9-benzyl-6-(methoxy)-9H-purine | 6937-62-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 9-benzyl-6-(methoxy)-9H-purine
• 英文别名: 9-benzyl-6-methoxy-9H-purine；N9-benzyl-6-methoxypurine；6-methoxy-9-benzylpurine；9-benzyl-6-methoxypurine；9-benzyl-6-methoxy-9H-purine；6-Methoxy-9-benzyl-9H-purin
• CAS: 6937-62-8
• 化学式: C₁₃H₁₂N₄O
• 分子量: 240.264
• InChiKey: TYHGYCWDNURLRY-UHFFFAOYSA-N

物化性质

• 熔点：
  114-116 °C(Solv: heptane (142-82-5))
• 沸点：
  444.3±55.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 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-(methoxy)-9H-purine 在 二异丁基氢化铝 、 Glauber's salt 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 2.0h， 以65%的产率得到9-benzyl-6-methoxy-7,8-dihydropurine
  参考文献：
  名称：

  Selective Synthesis of 7-Substituted Purines via 7,8-Dihydropurines

  摘要：

  A simple and efficient protocol for the preparation of 7-substituted purines is described. 6- and 2,6-Dihalopurines were N-9-tritylated and then transformed to 7,8-dihydropurines by DIBAL-H. Subsequent N-7-alkylation followed by N-9-trityl deprotection with trifluoroacetic acid was accompanied by spontaneous reoxidation, which led to the 7-substituted purines at 55-88% overall isolated yields.

  DOI：

  10.1021/ol1025525
• 作为产物：
  描述：

  6-氯嘌呤 在 sodium 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.25h， 生成 9-benzyl-6-(methoxy)-9H-purine
  参考文献：
  名称：

  8-Bromination of 2,6,9-trisubstituted purines with pyridinium tribromide

  摘要：

  2,6,9-Trisubstituted purines are brominated in high yields using pyridinium tribromide as the brominating reagent. This procedure works excellently for electron-rich purines having electron-donating substituents at the 2- and 6-positions. The use of pyridinium tribromide, a crystalline alternative to elemental bromine, improves the bromination procedure for this type of substrate as the reagent is easy to handle and the work-up and purification procedures are simplified. (C) 2014 The Authors. Published by Elsevier Ltd.

  DOI：

  10.1016/j.tetlet.2014.03.084

文献信息

• CuI Controlled C–C and C–N Bond Formation of Heteroaromatics through C(sp³)–H Activation
  作者：Ran Xia、Hong-Ying Niu、Gui-Rong Qu、Hai-Ming Guo

  DOI：10.1021/ol302640e

  日期：2012.11.2

  A new method for C–C and C–N bond formation of heteroaromatics and C(sp3)–H alkanes was developed with high regioselectivity. The reaction occurred on C8 to give 8-cylcoakylpurines by C–C bond formation only promoted by tBuOOtBu, while it occurred on the amino group to give N6-alkylated purines by C–N bond formation when 2 equiv of CuI were added. A reaction mechanism was also proposed based on our

  具有高区域选择性的杂芳烃和C（sp 3）-H烷烃的C–C和C–N键形成的新方法得到了发展。该反应发生在C8上，仅通过t BuOO t Bu促进了通过C–C键形成的8烷基甲酰基嘌呤，而当氨基当上，当2当量的CuI为2时，通过C–N键的形成产生了N 6烷基化的嘌呤。添加。根据我们的初步实验数据，还提出了一种反应机理。
• C–H Amination of Purine Derivatives via Radical Oxidative Coupling
  作者：Zheng Luo、Ziyang Jiang、Wei Jiang、Dongen Lin

  DOI：10.1021/acs.joc.8b00066

  日期：2018.4.6

  An oxidative coupling reaction between purines and alkyl ethers/benzyl compounds was developed to synthesize a series of N9 alkylated purine derivatives using n-Bu4NI as a catalyst and t-BuOOH as an oxidant. This protocol uses commercially available, inexpensive catalysts and oxidants and has a wide range of substrates with a simple operation.

  开发了嘌呤与烷基醚/苄基化合物之间的氧化偶联反应，以n -Bu 4 NI为催化剂，t -BuOOH为氧化剂，合成了一系列N9烷基化的嘌呤衍生物。该方案使用可商购的，廉价的催化剂和氧化剂，并具有操作简单的多种底物。
• Nickel catalyzed alkylation of N-aromatic heterocycles with Grignard reagents through direct C–H bond functionalization
  作者：Peng-Yang Xin、Hong-Ying Niu、Gui-Rong Qu、Rui-Fang Ding、Hai-Ming Guo

  DOI：10.1039/c2cc32396f

  日期：——

  A novel protocol for nickel-catalyzed direct sp2 C–H bond alkylation of N-aromatic heterocycles has been developed. This new reaction proceeded efficiently at room temperature using a Grignard reagent as the coupling partner. This approach provides new access to a variety of alkylated N-aromatic heterocycles which are potentially of great importance in medicinal chemistry.

  一种新的协议已被开发用于镍催化的N-芳香族杂环直接sp² C–H键烷基化反应。该反应在室温下以格里尼亚试剂作为耦合伙伴高效进行。这种方法为获取各种烷基化的N-芳香族杂环提供了新的途径，这些化合物在药物化学中可能具有重要价值。
• 一种C8-杂环烷基化嘌呤核苷类似物及其合成 方法
  申请人：河南科技学院

  公开号：CN104478883B

  公开（公告）日：2016-04-06

  本发明提供了一种原料便宜易得、反应条件温和、反应步骤少、高效C-H活化合成C8位杂环烷基化核苷类似物的方法，立足于解决此类化合物合成过程中原料昂贵、过程复杂、反应条件苛刻的问题，为核苷类药物的合成及应用提供参考价值，为新型抗病毒及抗肿瘤药物的研究提供原料。同时为其他核苷及其类似物的杂烷基化提供有效方法，并具有广泛的工业应用前景。
• Synthesis of C8-alkyl-substituted purine analogues by direct alkylation of 8- H purines with tetrahydrofuran catalyzed by CoCl 2 ·6H 2 O
  作者：Hong-Ying Niu、Ling-Yun Su、Shi-Xia Bai、Jian-Ping Li、Xi-Lan Feng、Hai-Ming Guo

  DOI：10.1016/j.cclet.2016.06.009

  日期：2017.1

  C8-Alkyl-substituted purine analogues were synthesized through direct alkylation of 8-H purine with tetrahydrofuran in the presence of Co catalyst in one step. The reactions gave a series of novel C8-oxygen heterocyclic alkyl purine compounds in good yields under mild reaction conditions by the readily available alkylating reagents, providing a complementary route to the classical coupling reactions

  在Co催化剂的存在下，一步一步通过用四氢呋喃将8-H嘌呤直接烷基化来合成C8-烷基取代的嘌呤类似物。通过容易获得的烷基化试剂，该反应在温和的反应条件下以高收率得到了一系列新颖的C8-氧杂环烷基嘌呤化合物，为经典的偶联反应提供了一条补充途径，用于合成C8-烷基取代的嘌呤类似物。