5,5'-Bis-(1,3-dimethyl-uracil) | 7033-42-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 5,5'-Bis-(1,3-dimethyl-uracil)
• 英文别名: 5,5'-Biuracil, 1,1',3,3'-tetramethyl-；5-(1,3-dimethyl-2,4-dioxopyrimidin-5-yl)-1,3-dimethylpyrimidine-2,4-dione
• CAS: 7033-42-3
• 化学式: C₁₂H₁₄N₄O₄
• 分子量: 278.268
• InChiKey: QFNYLIFBGQVEOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  81.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,3-二甲基脲嘧啶 在 sodium tetrachloroaurate(III) 作用下， 以 水 为溶剂， 反应 72.0h， 以22%的产率得到5,5'-Bis-(1,3-dimethyl-uracil)
  参考文献：
  名称：

  5,5′-Diuracilyl Species from Uracil and [AuCl4]−: Nucleobase Dimerization Brought about by a Metal

  摘要：

  DOI：

  10.1002/(sici)1521-3773(19990802)38:15<2274::aid-anie2274>3.0.co;2-j

文献信息

• Oxidative Cleavage of a Cyclobutane Pyrimidine Dimer by Photochemically Generated Nitrate Radicals (NO₃^•)
  作者：Oliver Krüger、Uta Wille

  DOI：10.1021/ol0157252

  日期：2001.5.1

  [reaction: see text] Photochemically generated nitrate radicals (NO(3)(*)) cleave the stereoisomeric N,N-dimethyl-substituted uracil cyclobutane dimers 1a-d into the monomeric uracil derivative 2 as the major reaction pathway. A preferred splitting of the syn dimers 1a,b was observed. The reaction is expected to proceed through initial one-electron oxidation with formation of an intermediate cyclobutane

  [反应：请参见文本]光化学生成的硝酸根（NO（3）（*））将立体异构体N，N-二甲基取代的尿嘧啶环丁烷二聚体1a-d裂解为单体尿嘧啶衍生物2作为主要反应途径。观察到顺式二聚体1a，b的优选分裂。预计该反应将通过最初的单电子氧化进行反应，并形成一个中间环丁烷自由基阳离子11。除了环还原反应外，还建议使用11竞争的反应步骤，从而导致观察到的副产物。
• Photoinduced cross-coupling reaction of 5-bromo-1,3-dimethyluracil to electron-rich aromatics
  作者：Satoru Ito、Isao Saito、Teruo Matsuura

  DOI：10.1016/s0040-4020(01)97713-0

  日期：——

  that the singlet excited states of the naphthalenes are involved in the unsensitized coupling reaction. The kqτ values of the fluorescence quenching of 1,4-dimethoxynaphthalene 2 and 1-methoxynaphthalene 4 by 1 in acetonitrile were comparable with those obtained from the kinetics of the coupling reactions. On the basis of this fact and the fluorescence-quenching rate constants kq in acetonitrile ranging

  在用耐热玻璃过滤的光照射下，将5-溴-1,3-二甲基尿嘧啶1与甲基和甲氧基萘2-7偶联，得到5-萘-1,3-二甲基尿嘧啶8-13。除了2，3-二甲氧基萘3和2-甲氧基萘5的情况外，通过三重态敏化没有形成偶联产物。表明萘的单线激发态与未敏化的偶联反应有关。第k q τ1,4-二甲氧基萘的荧光淬灭的值2和1-甲氧基萘4由1乙腈中的丁腈与通过偶联反应动力学获得的丁腈可比。基于这一事实，乙腈中的荧光猝灭速率常数k q在10 8至10 9 M -1 sec -1之间，因此提出了可能通过单线态激基复合物参与电子转移过程的交叉耦合反应。
• Palladium(II)-catalyzed oxidative homo-coupling of 1,3-dimethyluracil derivatives
  作者：Ko Hoon Kim、Hyun Seung Lee、Sung Hwan Kim、Jae Nyoung Kim

  DOI：10.1016/j.tetlet.2011.12.135

  日期：2012.3

  A palladium-catalyzed oxidative homo-coupling of 1,3-dimethyluracil was examined. Two types of uracil dimer, C5–C5′ linked dimer and C5–C6′ linked dimer were obtained in variable yields depending on the conditions along with a low yield of C5–C5′ and C6–C5′ linked uracil trimer.

  检查了钯催化的1，3-二甲基尿嘧啶的氧化均偶联。根据条件的不同，可得到两种类型的尿嘧啶二聚体：C5-C5'连接的二聚体和C5-C6'连接的二聚体，以及C5-C5'和C6-C5'连接的尿嘧啶三聚体的产量低。
• Palladium-catalyzed benzoin-mediated redox process leading to biaryls from aryl halides
  作者：Bo Ram Park、Ko Hoon Kim、Taek Hyeon Kim、Jae Nyoung Kim

  DOI：10.1016/j.tetlet.2011.06.045

  日期：2011.8

  An expedient synthetic procedure of biaryl derivatives was developed using a palladium-catalyzed, benzoin-mediated redox process from aryl halides. Various biaryls were synthesized in good yields in short time. (C) 2011 Elsevier Ltd. All rights reserved.
• C-H Trifluoromethylations of 1,3-Dimethyluracil and Reactivity of the Products in C-H Arylations
  作者：Michal Hocek、Miroslava Ćerňová、Radek Pohl、Blanka Klepetářová

  DOI：10.3987/com-14-12958

  日期：——

  Diverse electrophilic, nucleophilic and radical C-H trifluoromethylations of 1,3-dimethyluracil were systematically studied in order to prepare either 5- or 6-(trifluoromethyl)uracil derivatives. Electrophilic reagents led only to dimeric bis-uracil products, whereas the radical trifluoromethylation by CF3SO2Na in presence of t-BuOOH gave 1,3-dimethyl-5-(trifluoromethyl)uracil (2) in good yield. The 6-(trifluoromethyl)uracil derivative 3 was only prepared in low yield and in a mixture with 2 by Ir-catalyzed borylation followed by treatment with the Togni's reagent. Attempted Pd-catalyzed C-H arylations of 2 in the presence of Cs2CO3 gave mixtures of de-trifluoromethylated products, whereas the reaction with 4-iodotoluene in the presence of CsF gave the desired 6-aryl-5-trifluoromethyluracil derivative 8 in moderate yield and the reaction was not general for other aryl halides.