methyl 1,2,3,4-tetrahydro-4-(4-methoxyphenyl)-1,3,6-trimethyl-2-oxopyrimidine-5-carboxylate | 1103466-98-3

• 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: methyl 1,2,3,4-tetrahydro-4-(4-methoxyphenyl)-1,3,6-trimethyl-2-oxopyrimidine-5-carboxylate
• 英文别名: 1,3,6-trimethyl-4-(4-methoxyphenyl)-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid methyl ester；4-(4-methoxy-phenyl)-1,3,6-trimethyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid methyl ester；methyl 4-(4-methoxyphenyl)-1,3,6-trimethyl-2-oxo-4H-pyrimidine-5-carboxylate
• CAS: 1103466-98-3
• 化学式: C₁₆H₂₀N₂O₄
• 分子量: 304.346
• InChiKey: OCMXCWOBDZGUCN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,3-二甲基脲 、 4-甲氧基苯甲醛 、 乙酰乙酸甲酯 在 ammonium cerium (IV) nitrate 作用下， 以 neat (no solvent) 为溶剂， 反应 0.03h， 以92%的产率得到methyl 1,2,3,4-tetrahydro-4-(4-methoxyphenyl)-1,3,6-trimethyl-2-oxopyrimidine-5-carboxylate
  参考文献：
  名称：

  N，N'-二烷基-4-芳基-3,4-二氢嘧啶酮和亚硫醚：硝酸铈铈铵的催化合成及X射线晶体学测定的分子结构

  摘要：

  这项工作提出了在硝酸铈铵（CAN）存在下通过芳族醛，β-酮酸酯的直接缩合在微波辅助下无溶剂合成N，N'-二烷基-4-芳基-3,4-二氢嘧啶酮/硫酮的方法，以及N，N'-二烷基脲/硫脲。所采用方法的重点是：（i）反应物易于缩合为无任何副产物的产物；（ii）反应时间短，产率高，纯度高。所有合成的化合物都通过光谱技术（例如FTIR，1 H NMR，13 C NMR和Mass）进行了表征和建立。该化合物的结构通过单晶X射线衍射分析得到了进一步证实。

  DOI：

  10.1002/jhet.2735

文献信息

• The development of an ecofriendly procedure for alkaline metal (II) sulfate promoted synthesis of<i>N</i>,<i>N</i>′-dimethyl substituted (unsubstituted)-4-aryl-3,4-dihydropyrimidones (thiones) and corresponding bis-analogues in aqueous medium: Evaluation by green chemistry metrics
  作者：Chhanda Mukhopadhyay、Arup Datta

  DOI：10.1002/jhet.283

  日期：——

  Different alkaline metal (II) sulfates were used as catalysts for the N,N′-dimethyl substituted as well as unsubstituted 4-aryl-3,4-dihydropyrimidones (thiones) and their corresponding bis-analogues in aqueous medium. Among the various salts, MgSO4·7H2O (Epsom salt) proved to be the best catalyst giving the desired products in good to excellent yields. This catalyst enables the construction of a series

  在水性介质中，将不同的碱金属（II）硫酸盐用作N，N'-二甲基取代的和未取代的4-芳基-3,4-二氢嘧啶酮（硫酮）及其相应的双类似物的催化剂。在各种盐中，MgSO 4 ·7H 2 O（泻盐）被证明是最好的催化剂，以良好至极佳的收率提供了所需的产物。该催化剂能够构建一系列化合物库，特别是对于N，N'-二甲基取代的DHPM，其合成在文献中非常罕见。通过绿色化学的应用评估了在多种底物上的反应指标和非常好的相关性。J.杂环化​​学.2010。
• Pharmacologically Relevant Bifunctional Compounds Containing Chloroquinoline and Dihydropyrimidone Moieties: Syntheses and Crystal Structures of a Target Molecule and Selected Intermediates
  作者：Nicholas D. Watermeyer、Kelly Chibale、Mino R. Caira

  DOI：10.1007/s10870-009-9568-2

  日期：2009.10

  We report the regioselective synthesis and X-ray structure of the pharmacologically relevant 3-[2-(7-chloro-quinolin-4-ylamino)-ethylcarbamoyl]-4-(4-methoxy-phenyl)-1,6-dimethyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid methyl ester (3) (triclinic, space group $$ P\bar1} $$ , a = 11.1775 (3), b = 13.6470 (4), c = 16.3680 (6) Å, α = 82.645 (1), β = 86.423 (1), γ = 88.415 (2)°, V = 2470.9 (1) Å3, Z = 4). Further support for the regioselectivity is provided by the X-ray structures of two intermediates, namely 4-(4-methoxy-phenyl)-1,6-dimethyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid methyl ester, 8 (monoclinic, space group P21/c, a = 11.7710 (2), b = 5.5290 (1), c = 22.9500 (5) Å, β = 104.342 (1)°, V = 1447.08 (5) Å3, Z = 4), and 4-(4-methoxy-phenyl)-1,3,6-trimethyl-2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylic acid methyl ester, 9 (monoclinic, space group P21/c, a = 16.6529 (7), b = 10.9426 (4), c = 8.2819 (3) Å, β = 91.395 (2)°, V = 1508.7 (1) Å3, Z = 4), which are also reported. The three compounds display significant differences in the conformations of their DHPM rings as well as a variety of hydrogen bonding arrangements in their crystals. The synthetic strategy for deriving pharmacologically-relevant bifunctional compounds based on linked dihydropyrimidone and chloroquinoline moieties is reported, together with supporting X-ray structures of two synthetic intermediates and a representative target compound.

  我们报道了药理学相关的3-[2-(7-氯-喹啉-4-基氨基)-乙基氨基甲酰基]-4-(4-甲氧基-苯基)-1,6-二甲基-的区域选择性合成和X射线结构。 2-氧代-1,2,3,4-四氢-嘧啶-5-甲酸甲酯 (3)（三斜晶系，空间群 $$ P\bar1} $$ , a = 11.1775 (3), b = 13.6470 (4)、c = 16.3680 (6) Å、α = 82.645 (1)、β = 86.423 (1)、γ = 88.415 (2)°、V = 2470.9 (1) Å3、Z = 4)。两种中间体的X射线结构进一步支持了区域选择性，即4-(4-甲氧基-苯基)-1,6-二甲基-2-氧代-1,2,3,4-四氢-嘧啶- 5-羧酸甲酯，8（单斜晶系，空间群 P21/c，a = 11.7710 (2)，b = 5.5290 (1)，c = 22.9500 (5) Å，β = 104.342 (1)°，V = 1447.08 (5) Å3, Z = 4), 和 4-(4-甲氧基-苯基)-1,3,6-三甲基-2-氧代-1,2,3,4-四氢-嘧啶-5-甲酸甲基酯，9（单斜晶系，空间群 P21/c，a = 16.6529 (7)，b = 10.9426 (4)，c = 8.2819 (3​​) Å，β = 91.395 (2)°，V = 1508.7 (1) Å3， Z = 4），这也被报告。这三种化合物在 DHPM 环的构象以及晶体中的各种氢键排列方面表现出显着差异。报道了基于连接的二氢嘧啶酮和氯喹啉部分衍生药理学相关双功能化合物的合成策略，以及两种合成中间体和代表性目标化合物的支持X射线结构。
• <i>N,N′</i>-Dialkyl-4-Aryl-3,4-Dihydropyrimidinones and Thiones: Ceric Ammonium Nitrate Catalyzed Synthesis and Molecular Structure Determination by X-ray Crystallography
  作者：Chingrishon Kathing、Sushil Kumar、Shokip Tumtin、Nongthombam Geetmani Singh、Jims World Star Rani、Ridaphun Nongrum、Rishanlang Nongkhlaw

  DOI：10.1002/jhet.2735

  日期：2017.3

  This work presents a microwave assisted solvent‐free synthesis of N,N′‐dialkyl‐4‐aryl‐3,4‐dihydropyrimidinones/thiones in the presence of Ceric Ammonium Nitrate (CAN) via direct condensation of aromatic aldehydes, β‐keto ester, and N,N′‐dialkylurea/thiourea. The highlights of the methodology adopted are (i) facile condensation of the reactants into product without any side‐products, and (ii) short

  这项工作提出了在硝酸铈铵（CAN）存在下通过芳族醛，β-酮酸酯的直接缩合在微波辅助下无溶剂合成N，N'-二烷基-4-芳基-3,4-二氢嘧啶酮/硫酮的方法，以及N，N'-二烷基脲/硫脲。所采用方法的重点是：（i）反应物易于缩合为无任何副产物的产物；（ii）反应时间短，产率高，纯度高。所有合成的化合物都通过光谱技术（例如FTIR，1 H NMR，13 C NMR和Mass）进行了表征和建立。该化合物的结构通过单晶X射线衍射分析得到了进一步证实。