dimethyl 1,3-bis(4-chlorophenyl)-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylate | 1229593-45-6

• 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-bis(4-chlorophenyl)-1,2,3,6-tetrahydropyrimidine-4,5-dicarboxylate
• 英文别名: Dimethyl 1,3-bis(4-chlorophenyl)-2,4-dihydropyrimidine-5,6-dicarboxylate
• CAS: 1229593-45-6
• 化学式: C₂₀H₁₈Cl₂N₂O₄
• 分子量: 421.28
• InChiKey: CVJKYAHEPOOFMI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 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：

  聚合甲醛 、 对氯苯胺 、 丁炔二酸二甲酯 在 molybdenum(VI) oxide 作用下， 以 水 为溶剂， 反应 0.13h， 以90%的产率得到dimethyl 1,3-bis(4-chlorophenyl)-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

• 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。
• Reaction of dialkyl 2-butynoate with aniline and formaldehyde: revision of the structure of the product
  作者：A. Srikrishna、M. Sridharan、K.R. Prasad

  DOI：10.1016/j.tet.2010.03.084

  日期：2010.5

  Dimethyl 3-(aryl)-3,6-dihydro-2H-1,3-oxazine-4,5-dicarboxylate structure assigned for the products obtained in the Bronsted acid catalyzed reaction of dimethyl but-2-ynoates with anilines and an excess of formaldehyde in methanol has been revised to methyl 1-(aryl)-3-(methoxymethyl)-4,5-dioxopyrrolidine-3-carboxylate.

  3-（芳基）-3,6-二氢-2 H -1,3-恶嗪-4,5-二羧酸二甲酯结构被指定用于布朗斯台德酸催化的丁-2-酸二甲酯与苯胺和苯胺的反应中获得的产物甲醇中过量的甲醛已修改为1-（芳基）-3-（甲氧基甲基）-4,5-二氧杂吡咯烷-3-羧酸甲酯。
• Green synthesis of tetrahydropyrimidine analogues and evaluation of their antimicrobial activity
  作者：Sunil N. Darandale、Dattatraya N. Pansare、Nayeem A. Mulla、Devanand B. Shinde

  DOI：10.1016/j.bmcl.2013.02.099

  日期：2013.5

  It is the first report of 1,3,4,5-tetrasubstituted 1,2,3,6-tetrahydropyrimidines derivatives, catalyzed by ZrOCl2. The mild reaction conditions, excellent yields in shorter reaction time and evasion of cumbersome workup procedures make this process economically lucrative for industrial application. The novelty and highlight of the present method is the promising antibacterial and antifungal activity shown by compounds (4a, 4b, 4e, 4f, 4h and 4l) compared to standard. (C) 2013 Elsevier Ltd. All rights reserved.