)arenes with 2-Methylidenetrimethylene Carbonate
  作者：Shang-Shi Zhang、Yi-Chuan Zheng、Zi-Wu Zhang、Shao-Yong Chen、Hui Xie、Bing Shu、Jia-Lin Song、Yan-Zhi Liu、Yao-Fu Zeng、Luyong Zhang

  DOI：10.1021/acs.orglett.1c01832

  日期：2021.8.6

  A rhodium(III)-catalyzed C–H allylation of (hetero)arenes by using 2-methylidenetrimethylene carbonate as an efficient allylic source has been developed for the first time. Five different directing groups including oxime, N-nitroso, purine, pyridine, and pyrimidine were compatible, delivering various branched allylarenes bearing an allylic hydroxyl group in moderate to excellent yields.

  首次开发了使用 2-亚甲基亚甲基碳酸酯作为有效烯丙基来源的铑（III）催化（杂）芳烃的 C-H 烯丙基化反应。五种不同的导向基团包括肟、N-亚硝基、嘌呤、吡啶和嘧啶是相容的，以中等至极好的产率提供带有烯丙基羟基的各种支链烯丙基芳烃。
• Iron-Catalyzed Highly para-Selective Difluoromethylation of Arenes
  作者：Wei-Tai Fan、Yuting Li、Dongjie Wang、Shun-Jun Ji、Yingsheng Zhao

  DOI：10.1021/jacs.0c09545

  日期：2020.12.9

  bond at either the meta or para position by only changing the catalyst system poses a significant challenge. We herein report the [Fe(TPP)Cl]-enabled, selective, C-H difluoromethylation of arenes using BrCF2CO2Et as the difluoromethylation source, which successfully altered the selectivity from the meta to the para position. A preliminary mechanistic study revealed the iron porphyrin complex not only

  仅通过改变催化剂体系在间位或对位直接官能化 CH 键是一项重大挑战。我们在此报告了使用 BrCF2CO2Et 作为二氟甲基化源的 [Fe(TPP)Cl] 启用的、选择性的、CH 二氟甲基化芳烃，这成功地改变了从间位到对位的选择性。初步的机理研究表明，铁卟啉配合物不仅激活了芳环，而且由于配体空间的影响，还诱导了对位选择性。
• Iron-Catalyzed Cross-Coupling Reactions
  作者：Alois Fürstner、Andreas Leitner、María Méndez、Helga Krause

  DOI：10.1021/ja027190t

  日期：2002.11.1

  and -CF(3) groups are compatible. The method also allows for consecutive cross-coupling processes in one pot, as exemplified by the efficient preparation of compound 12, and has been applied to the first synthesis of the cytotoxic marine natural product montipyridine 8. In contrast to the clean reaction of (hetero)aryl chlorides, the corresponding bromides and iodides are prone to a reduction of their

  简单的铁盐，如 FeCl(n)、Fe(acac)(n) (n = 2,3) 或 salen 络合物 4 被证明是高效、廉价、毒理学无害且环境友好的预催化剂，可用于许多交叉- 烷基或芳基格氏试剂、锌酸盐或有机锰物质与芳基和杂芳基氯化物、三氟甲磺酸盐甚至甲苯磺酸盐的偶联反应。原位制备的正式成分 [Fe(MgX)(2)] 的“无机格氏试剂”可能构成负责催化周转的传播物种，在许多情况下，即使在室温或室温以下，这种转化率也以前所未有的速度发生。由于反应条件异常温和，一系列官能团如酯、醚、腈、磺酸盐、磺酰胺、硫醚、缩醛、炔烃和 -CF(3) 基团是相容的。
• Direct Decarboxylative<i>Meta</i>-Selective Acylation of Arenes via an<i>Ortho</i>-Ruthenation Strategy
  作者：Kun Jing、Zhong-Yuan Li、Guan-Wu Wang

  DOI：10.1021/acscatal.8b03695

  日期：2018.12.7

  using Ru3(CO)12 as the catalyst and α-oxocarboxylic acids as the acylation source, featured broad substrate scope, good functional group tolerance, and high regioselectivity. Mechanistic studies demonstrated that a radical process and an 18e-octahedral ruthenium species were involved in this reaction. The present work provides a new strategy for the regioselective meta-acylation reactions and will

  通过钌催化的邻位金属化策略，可以建立多种芳烃的直接脱羧间选择性C–H酰化反应。该方法以Ru 3（CO）12为催化剂，α-氧代羧酸为酰化源，具有较宽的底物范围，良好的官能团耐受性和较高的区域选择性。机理研究表明，该反应涉及自由基过程和18e-八面体钌物种。目前的工作为区域选择性间酰化反应提供了一种新的策略，并将成为药物和材料科学发展的有力工具。
• 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。