2,4-bis(2-oxo-2-phenylethyl)-1,2,4-triazine-3,5(2H,4H)-dione | 1259224-43-5

• 英文名称: 2,4-bis(2-oxo-2-phenylethyl)-1,2,4-triazine-3,5(2H,4H)-dione
• CAS: 1259224-43-5
• 化学式: C₁₉H₁₅N₃O₄
• 分子量: 349.346
• InChiKey: XKDGRJFYZAMOCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.17
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  91.03
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2,4-bis(2-oxo-2-phenylethyl)-1,2,4-triazine-3,5(2H,4H)-dione 、 2-溴甲基丙烯酸乙酯 在 对苯二酚 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以78.5%的产率得到2,4-bis[(4-methylene-5-oxo-2-phenyltetrahydrofuran-2-yl)methyl]-1,2,4-triazine-3,5(2H,4H)-dione
  参考文献：
  名称：

  Synthesis and antibacterial evaluation of 6-azapyrimidines with α-methylene-γ-(4-substituted phenyl)-γ-butyrolactone pharmacophores

  摘要：

  A series of 6-substituted 2-[(4-methylene-5-oxo-2-(4-substituted phenyl) tetrahydrofuran-2-yl)methyl]-1,2,4-triazine-3,5(2H,4H)-diones (5, 6) and 2,4-bis[(4-methylene-5-oxo-2-(4-substituted phenyl) tetrahydrofuran-2-yl)methyl]-1,2,4-triazine-3,5(2H,4H)-diones (9, 10) were designed, synthesized, and evaluated for antibacterial activity against Gram-positive and Gram-negative microorganisms. The synthesis of these compounds involved the Reformatsky-type reaction between ethyl alpha-(bromomethyl)acrylate and the proper ketones. Among these compounds, 2-[(4-methylene-5-oxo-2-phenyl tetrahydrofuran-2-yl)methyl]-1,2,4-triazine-3,5(2H,4H)-dione (5a) is the most active compound and shown the selective inhibition activity against Proteus vulgaris.

  DOI：

  10.1007/s00044-010-9438-7
• 作为产物：
  描述：

  6-氮杂脲嘧啶 、 2-溴苯乙酮 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以82.9%的产率得到2,4-bis(2-oxo-2-phenylethyl)-1,2,4-triazine-3,5(2H,4H)-dione
  参考文献：
  名称：

  Synthesis and antibacterial evaluation of 6-azapyrimidines with α-methylene-γ-(4-substituted phenyl)-γ-butyrolactone pharmacophores

  摘要：

  A series of 6-substituted 2-[(4-methylene-5-oxo-2-(4-substituted phenyl) tetrahydrofuran-2-yl)methyl]-1,2,4-triazine-3,5(2H,4H)-diones (5, 6) and 2,4-bis[(4-methylene-5-oxo-2-(4-substituted phenyl) tetrahydrofuran-2-yl)methyl]-1,2,4-triazine-3,5(2H,4H)-diones (9, 10) were designed, synthesized, and evaluated for antibacterial activity against Gram-positive and Gram-negative microorganisms. The synthesis of these compounds involved the Reformatsky-type reaction between ethyl alpha-(bromomethyl)acrylate and the proper ketones. Among these compounds, 2-[(4-methylene-5-oxo-2-phenyl tetrahydrofuran-2-yl)methyl]-1,2,4-triazine-3,5(2H,4H)-dione (5a) is the most active compound and shown the selective inhibition activity against Proteus vulgaris.

  DOI：

  10.1007/s00044-010-9438-7

文献信息

• Visible-Light-Induced Oxyalkylation of 1,2,4-Triazine-3,5(2<i>H</i>, 4<i>H</i>)-diones with Ethers <i>via</i> Oxidative Cross-Dehydrogenative Coupling
  作者：Yushi Tan、Wu Xuekun、Ya-Ping Han、Yuecheng Zhang、Hong-Yu Zhang、Jiquan Zhao

  DOI：10.1021/acs.joc.2c00669

  日期：2022.7.1

  An efficient and convenient method to synthesize 6-oxyalkylated 1,2,4-triazine-3,5(2H, 4H)-diones has been developed via visible-light-induced cross-dehydrogenative coupling reaction between 1,2,4-triazine-3,5(2H, 4H)-diones and ethers with a wide range of functional group tolerance. The present transformation employs the cheap and low-toxic 2-tert-butylanthraquinone as a metal-free photocatalyst and

  1,2,4-3,5 (2 H , 4 H )-二酮类化合物通过可见光诱导的1,2,4之间的交叉脱氢偶联反应合成6-氧烷基化1,2,4-三嗪-3,5(2 H , 4 H )-二酮类化合物-triazine-3,5(2 H , 4 H )-二酮和醚，具有广泛的官能团耐受性。本次改造采用廉价低毒的二叔-丁基蒽醌在室温下作为无金属光催化剂和空气作为绿色氧化剂。此外，这种反应也可以由作为清洁能源的阳光驱动。该方法的合成效用通过克级反应和在生物活性分子关键中间体制备中的应用得到进一步证明。
• Multicomponent Radical Cross‐Coupling Reaction of [1.1.1]Propellane: Synthesis of 1‐Arylthiol‐3‐Heteroaryl Bicyclo[1.1.1]pentanes †
  作者：Lin Li、Yumiao Liu、Jian Li、Qing Chen、Pengfei Zhang、Jiabin Shen、Jirong Wu

  DOI：10.1002/adsc.202300534

  日期：2023.9.19

  reaction of [1.1.1]propellane with N-heterocycles and disulfides is described. The mild conditions enabled the installation of the BCP motif in a wide variety of compounds in the absence of photocatalyst, additive and metal catalyst, with excellent functional group tolerance, This methodology opens a approach for the synthesis of potentially bioactive 1-arylthiol-3-heteroaryl bicyclo[1.1.1]pentanes in

  本文描述了[1.1.1]丙烷与N-杂环和二硫化物的可见光介导的多组分自由基交叉偶联反应。温和的条件使得BCP基序能够在没有光催化剂、添加剂和金属催化剂的情况下安装在多种化合物中，并且具有优异的官能团耐受性，该方法为合成具有潜在生物活性的1-芳硫醇-3-开辟了一条途径。杂芳基双环[1.1.1]戊烷的产率中等至良好。
• Synthesis of 1-(Halo)alkyl-3-heteroaryl Bicyclo[1.1.1]pentanes Enabled by a Photocatalytic Minisci-type Multicomponent Reaction
  作者：Jiashun Zhu、Yu Hong、Yuxin Wang、Yirui Guo、Yuru Zhang、Zhigang Ni、Wanmei Li、Jun Xu

  DOI：10.1021/acscatal.4c00740

  日期：2024.4.19

  it urgent to develop a more simple and practical protocol. To confront the limitations and enrich Minisci-type chemistry, herein, we disclose a photocatalytic Minisci-type multicomponent reaction for the synthesis of various (halo)alkyl BCP-aryls using [1.1.1]propellane, alkyl halides, and unfunctionalized heteroarenes as starting materials. Diverse kinds of unfunctionalized heteroarenes and alkyl

  芳基取代的双环[1.1.1]戊烷（BCP-芳基）衍生物代表了联芳支架最重要的生物等排体，广泛存在于众多复杂的药物分子中。目前仅使用叔自由基前体、预官能化杂芳烃、有毒过渡金属和昂贵光催化剂的合成方法的局限性使得迫切需要开发更简单实用的方案。为了应对局限性并丰富Minisci型化学，本文中，我们公开了一种光催化Minisci型多组分反应，用于使用[1.1.1]丙烷、烷基卤和未官能化杂芳烃作为起始物合成各种（卤代）烷基BCP-芳基。材料。衍生自各种烷基氯、烷基溴和氟烷基碘的多种未官能化杂芳烃和烷基（伯碳、仲碳和叔碳）在该转化中非常相容。产品衍生化和药学相关分子的后期功能化进一步增强了该方法的实用性。机理研究表明，由连续光致电子转移（ConPET）过程引发的激进中继机制正在运行。我们预计该方法将作为合成（卤）烷基 BCP-芳基作为联芳基型药物衍生物的生物电子等排体的有用工具，最终在药物发现计划中产生巨大的实用性。
• Visible-Light-Induced C(sp²)–C(sp³) Cross-Dehydrogenative-Coupling Reaction of <i>N</i>-Heterocycles with <i>N</i>-Alkyl-<i>N</i>-methylanilines under Mild Conditions
  作者：Hong-Yu Zhang、Jianjun Chen、Cong-Cong Lu、Ya-Ping Han、Yuecheng Zhang、Jiquan Zhao

  DOI：10.1021/acs.joc.1c01207

  日期：2021.9.3