2-(2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)ethyl)isoindoline-1,3-dione | 221456-26-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-(2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)ethyl)isoindoline-1,3-dione
• 英文别名: 2-{2-[2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl]ethyl}isoindoline-1,3-dione；1-(2-phthalimidoethyl) uracil；1-(2-phthalimidoethyl)uracil；2-[2-(2,4-Dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-ethyl]-isoindole-1,3-dione；2-[2-(2,4-dioxopyrimidin-1-yl)ethyl]isoindole-1,3-dione
• CAS: 221456-26-4
• 化学式: C₁₄H₁₁N₃O₄
• 分子量: 285.259
• InChiKey: XHEVANCHHPZITL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  86.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)ethyl)isoindoline-1,3-dione 在 正丁胺 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 72.0h， 生成 1-(2-氨基乙基)尿嘧啶
  参考文献：
  名称：

  碳纳米管–核碱基杂化物：尿嘧啶修饰的单壁碳纳米管的纳米环

  摘要：

  单壁碳纳米管（SWCNT）已与尿嘧啶核碱基共价官能化。通过使用互补光谱学和显微技术（包括固态NMR光谱学）对杂种进行了表征。经AFM和TEM观察，尿嘧啶功能化的SWCNT能够自组装成直径为50-70 nm的规则纳米环。AFM显示，环的高度和厚度不一致，这表明它们可能是由单独的CNT束形成的。形成纳米环的最简单模型可能涉及两束CNT，它们通过在CNT两端的尿嘧啶-尿嘧啶碱基配对相互相互作用。可以设想将这些纳米环用于先进电子电路的开发。

  DOI：

  10.1002/chem.201100312
• 作为产物：
  描述：

  potassium phtalimide 在 potassium carbonate 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 2-(2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)ethyl)isoindoline-1,3-dione
  参考文献：
  名称：

  Das, Biplab Kumar; Shibata, Norio; Takeuchi, Yoshio, Journal of the Chemical Society. Perkin Transactions 1 (2001), 2002, vol. 2, # 2, p. 197 - 206

  摘要：

  DOI：

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 Synthesis of N-Alkyl Purine, Pyrimidine and Azole Derivatives from Alcohols using Ph3P/CCl4: A Rapid Route to Carboacyclic Nucleoside Synthesis
  作者：Mohammad Soltani Rad、Ali Khalafi-Nezhad、Somayeh Behrouz、Zeinab Asrari、Marzieh Behrouz、Zohreh Amini

  DOI：10.1055/s-0029-1216887

  日期：2009.9

  A facile and efficient method for one-pot N-alkylation of nucleobases and azole derivatives from alcohols using triphenylphosphine in carbon tetrachloride is described. In this method, treatment of alcohols with a mixture of triphenylphosphine, carbon tetrachloride, nucleobase or azole derivatives and potassium carbonate in the presence of catalytic amounts of tetra-n-butylammonium iodide (TBAI) in

  描述了一种在三氯化碳中使用三苯基膦对醇进行的核碱基和唑衍生物的一锅N-烷基化的简便有效方法。在这种方法中，在催化量的四正丁基碘化铵（TBAI）存在下，在回流的N，N-二甲基甲酰胺中，用三苯基膦，四氯化碳，核碱基或唑衍生物和碳酸钾的混合物处理醇，得到了相应的N-烷基衍生物，收率高。该方法学对于各种结构多样的伯醇是高效的，并且也可用于含有酸性NH键的其他N-杂环的N-烷基化。 碳环核苷-N-烷基化-核碱基-醇-三苯膦-四氯化碳-碳酸钾
• CEREBLON LIGANDS AND BIFUNCTIONAL COMPOUNDS COMPRISING THE SAME
  申请人：Arvinas, Inc.

  公开号：US20180215731A1

  公开（公告）日：2018-08-02

  The description relates to cereblon E3 ligase binding compounds, including bifunctional compounds comprising the same, which find utility as modulators of targeted ubiquitination, especially inhibitors of a variety of polypeptides and other proteins which are degraded and/or otherwise inhibited by bifunctional compounds according to the present disclosure. In particular, the description provides compounds, which contain on one end a ligand which binds to the cereblon E3 ubiquitin ligase and on the other end a moiety which binds a target protein such that the target protein is placed in proximity to the ubiquitin ligase to effect degradation (and inhibition) of that protein. Compounds can be synthesized that exhibit a broad range of pharmacological activities consistent with the degradation/inhibition of targeted polypeptides of nearly any type.

  该描述涉及cereblon E3连接酶结合化合物，包括包含相同成分的双功能化合物，这些化合物作为靶向泛素化的调节剂具有实用价值，尤其是抑制剂，可降解和/或以其他方式抑制根据本公开的双功能化合物。特别是，该描述提供了化合物，其一端含有与cereblon E3泛素连接酶结合的配体，另一端含有与目标蛋白结合的部分，使目标蛋白位于泛素连接酶附近以降解（和抑制）该蛋白。可以合成表现出广泛药理活性的化合物，与几乎所有类型的靶向多肽的降解/抑制一致。
• 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。
• One-pot synthesis of N-alkyl purine and pyrimidine derivatives from alcohols using TsIm: a rapid entry into carboacyclic nucleoside synthesis
  作者：Mohammad Navid Soltani Rad、Ali Khalafi-Nezhad、Somayeh Behrouz、Mohammad Ali Faghihi、Abdolkarim Zare、Abolfath Parhami

  DOI：10.1016/j.tet.2007.11.101

  日期：2008.2

  A convenient and efficient one-pot N-alkylation of nucleobases from alcohols using N-(p-toluenesulfonyl)imidazole (TsIm) is described. In this method, treatment of alcohols with a mixture of purine or pyrimidine nucleobase, TsIm, K2CO3, and triethylamine in refluxing DMF regioselectively furnishes the corresponding N-alkyl nucleobases in good yields. This methodology is highly efficient for various structurally diverse primary alcohols. (C) 2007 Elsevier Ltd. All rights reserved.