3-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-7H-purin-7-yl)propanenitrile | 1811-38-7

• 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: 3-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-7H-purin-7-yl)propanenitrile
• 英文别名: 1,3-dimethyl-7H-xanthine-7-propanenitrile；3-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-yl)-propionitrile；3-(1,3-Dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-purin-7-yl)-propionitril；7-(2-Cyano-ethyl)-theophyllin；7-Cyanaethyl-theophyllin；3-(1,3-dimethyl-2,6-dioxopurin-7-yl)propanenitrile
• CAS: 1811-38-7
• 化学式: C₁₀H₁₁N₅O₂
• mdl: MFCD01694175
• 分子量: 233.23
• InChiKey: KAVJVVVIFOIZKM-UHFFFAOYSA-N

物化性质

• 熔点：
  160 °C
• 沸点：
  525.9±56.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  82.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-7H-purin-7-yl)propanenitrile 在 甲醇 、 钴 作用下， 100.0 ℃ 、9.81 MPa 条件下， 生成 7-(γ-Aminopropyl)theophyllin
  参考文献：
  名称：

  Process for the manufacture of xanthine derivatives

  摘要：

  公开号：

  US02761862A1
• 作为产物：
  描述：

  茶碱 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 5.0h， 生成 3-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-7H-purin-7-yl)propanenitrile
  参考文献：
  名称：

  N 7-Tosyltheophylline (TsTh): A Highly Efficient Reagent for the One-Pot Synthesis of N 7-Alkyltheophyllines from Alcohols

  摘要：

  A convenient and highly efficient one-pot N-alkylation of theophylline from alcohols via N-7-tosyltheophylline (TsTh) is described. In this protocol, the treatment of primary and/or secondary alcohols with a mixture of TsTh and 1,8-diazabicyclo[5.4.0]undec-7-ene in refluxing acetonitrile affords the corresponding N-7-alkyltheophylline in good to excellent yields; the reaction was optimized for solvent and base. This methodology is highly efficient for various structurally diverse primary and secondary alcohols. A plausible mechanism for the one-pot N-alkylation of theophylline with alcohols via TsTh has been suggested.

  DOI：

  10.1055/s-0033-1341026

文献信息

• Highly efficient protocol for one-pot N-alkylation of nucleobases using alcohols in bmim[Br]: a rapid route to access acyclic nucleosides
  作者：Mohammad Navid Soltani Rad、Somayeh Behrouz、Elham Zarenezhad、Narjes Kaviani

  DOI：10.1007/s13738-015-0633-9

  日期：2015.9

  Highly efficient protocol for one-pot N-alkylation of nucleobases using alcohol in ionic liquid media as a straightforward route to access acyclic nucleoside was described. In this protocol purine, pyrimidine as well as azole derivatives underwent the N-alkylation reaction with primary or secondary alcohols using TsCl/TEA/K2CO3 in bmim[Br] to afford the products in good-to-excellent yields. The influence of factors in this method including the type of ionic liquid, base and sulfonating agents was discussed. The current method showed an appropriate selectivity in reaction with primary alcohols in comparison with secondary alcohols. This protocol is mild, safe and easy to apply; moreover, it is quite compatible with eco-friendly and green chemistry protocols, since the exploitation of toxic and hazardous materials such as DMF and alkyl halides has been prevented.

  描述了一种在离子液体介质中使用醇对核苷碱基进行高效一锅法N-烷基化的协议，作为获取无环核苷的直接途径。在此协议中，嘌呤、嘧啶以及唑类衍生物与一级或二级醇在TsCl/TEA/K2CO3于bmim[Br]中进行N-烷基化反应，得到良好至极佳产率的产物。讨论了该方法中包括离子液类型、碱和磺化剂等因素的影响。当前方法在反应中对一级醇显示出适当的优先选择性，相较于二级醇。该协议温和、安全且易于应用；此外，由于避免了使用如DMF和烷基卤等有毒及危险材料，它与生态友好和绿色化学协议高度兼容。
• Cu/Graphene/Clay Nanohybrid: A Highly Efficient Heterogeneous Nanocatalyst for Synthesis of New 5-Substituted-1<i>H</i>-Tetrazole Derivatives Tethered to Bioactive<i>N</i>-Heterocyclic Cores
  作者：Mohammad Navid Soltani Rad、Somayeh Behrouz、Vahid Sadeghi Dehchenari、S. Jafar Hoseini

  DOI：10.1002/jhet.2591

  日期：2017.1

  bioactive N‐heterocyclic cores were synthesized through [3 + 2] cycloaddition reactions between alkyl nitriles (RCN) and NaN3 in the presence of Cu/aminoclay/reduced graphene oxide nanohybrid (Cu/AC/r‐GO nanohybrid) as a heterogeneous nanocatalyst in water/i‐PrOH (50:50, V/V) media at reflux condition. The influence of factors on a sample reaction including solvent type, temperature, and catalyst amount

  在存在铜/氨基粘土/还原氧化石墨烯纳米杂化物（铜）的情况下，通过烷基腈（RCN）和NaN 3之间的[3 + 2]环加成反应，合成了一系列具有生物活性N杂环核的5位取代的1 H-四唑。/ AC / R-GO纳米杂化物）作为在水中的纳米催化剂的异构/我‐PrOH（50:50，V / V）介质在回流条件下。讨论了因素对样品反应的影响，包括溶剂类型，温度和催化剂用量。该当前协议具有许多优点，包括价格便宜，对环境无害，基材范围广，产率高以及易于处理。该协议中使用的Cu / AC / r-GO是一种低成本催化剂，被证明具有相当大的化学和热稳定性。这种非吸湿性催化剂可以轻松回收，再利用和存储，以进行许多连续的反应，而不会显着降低反应活性。
• Synthesis, Antifungal Evaluation and Molecular Docking Studies of Some Tetrazole Derivatives
  作者：Mohammad Hosein Afsarian、Mojtaba Farjam、Elham Zarenezhad、Somayeh Behrouz、Mohammad Navid Soltani Rad

  DOI：10.17344/acsi.2019.4992

  日期：——

  A facile and simple protocol for the [3+2] cycloaddition of alkyl nitriles (RCN) with sodium azide (NaN 3 ) in the presence of copper bis(diacetylcurcumin) 1,2-diaminobenzene Schiff base complex, SiO 2 -[Cu-BDACDABSBC] as a heterogeneous catalyst in the presence of ascorbic acid and a solution of water/ i -PrOH (50:50, V/V) media at reflux condition is described. The supported catalyst was prepared

  在铜双（二乙酰姜黄素）1,2-二氨基苯席夫碱铜配合物SiO 2-[Cu-描述了在抗坏血酸和水/ i-PrOH（50:50，V / V）介质在回流条件下存在下作为非均相催化剂的[BDACDABSBC]。通过将双（二乙酰姜黄素）铜1,2-二氨基苯希夫碱配合物[Cu-BDACDABSBC]固定在硅胶上制备负载型催化剂。该络合物具有高选择性，催化活性和可回收性。该过程的显着特征是高产量，广泛的基材范围以及简单而有效的后处理过程。根据这种综合方法，合成了具有生物活性N-杂环核心的5取代1 H-四唑的优异收率。筛选了标题化合物的体外抗真菌活性，以对抗各种致病性真菌菌株，例如涉及白色念珠菌，光滑念珠菌，克鲁氏梭菌，近生念珠菌的念珠菌以及由烟曲霉和烟曲霉组成的丝状真菌如曲霉。黄曲霉 讨论了一种最有效的抗真菌化合物的分子对接分析。对接研究确定了最有效的化合物与分枝杆菌P450DM的活性位点之间的显着相互作用
• Michael Adducts in the Regioselective Synthesis of N-Substituted Azoles
  作者：András Horváth

  DOI：10.1055/s-1995-4054

  日期：1995.9

  Michael adducts of azoles (4-phenyl-, 4-methyl- and 4-nitroimidazole, 4-methylbenzimidazole, 1,2,4-triazole and theophylline) are shown to be valuable substrates for obtaining the N-substituted derivatives of the parent heterocycles by a quaternization-Hofmann elimination sequence. The effectiveness of the procedure is dependent on the regiochemical outcome of the first, N-protective step, i.e. the Michael addition. By choosing the appropriate Michael acceptor, alkylating agent and deprotection conditions, the thermodynamically less stable regioisomers of N-substituted azoles have been obtained in high yields.

  米哈伊尔加成物的偶氮物（4-苯基、4-甲基和4-硝基咪唑、4-甲基苯并咪唑、1,2,4-三唑和茶碱）被证明是获得母体杂环的N-取代衍生物的重要底物，这一过程通过一个季铵化-霍夫曼消除序列实现。该程序的有效性取决于第一个N保护步骤（即迈克尔加成）的区域化学结果。通过选择适当的迈克尔受体、烷基化试剂和去保护条件，可以以高产率获得N-取代偶氮物的热力学不太稳定的区域异构体。
• An Efficient Protocol for Facile Synthesis of New 5-Substituted-1<i>H</i>-Tetrazole Derivatives Using Copper-Doped Silica Cuprous Sulfate (CDSCS) as Heterogeneous Nano-Catalyst
  作者：Mohammad Navid Soltani Rad

  DOI：10.5935/0103-5053.20160138

  日期：——

  A facile and highly efficient protocol for synthesis of new 5-substituted-1H-tetrazoles derivatives using copper-doped silica cuprous sulfate (CDSCS) is described. In this method, the cycloaddition reaction of sodium azide with structurally diverse nitriles involving bioactive N-heterocyclic cores exploiting CDSCS in refluxing H2O/i-PrOH (1:1, v/v) furnishes the corresponding 5-substituted1H-tetrazoles in good to excellent yields (up to 93%). The influence of parameters effective in progress of reaction including solvent type, temperature and catalyst was studied and discussed. In this protocol, CDSCS was proved to be an efficient heterogeneous nano-catalyst to easily achieve the new tetrazole derivatives. The advantages of CDSCS in current protocol known are its cheapness, thermal and chemical stability, ease of recyclability and reusability for several consecutive runs without significant decline in its reactivity.