1-(2-溴乙基)-5-甲基嘧啶-2,4-二酮 | 53438-98-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 1-(2-溴乙基)-5-甲基嘧啶-2,4-二酮
• 英文名称: 1-(2-bromoethyl)thymine
• 英文别名: 1-(2-Bromoethyl)-5-methylpyrimidine-2,4(1H,3H)-dione；1-(2-bromoethyl)-5-methylpyrimidine-2,4-dione
• CAS: 53438-98-5
• 化学式: C₇H₉BrN₂O₂
• 分子量: 233.065
• InChiKey: MDPOWKDHWLSZEH-UHFFFAOYSA-N

物化性质

• 密度：
  1.568±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-溴乙基)-5-甲基嘧啶-2,4-二酮 在 氢氟酸 、 potassium tert-butylate 、 异氰酸苯酯 、 三乙胺 作用下， 以 四氢呋喃 、 乙腈 、 苯 为溶剂， 反应 123.0h， 生成 1-(3-Hydroxymethyl-4,5-dihydro-isoxazol-5-yl)-5-methyl-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Heterocyclic Nucleosede Analogues by Cycloaddition Reactions of 1-Vinylthymine with 1,3-Depoles

  摘要：

  1,3-Dipolar cycloaddition of 1-vinylthymine to azides, nitrile oxides, nitrones and nitronates has been investigated as a route to heterocyclic nucleoside analogues in which the nucleoside ribose moiety has been replaced by an alternative heterocycle. Reaction of 1-vinylthymine with highly reactive nitrile oxides affords 1(isoxazolin-5-yl)thymine products in excellent yield at room temperature. The less reactive nitrone dipoles undergo cycloaddition to 1-vinylthymine at elevated temperature to afford 1-(isoxazolidin-5-yl)thymine cycloadducts in good-to-moderate yields, but show a tendency to eliminate thymine from the cycloaddition products over long reaction times. Azide cycloadditions to 1-vinylthymine proceed only under forcing conditions to which the fragile triazoline products are unstable.

  DOI：

  10.1080/07328319808004220
• 作为产物：
  描述：

  胸腺嘧啶 在 sodium hydroxide 、 四溴化碳 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-(2-溴乙基)-5-甲基嘧啶-2,4-二酮
  参考文献：
  名称：

  在焦磷酸引起的胸腺嘧啶官能化的异硫脲受体的自组装中，模板辅助优先合成顺二聚体。

  摘要：

  [反应：见正文]研究了阴离子模板化对胸腺嘧啶官能化的异硫脲鎓受体的光二聚作用的影响。紫外线照射后，该受体在甲醇中的胸腺嘧啶部分形成一个光二聚体，而异硫脲鎓部分则通过两点氢键基序作为氧阴离子的结合位点。与游离受体的情况相比，焦磷酸盐（PPi）的存在导致优先形成同型光二聚体，这对于识别模板化的PPi是理想的。

  DOI：

  10.1021/ol0268485

文献信息

• NMR and UV Study of 1,1′-(<i>α</i>,<i>ω</i>-Alkanediyl)bis[thymine] and 1,1′-(<i>α</i>,<i>ω</i>-Alkanediyl)bis[uracil]
  作者：Toshio Itahara

  DOI：10.1246/bcsj.70.2239

  日期：1997.9

  Treatment of thymine or uracil with Br(CH2)nBr (n = 3—10) in the presence of t-BuOK gave 1,1′-(α,ω-alkanediyl)bis[thymine] or 1,1′-(α,ω-alkanediyl)bis[uracil] together with 1-(ω-bromoalkyl)thymine or 1-(ω-bromoalkyl)uracil. The structures of these products were determined on the basis of the coupling constants between 5- and 3-positions of uracil ring on the 1H NMR spectra. Molecular aggregation of the thymine and uracil rings of these compounds in aqueous solution was studied on the basis of their 1H NMR and UV spectra. A stacking interaction of the two thymine rings linked by shorter polymethylene chains such as trimethylene and tetramenthylene groups was observed.

  将胸腺嘧啶或尿嘧啶与Br(CH2)nBr（n = 3—10）在t-BuOK存在下处理，得到了1,1′-(α,ω-烷烃二基)双[胸腺嘧啶]或1,1′-(α,ω-烷烃二基)双[尿嘧啶]，以及1-(ω-溴烷基)胸腺嘧啶或1-(ω-溴烷基)尿嘧啶。这些产物的结构是基于尿嘧啶环中5位和3位之间的耦合常数在1H NMR光谱上的分析来确定的。基于它们的1H NMR和紫外光谱，研究了这些化合物在水溶液中胸腺嘧啶和尿嘧啶环的分子聚集情况。观察到由较短的聚亚 methylene 链（如三亚甲基和四亚甲基基团）连接的两个胸腺嘧啶环之间存在堆叠相互作用。
• Potential Supramolecular Cyclodextrin Dimers Using Nucleobase Pairs
  作者：Christophe Len、Florian Hamon、Bruno Violeau、Frédéric Turpin、Mathilde Bellot、Laurent Bouteiller、Florence Djedaini-Pilard

  DOI：10.1055/s-0029-1217988

  日期：2009.10

  The synthesis of six new cyclodextrin derivatives having nucleobase moiety is described. These two moieties are linked by different spacers, such as aminoethyl and 1,2,3-triazolyl groups. Example of association constants for complexation of adenine and thymine derivatives: K AT = 385 M-¹ using NMR methodology is reported. Study of interaction between four cyclodextrin derivatives and one adamantyl guest is described by ITC.

  描述了六种新型环糊精衍生物的合成，这些衍生物具有核苷碱基部分。这两部分通过不同的链间隔连接，例如氨乙基和1,2,3-三唑基团。报告了腺嘌呤和胸腺嘧啶衍生物的复合物结合常数示例：K AT = 385 M⁻¹，使用NMR方法进行测定。研究了四种环糊精衍生物与一种亚甲基客体之间的相互作用，使用微量热量法（ITC）进行了描述。
• Toward the Supramolecular Cyclodextrin Dimers Using Nucleobase Pairs
  作者：Christophe Len、Vanessa Legros、Florian Hamon、Bruno Violeau、Frédéric Turpin、Florence Djedaini-Pilard、Jérôme Désiré

  DOI：10.1055/s-0030-1258354

  日期：2011.1

  The synthesis of eleven new cyclodextrin derivatives having nucleobase moiety - thymin-1-yl, adenin-9-yl, and guanin-9-yl - is described. These two moieties are linked by different spacers, such as aminoethyl and 1,2,3-triazolyl group. Direct nucleophilic substitution and 1,3-dipolar cycloaddition were performed in good yields (13-73%) for some of the synthesized compounds.

  描述了十一种新型环糊精衍生物的合成，这些衍生物具有核苷碱基部分——胸腺嘧啶-1-基、腺嘌呤-9-基和鸟嘌呤-9-基。这两个部分通过不同的间隔体连接，例如氨基乙基和1,2,3-噁唑基。对于一些合成的化合物，直接亲核取代反应和1,3-偶极环加成反应均在良好的产率（13-73%）下完成。
• The Cohalogenation of 1-N-Vinylpyrimidinediones: A New Approach to Nucleoside Analogs
  作者：Nathalie Baret、Jean-Pierre Dulcere、Jean Rodriguez、Jean-Marc Pons、Robert Faure

  DOI：10.1002/(sici)1099-0690(200004)2000:8<1507::aid-ejoc1507>3.0.co;2-k

  日期：2000.4
• Synthesis and enzymatic evaluation of pyridinium-Substituted uracil derivatives as novel inhibitors of thymidine phosphorylase
  作者：Paul E Murray、Virginia A McNally、Stacey D Lockyer、Kaye J Williams、Ian J Stratford、Mohammed Jaffar、Sally Freeman

  DOI：10.1016/s0968-0896(01)00309-1

  日期：2002.3

  A series of water soluble N(1)- and C(6)-substituted uracil pyridinium compounds were prepared as potential inhibitors of thymidine phosphorylase (TP). The C(6)-uracil substituted derivatives were the most active. 1-[(5-Chloro-2,4-dihydroxy-pyrimidin-6-yl)methyl]pyridinium chloride, was identified as the best inhibitor being 5-fold more potent than the known inhibitor, 6-amino-5-bromouracil. (C) 2002 Elsevier Science Ltd. All rights reserved.