5-(3,4-dichlorobenzylidene)-1,3-dimethyl-2,4,6(1H,3H,5H)pyrimidinetrione | 57280-35-0

• 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-(3,4-dichlorobenzylidene)-1,3-dimethyl-2,4,6(1H,3H,5H)pyrimidinetrione
• 英文别名: 5-(3,4-dichloro-benzylidene)-1,3-dimethyl-pyrimidine-2,4,6-trione；5-(3,4-dichlorobenzylidene)-1,3-dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione；5-[(3,4-dichlorophenyl)methylidene]-1,3-dimethyl-1,3-diazinane-2,4,6-trione
• CAS: 57280-35-0
• 化学式: C₁₃H₁₀Cl₂N₂O₃
• 分子量: 313.14
• InChiKey: OGERHQOUYIDUFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  57.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,4-二硫-2,5-二醇 、 5-(3,4-dichlorobenzylidene)-1,3-dimethyl-2,4,6(1H,3H,5H)pyrimidinetrione 以 水 为溶剂， 反应 0.5h， 生成 1-(3,4-dichlorophenyl)-4-hydroxy-7,9-dimethyl-2-thia-7,9-diazaspiro[4.5]decane-6,8,10-trione
  参考文献：
  名称：

  “On-water” catalyst-free, one-pot synthesis of quaternary centered and spiro-tetrahydrothiophene-barbiturate hybrids

  摘要：

  A green and efficient method have been developed for the synthesis of quaternary centered and spiro-barbiturate-tetrahydrothiophene hybrids via Knoevenagel condensation,1,4-thia-Michael and intramolecular Aldol reactions using "on water" concept under catalyst-free conditions. Systematic studies were carried out to find the role of the water and total reaction concentration (0.086 M) to promote the reaction in two steps (one-pot). The use of water as a reaction medium, catalyst-free conditions, broad substrate scope, one-pot approach for the creation of quaternary centered and spiro molecules are the advantages of this method. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2017.06.029
• 作为产物：
  描述：

  1,3-二甲基巴比妥酸 、 3,4-二氯苯甲醛 以 水 为溶剂， 反应 0.5h， 以83%的产率得到5-(3,4-dichlorobenzylidene)-1,3-dimethyl-2,4,6(1H,3H,5H)pyrimidinetrione
  参考文献：
  名称：

  Synthesis and DPPH Radical Scavenging Activity of 5-Arylidene-N,Ndimethylbarbiturates

  摘要：

  对24种N,N-二甲基巴比妥酸衍生物1-24进行了DPPH自由基清除活性筛选。这些化合物显示出优异的抗氧化活性。讨论了结构-活性关系，同时所有合成化合物均通过光谱技术和元素分析进行了表征。

  DOI：

  10.2174/157340611795564231

文献信息

• Phosphine-catalyzed [3 + 2] and [4 + 2] annulation reactions of ynones with barbiturate-derived alkenes
  作者：Xing Gao、Zhen Li、Wenjun Yang、Yang Liu、Wufeng Chen、Cheng Zhang、Lufei Zheng、Hongchao Guo

  DOI：10.1039/c7ob01034f

  日期：——

  The phosphine-catalyzed [3 + 2] annulation reaction of ynones and barbiturate-derived alkenes has been developed with the assistance of a weak acid, giving functionalized spirobarbiturate-cyclopentanones in moderate to excellent yields with excellent E/Z stereoselectivity. An unprecedented [4 + 2] annulation of ynones with barbiturate-derived alkenes was also achieved in the presence of a phosphine

  在弱酸的帮助下，膦类催化的炔酮和巴比妥酸酯衍生的烯烃的[3 + 2]环化反应得到了发展，使官能化的螺巴比妥酸酯-环戊烷酮的产率中等至优异，具有出色的E / Z立体选择性。在膦催化剂和无机碱的存在下，还实现了前所未有的[4 + 2]炔酮与巴比妥酸酯衍生的烯烃的环合反应，提供了生物学上令人感兴趣的1,5-二氢-2 H-吡喃[2,3- d ]嘧啶-2,4（3 H）-二酮衍生物。当使用双官能手性膦作为手性催化剂时，已经探索了[3 + 2]环化反应的不对称变体，并获得了中等的对映选择性。提出了一种合理的机制来阐明两种不同的反应途径。
• Chemoselective synthesis of 5,4′-imidazolinyl spirobarbiturates <i>via</i> NBS-promoted cyclization of unsaturated barbiturates and amidines
  作者：Hui Xu、Rong-Lu Huang、Zhu Shu、Ran Hong、Ze Zhang

  DOI：10.1039/d1ob00508a

  日期：——

  A selective cyclization of unsaturated barbiturates and amidines promoted by N-bromosuccinimide has been successfully developed to afford a vast variety of 5,4′-imidazolinyl spirobarbiturates in moderate to good yields. The present protocol features broad substrate scope, facile work-up procedure and mild reaction conditions, providing a novel strategy for the highly selective and efficient construction

  由N-溴代琥珀酰亚胺促进的不饱和巴比妥酸盐和脒的选择性环化已成功开发，以中等至良好的收率提供种类繁多的 5,4'-咪唑啉螺巴比妥酸盐。本协议具有广泛的底物范围、简便的后处理程序和温和的反应条件，为结构多样的螺咪唑啉的高选择性和高效构建提供了一种新策略。
• An Efficient Synthesis of New Dispiropyrrolidine Derivatives<i>via</i>Three-Component 1,3-Dipolar Cycloaddition Reaction
  作者：Yu Hu、Da-Qing Shi

  DOI：10.1002/jhet.1087

  日期：2013.2

  A series of new dispiropyrrolidine derivatives were synthesized via the three-component 1,3-dipolar cycloaddition reaction of azomethine ylides generated in situ by the decarboxylative condensation of acenaphthenequinone and sarcosine or l-thioproline with 5-benzylidene-1,3-dimethylpyrimidine-2,4,6-trione. The structures of the products were identified by IR, 1H-NMR, and HRMS spectra.

  通过三组分的脱羧缩合反应原位生成的偶氮甲的三组分1,3-双极环加成反应合成了一系列新的双螺吡咯烷衍生物。ac苯醌和肌氨酸或l-硫代脯氨酸与5-亚苄基-1,3-二甲基嘧啶-2,4,6-三酮。产物的结构通过IR，1 H-NMR和HRMS光谱鉴定。
• An Efficient Synthesis of Novel Dispirooxindole Derivatives via One-Pot Three-Component 1,3-Dipolar Cycloaddition Reactions
  作者：Zhibin Huang、Qian Zhao、Gang Chen、Huiyuan Wang、Wei Lin、Lexing Xu、Hongtao Liu、Juxian Wang、Daqing Shi、Yucheng Wang

  DOI：10.3390/molecules171112704

  日期：——

  A series of novel dispirooxindoles have been synthesized through three-component 1,3-dipolar cycloaddition of azomethine ylides generated in situ by the decarboxylative condensation of isatin and an α-amino acid with the dipolarophile 5-benzylidene-1,3-dimethylpyrimidine-2,4,6-trione. This method has the advantages of mild reaction conditions, high atom economy, excellent yields, and high regio- and

  通过靛红和α-氨基酸与偶极亲和物5-苄叉-1,3-二甲基嘧啶-2的脱羧缩合原位生成的偶氮甲碱叶立德的三组分1,3-偶极环加成反应合成了一系列新型二螺环吲哚,4,6-三酮。该方法具有反应条件温和、原子经济性高、产率高、区域选择性和立体选择性高等优点。
• Aerobic CuBr₂-Catalyzed Oxidative Coupling Reaction of Amidines with Exocyclic α,β-Unsaturated Cycloketones for the Synthesis of Spiroimidazolines
  作者：Fei-Hong Huang、Ming-Jun Li、Zeng-Yang He、Qi-Yue Zhu、Ze-Ming Huang、Qing-Hai Li、Hui Xu、Ze Zhang

  DOI：10.1021/acs.joc.3c00016

  日期：2023.6.2

  A CuBr2-catalyzed cascade reaction of amidines with exocyclic α,β-unsaturated cycloketones was developed, affording a large variety of spiroimidazolines in moderate to excellent yields. The reaction process involved the Michael addition and copper(II)-catalyzed aerobic oxidative coupling, in which O2 from air acted as the oxidant and H2O was the sole byproduct.

  开发了CuBr 2催化的脒与环外 α,β-不饱和环酮的级联反应，以中等至优异的收率提供了多种螺咪唑啉。反应过程涉及迈克尔加成和铜(II) 催化的有氧氧化偶联，其中空气中的O 2作为氧化剂，H 2 O是唯一的副产物。