dimethyl 1,3-diphenyl-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylate | 1169473-81-7

• 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-diphenyl-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylate
• 英文别名: Dimethyl 1,3-diphenyl-2,4-dihydropyrimidine-5,6-dicarboxylate；dimethyl 1,3-diphenyl-2,4-dihydropyrimidine-5,6-dicarboxylate
• CAS: 1169473-81-7
• 化学式: C₂₀H₂₀N₂O₄
• 分子量: 352.39
• InChiKey: FOAAVDIOVZZVMO-UHFFFAOYSA-N

物化性质

• 沸点：
  493.4±45.0 °C(Predicted)
• 密度：
  1.252±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  丁炔二酸二甲酯 、 六氢-1,3,5-三苯基-1,3,5-三嗪 以 氯仿 为溶剂， 反应 60.0h， 以74%的产率得到dimethyl 1,3-diphenyl-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

• 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。
• 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。
• Silica-Supported Perchloric Acid (HClO₄-SiO₂): An Efficient Catalyst for One-Pot Synthesis of Functionalized Tetrahydropyrimidine Derivatives
  作者：Abu T. Khan、Md. Musawwer Khan、Deb Kumar Das、Mohan Lal

  DOI：10.1002/jhet.1017

  日期：2012.11

  HClO4–SiO2 has been found to be a highly efficient catalyst for the synthesis of substituted tetrahydropyrimidine and bis‐tertahydropyrimidine derivatives in good to excellent yields involving the reaction of dimethyl acetylenedicarboxylate, amines/diamines, and formaldehyde. One‐pot, atom economy, high‐bond forming efficiency, environmentally benign, good yields, and mild reaction conditions are some

  已发现HClO 4 -SiO 2是合成取代的四氢嘧啶和双-叔氢嘧啶衍生物的高效催化剂，其收率高至优异，涉及乙炔二羧酸二甲酯，胺/二胺和甲醛的反应。单锅，原子经济，高键形成效率，环境友好，高收率和温和的反应条件是这种多组分反应的显着特征。
• 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。