diethyl 1,3-dibenzyl-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: diethyl 1,3-dibenzyl-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylate
• 英文别名: Diethyl-1,3-dibenzyl-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylate；diethyl 1,3-dibenzyl-2,4-dihydropyrimidine-5,6-dicarboxylate
• 化学式: C₂₄H₂₈N₂O₄
• 分子量: 408.497
• InChiKey: DLAVUGMZTINFEP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl 1,3-dibenzyl-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylate 在 甲酸铵 、 palladium(II) hydroxide 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以93%的产率得到diethyl 1-benzyl-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylate
  参考文献：
  名称：

  1,3,5-三嗪烷与乙炔二甲酸二乙酯的正式 [2+2+2] 环加成反应：四氢嘧啶的方法

  摘要：

  在无金属条件下开发了一种前所未有的 1,3,5-三嗪烷与乙炔二羧酸二乙酯的 [2+2+2] 环加成反应，用于合成功能化的四氢嘧啶。已经进行了初步的机理研究以阐明反应过程。

  DOI：

  10.1002/ejoc.202101233
• 作为产物：
  描述：

  1,3,5-三苄基六氢-1,3,5-三嗪 、 丁炔二酸二乙酯 以 氯仿 为溶剂， 反应 60.0h， 以49%的产率得到diethyl 1,3-dibenzyl-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylate
  参考文献：
  名称：

  1,3,5-三嗪烷与乙炔二甲酸二乙酯的正式 [2+2+2] 环加成反应：四氢嘧啶的方法

  摘要：

  在无金属条件下开发了一种前所未有的 1,3,5-三嗪烷与乙炔二羧酸二乙酯的 [2+2+2] 环加成反应，用于合成功能化的四氢嘧啶。已经进行了初步的机理研究以阐明反应过程。

  DOI：

  10.1002/ejoc.202101233

文献信息

• Solvent-free one-pot synthesis of polysubstituted tetrahydropyrimidines and their antioxidant and antimicrobial properties
  作者：Shailaja Myadaraboina、Manjula Alla、Arunadevi Parlapalli、Sarangapani Manda

  DOI：10.1007/s11164-015-2063-9

  日期：2016.2

  Abstract A versatile and highly efficient one-pot multicomponent approach for the synthesis of novel multisubstituted tetrahydropyrimidine (dimethyl/diethyl-1,3-disubstituted-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylate) derivatives catalyzed by Bromo(dimethylsulfonium) bromide under solvent-free conditions has been developed. The protocol is eco-friendly, operationally simple, and proceeds in short

  摘要 一种通用且高效的一锅多组分方法，用于合成由溴（Bromo）催化的新型多取代四氢嘧啶（二甲基/二乙基-1,3-二取代-1,2,3,6-四氢嘧啶-4,5-二羧酸酯）衍生物。已经开发了无溶剂条件下的溴化二甲基s）溴化物。该方案环保，操作简单，反应时间短，可提供高产率，高纯度（90–95％）的稳定目标化合物，而无需任何副产物。此外，该方案的范围扩展到脂族底物，从而建立了催化剂的多功能性。筛选铅化合物的抗氧化剂和抗菌活性。其中，化合物 4a ， 4d ， 4e 与标准庆大霉素相比， 4j 具有优异的抗菌活性。与标准伊曲康唑相比，化合物 4e 和 4k 表现出优异的抗真菌活性。这项研究的结果表明，所有合成的化合物均以浓度依赖性方式清除了DPPH自由基。与标准抗坏血酸相比，该化合物的IC 50值为13.28至23.16 µM。发现化合物 4f 是良好的抗氧化剂。 图形概要 由一丁二酸，胺和甲醛经一
• Practical synthesis and mechanistic study of polysubstituted tetrahydropyrimidines with use of domino multicomponent reactions
  作者：Qiuhua Zhu、Huanfeng Jiang、Jinghao Li、Min Zhang、Xiujun Wang、Chaorong Qi

  DOI：10.1016/j.tet.2009.03.071

  日期：2009.6

  The practical synthesis of polysubstituted tetrahydropyrimidines 4 from but-2-ynedioates 1, amines 2, and formaldehyde 3 through a domino process of one-pot multicomponent reactions (MCRs) and the detailed mechanistic studies are described. The MCRs were performed under extremely mild reaction conditions and offered the desired products in excellent yields. The detailed studies on the mechanism of

  描述了通过一锅多组分反应（MCR）的多米诺法从丁-2-炔基1，胺2和甲醛3实际合成多取代的四氢嘧啶4的方法，以及详细的机理研究。MCR在极其温和的反应条件下进行，并以极高的收率提供了所需的产物。对MCRs机理的详细研究证明：（1）质子促进的多米诺序列由加氢胺化，氮杂-烯型反应，亲核加成和脱水环化组成；（2）溶剂可控制1和2：Z的加氢胺化立体选择性在与质子溶剂-异构体Ž / ë高达95：5和È -异构体与非质子溶剂Ê / Ž高达98：2，和ž异构体比更稳定ë -异构体; （3）Z-和E-烯胺中间体通过氮杂-烯型反应模型产生相同的所需产物。计算结果验证了MCR中的氮杂-烯型过程。
• Solvent-free synthesis of polyfunctional tetrahydropyrimidines promoted by recyclable ionic liquid
  作者：Mazaahir Kidwai、Neeraj Kumar Mishra、Saurav Bhardwaj

  DOI：10.1007/s13738-012-0202-4

  日期：2013.8

  The synthesis of nitrogen containing heterocyclic compounds from diethyl ester, formaldehyde, and various aromatic/aliphatic amines via a simple and efficient one-pot multicomponent reaction in ionic liquid is described. The catalyst can be recycled at least three times without obvious loss in catalytic activity.

  描述了在离子液体中通过简单高效的一锅多组分反应由二乙酯、甲醛和各种芳香族/脂肪族胺合成含氮杂环化合物。该催化剂可循环使用至少3次，催化活性没有明显损失。
• Gold catalyzed synthesis of tetrahydropyrimidines and octahydroquinazolines under ball milling conditions and evaluation of anticonvulsant potency
  作者：M. Vadivelu、A. A. Raheem、S. Sugirdha、G. Bhaskar、K. Karthikeyan、Chandrasekar Praveen

  DOI：10.24820/ark.5550190.p010.372

  日期：——

  A fast, mechanochemical and solvent-free synthesis of substituted tetrahydropyrimidines and octahydroquinazolines under Au(III)-catalysis has been developed. The practical feasibility, eco-friendliness and operational simplicity of this chemistry is exemplified by ball milling three components such as formaldehyde, amines and 2-butynedioates/dimedone in a shaker mill for as little as five minutes, thus avoiding the requirement of undesirable solvents and long reaction times. Moreover, this protocol furnishes the target compounds in high yields without any side products and in some cases offers products with excellent regioselectivity. Out of the 26 compounds screened for anticonvulsant potency, 11 compounds exhibited comparable activity against a standard drug.[GRAPHICS].
• Convenient One-Pot Synthesis of Multisubstituted Tetrahydropyrimidines via Catalyst-Free Multicomponent Reactions
  作者：Min Zhang、Huanfeng Jiang、Hailing Liu、Qiuhua Zhu

  DOI：10.1021/ol701592h

  日期：2007.10.1

  A novel and convenient one-pot synthesis of multisubstituted pyrimidine analogues via multicomponent reactions is disclosed. This catalyst-free domino reaction proceeded smoothly in good to excellent yields and offered several other advantages including short reaction time, a simple experimental workup procedure, and no toxic byproduct. In addition, the obtained products in our experiments are interesting nitrogen heterocyclic molecules containing alpha- and beta-amino acid blocks.