1,3-dimethyl-7-phenethyl-1H-purine-2,6(3H,7H)-dione | 374545-12-7

• 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: 1,3-dimethyl-7-phenethyl-1H-purine-2,6(3H,7H)-dione
• 英文别名: 1,3-dimethyl-7-(2-phenylethyl)-3,7-dihydro-1H-purine-2,6-dione；1,3-dimethyl-7-(2-phenylethyl)purine-2,6-dione
• CAS: 374545-12-7
• 化学式: C₁₅H₁₆N₄O₂
• 分子量: 284.318
• InChiKey: XPIOKRFUVIVDGS-UHFFFAOYSA-N

物化性质

• 沸点：
  520.0±52.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  58.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 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 3.0h， 生成 1,3-dimethyl-7-phenethyl-1H-purine-2,6(3H,7H)-dione
  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。
• One-pot protocol for N-alkylation of purine, pyrimidine and azole derivatives via alcohols using Ph 3 P/I 2 : simple route for carboacyclic nucleoside synthesis
  作者：Mohammad Navid Soltani Rad、Faezeh Soleimani

  DOI：10.1016/j.tet.2016.06.069

  日期：2016.8

  efficient synthetic protocol for the one-pot N-alkylation of nucleobases and their related N-heterocycles via alcohols utilizing the combination of PPh3 and I2 is reported. In this protocol purine, pyrimidine and azole derivatives underwent the N-alkylation reaction with diverse primary alcohols using Ph3P/I2 in the presence of Et3N-K2CO3 in anhydrous DMF to give the N-alkyl adducts (carboacyclic nucleosides)

  据报道，利用PPh 3和I 2的组合，通过醇进行一锅N-烷基化核碱基及其相关的N-杂环的简单有效的合成方案。在这个协议中嘌呤，嘧啶和吡咯衍生物经历与使用pH不同的伯醇的N-烷基化反应3 P / I 2的Et的存在3 N-K 2 CO 3在无水DMF，得到Ñ-烷基加合物（碳环核苷）的收率很高（高达90％）。讨论了该反应中一些参数的影响，包括溶剂类型，碱，试剂和温度。此外，该方案已证明对二醇中伯羟基相对于仲羟基具有良好的选择性。
• [EN] SMALL MOLECULE ALDEHYDE DEHYDROGENASE INHIBITORS AND METHODS OF USE THEREOF<br/>[FR] PETITES MOLÉCULES INHIBITEURS DES ALDÉHYDE-DÉSHYDROGÉNASES ET LEURS MÉTHODES D'UTILISATION
  申请人：US HEALTH

  公开号：WO2016086008A1

  公开（公告）日：2016-06-02

  Described herein are compounds, salts and solvates of the formula (I). Certain compounds of formula (I) are potent and selective inhibitors of aldehyde dehydrogenases (ALDH), a family of enzymes that play a critical role in detoxification of various cytotoxic xenogenic and biogenic aldehydes. As such, compounds of formula (I) are useful for treating disorders in which ALDH inhibition is needed, including cancer, inflammatory disorders, and obesity. The disclosure also includes compositions, and methods for inhibiting aldehyde dehydrogenases (ALDH).

  本发明涉及公式(I)的化合物、盐和溶剂化物。公式(I)的某些化合物是醛脱氢酶(ALDH)的强效和选择性抑制剂，ALDH是一类在解毒各种细胞毒性的异生物质和生物源性醛方面发挥关键作用的酶。因此，公式(I)的化合物可用于治疗需要ALDH抑制的疾病，包括癌症、炎症性疾病和肥胖。本发明还包括用于抑制醛脱氢酶(ALDH)的组合物和方法。
• Triphenylphosphine-free approach for one-pot N-alkylation of purine, pyrimidine, and azole derivatives with alcohols using P2O5/KI: A facile and selective route to access carboacyclic nucleosides
  作者：Somayeh Behrouz、Mohammad Navid Soltani Rad、Samira Ahmadi

  DOI：10.1016/j.tet.2019.130499

  日期：2019.9

  A facile, selective, and mild synthetic approach for one-pot N-alkylation of nucleobases and other related N-heterocycles via alcohols, using a mixture of P2O5 and KI is described. The reaction of structurally diverse purines, pyrimidines, and/or azoles with primary alcohols with the use of P2O5/KI and basic mixture of Et3N/K2CO3 in refluxing DMF affords the corresponding N-alkyl derivatives (carboacyclic

  描述了一种使用P 2 O 5和KI的混合物通过醇通过一锅法对核碱基和其他相关N-杂环进行N-烷基化的简便，选择性和温和的合成方法。使用P 2 O 5 / KI和Et 3 N / K 2 CO 3的碱性混合物，使结构不同的嘌呤，嘧啶和/或唑与伯醇反应在回流中，DMF以良好至合理的产率得到相应的N-烷基衍生物（碳环核苷）。评估了包括溶剂，碱，温度和底物/试剂比率的不同参数对反应进程的影响。仲和叔醇不能与核碱基反应。当前方案的主要优点是形成水溶性副产物，其中提供了简单的后处理和纯化过程。
• Aminodealkenylation: Ozonolysis and copper catalysis convert C(sp ³ )–C(sp ² ) bonds to C(sp ³ )–N bonds
  作者：Zhiqi He、Jose Antonio Moreno、Manisha Swain、Jason Wu、Ohyun Kwon

  DOI：10.1126/science.adi4758

  日期：2023.8.25

  alkene π bond amination. In contrast, analogous functionalization of the adjacent C(sp 3 )–C(sp 2 ) σ bonds is much rarer. Here we report how ozonolysis and copper catalysis under mild reaction conditions enable alkene C(sp 3 )–C(sp 2 ) σ bond–rupturing cross-coupling reactions for the construction of new C(sp 3 )–N bonds. We have used this unconventional transformation for late-stage modification of

  烯烃π键胺化已经投入了大量精力。相比之下，相邻 C（sp 3 ）–C（sp 2 ） σ键的类似官能化要罕见得多。在这里，我们报道了在温和反应条件下的臭氧分解和铜催化如何使烯烃 C（sp 3 ）-C（sp 2 ） σ键破裂交叉偶联反应能够构建新的 C（sp 3 ）-N 键。我们已经将这种非常规转化用于激素、药物试剂、肽和核苷的后期修饰。此外，我们还将大量可用的萜烯和萜类化合物与亲氮试剂偶联，以获得人工萜类生物碱和复杂的手性胺。此外，我们还应用了一种商品化学品 α-甲基苯乙烯作为甲基化试剂，在一个合成步骤中直接从经典核苷制备甲基化核苷。我们的机理研究涉及一个不寻常的铜离子对合作过程。