dimethyl 1,3-di-p-tolyl-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylate | 1253960-33-6

• 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: dimethyl 1,3-di-p-tolyl-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylate
• 英文别名: dimethyl 1,2,3,6-tetrahydro-1,3-bis(p-tolyl)pyrimidine-4,5-dicarboxylate；Dimethyl 1,3-bis(4-methylphenyl)-2,4-dihydropyrimidine-5,6-dicarboxylate；dimethyl 1,3-bis(4-methylphenyl)-2,4-dihydropyrimidine-5,6-dicarboxylate
• CAS: 1253960-33-6
• 化学式: C₂₂H₂₄N₂O₄
• 分子量: 380.444
• InChiKey: IWCPEECIGDXUDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  聚合甲醛 、 乙烷,三氯氟- 、 丁炔二酸二甲酯 在 molybdenum(VI) oxide 作用下， 以 水 为溶剂， 反应 0.08h， 以95%的产率得到dimethyl 1,3-di-p-tolyl-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylate
  参考文献：
  名称：

  Nano-MoO 3作为一种高效多相催化剂，用于在水中一锅法合成四氢嘧啶衍生物

  摘要：

  一种绿色高效的一锅法合成 16 种 1,3,4,5-四取代的 1,2,3,6-四氢嘧啶，其中四种是新的，使用涉及苯胺、甲醛和二烷基的三组分反应已经实现了在室温下由纳米 MoO3 催化在水性介质中制备乙炔二羧酸酯。

  DOI：

  10.3184/174751914x14115772243815

文献信息

• Nano-MoO₃ as a Highly Efficient Heterogeneous Catalyst for a One-Pot Synthesis of Tetrahydropyrimidine Derivatives in Water
  作者：Elham Zarenezhad、Mohammad Navid Soltani Rad、Mohammad Hossein Mosslemin、Masoumeh Tabatabaee、Somayeh Behrouz

  DOI：10.3184/174751914x14115772243815

  日期：2014.10

  A green and highly efficient one-pot synthesis of 16 1,3,4,5-tetrasubstituted 1,2,3,6-tetrahydropyrimidines, four of which are new, using a three-component reaction involving an aniline, formaldehyde and a dialkyl acetylenedicarboxylate in aqueous media at room temperature catalysed by nano-MoO3 has been achieved.

  一种绿色高效的一锅法合成 16 种 1,3,4,5-四取代的 1,2,3,6-四氢嘧啶，其中四种是新的，使用涉及苯胺、甲醛和二烷基的三组分反应已经实现了在室温下由纳米 MoO3 催化在水性介质中制备乙炔二羧酸酯。
• An Efficient Multicomponent Synthesis of Polysubstituted Pyrrolidines and Tetrahydropyrimidines Starting Directly from Nitro Compounds in Water¹
  作者：Biswanath Das、Digambar Shinde、Boddu Kanth、Gandham Satyalakshmi

  DOI：10.1055/s-0030-1258138

  日期：2010.8

  A distinct approach for the synthesis of 1,3,3-trisubstituted 4,5-dioxopyrrolidines and 1,3,4,5-tetrasubstituted 1,2,3,6-tetrahydropyrimidines has been discovered, in the form of a three-component reaction of nitroarenes, formaldehyde, and dialkyl acetylenedicarboxylates using indium in dilute aqueous HCl at room temperature. The molar ratios of these substrates are 1:1:4 and 2:1:4 for the preparation of dioxopyrrolidines and tetrahydropyrimidines, respectively. The reactions involve the reduction of nitro compounds to amines, which are simultaneously attacked by dialkyl acetylenedicarboxylates and formaldehyde. The products are formed in good to high yields.

  发现了一种合成1,3,3-三取代4,5-二氧吡咯烷和1,3,4,5-四取代1,2,3,6-四氢嘧啶的新方法，采用亚硝基芳烃、甲醛和二烷基乙炔二羧酸酯的三组分反应，使用稀盐酸中的铟在室温下进行。这些底物的摩尔比为1:1:4和2:1:4，分别用于合成二氧吡咯烷和四氢嘧啶。反应过程中，亚硝基化合物被还原为胺，同时被二烷基乙炔二羧酸酯和甲醛攻击。生成的产物收率良好到很高。
• Efficient Synthesis of Tetrahydropyrimidines and Pyrrolidines by a Multicomponent Reaction of Dialkyl Acetylenedicarboxylates (=Dialkyl But-2-ynedioates), Amines, and Formaldehyde in the Presence of Iodine as a Catalyst
  作者：Biswanath Das、Boddu Shashi Kanth、Digambar Balaji Shinde、Vinod T. Kamble

  DOI：10.1002/hlca.201100185

  日期：2011.11

  Iodine was explored as an efficient catalyst for the synthesis of tetrahydropyrimidines 4 and pyrrolidines 5 by a multicomponent reaction of dialkyl acetylenedicarboxylates (=dialkyl but‐2‐ynedioates) 1, amines 2, and HCHO 3 at room temperature (Scheme). When the molar ratios of these substrates were 1 : 2 : 4 and 1 : 1 : 4, tetrahydropyrimidines and pyrrolidines were formed, respectively. The products

  碘进行了探讨作为四氢嘧啶的合成的有效催化剂4和吡咯烷5通过二烷基acetylenedicarboxylates（=二烷基丁-2- ynedioates）的多组分反应1，胺2，和HCHO 3在室温（方案）。当这些底物的摩尔比为1：2：4和1：1：4时，分别形成四氢嘧啶和吡咯烷。在短时间内（25-35分钟）以高收率（73-85％）获得了产品。
• Molecular Iodine–Catalyzed Synthesis of 1,2,3,6-Tetrahydropyrimidines
  作者：Lingaiah Nagarapu、Hanmanth Reddy Vulupala、Ch. Venkatanarsimhaji、Rajashaker Bantu、A. Ramakrishna Reddy

  DOI：10.1080/00397911.2011.554061

  日期：2012.7.15

  A short and simple synthesis of tetrahydropyrimidine derivatives were accomplished in good to excellect yields at room temperature by the reaction of dimethylacetalynedicarboxylate, aniline, and formaldehyde in the presence of 5 mol% of molecular iodine at room temperature in ethanol for 5 min.
• 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