ethyl 4-(4-chlorophenyl)-6-methyl-2-oxo-1,2-dihydropyrimidine-5-carboxylate | 1091820-63-1

• 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: ethyl 4-(4-chlorophenyl)-6-methyl-2-oxo-1,2-dihydropyrimidine-5-carboxylate
• 英文别名: ethyl 6-methyl-4-(4-chlorophenyl)pyrimidin-2(1H)-one-5-carboxylate；ethyl 4-(4-chlorophenyl)-1,2-dihydro-6-methyl-2-oxopyrimidine-5-carboxylate；ethyl 4-(4-chlorophenyl)-6-methyl-2-oxo-1H-pyrimidine-5-carboxylate
• CAS: 1091820-63-1
• 化学式: C₁₄H₁₃ClN₂O₃
• 分子量: 292.722
• InChiKey: CZLIRPIWRZLKQN-UHFFFAOYSA-N

物化性质

• 熔点：
  181-183 °C
• 密度：
  1.33±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 4-(4-chlorophenyl)-6-methyl-2-oxo-1,2-dihydropyrimidine-5-carboxylate 在 三氯氧磷 作用下， 反应 0.75h， 生成 ethyl 2-chloro-4-(4-chlorophenyl)-6-methylpyrimidine-5-carboxylate
  参考文献：
  名称：

  Synthesis of 4-aminoquinoline–pyrimidine hybrids as potent antimalarials and their mode of action studies

  摘要：

  One of the most viable options to tackle the growing resistance to the antimalarial drugs such as artemisinin is to resort to synthetic drugs. The multi-target strategy involving the use of hybrid drugs has shown promise. In line with this, new hybrids of quinoline with pyrimidine have been synthesized and evaluated for their antiplasmodial activity against both CQ(S) and CQ(R) strains of Plasmodium falciparum. These depicted activity in nanomolar range and were found to bind to heme as well as AT rich pUC18 DNA. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.05.046
• 作为产物：
  描述：

  乙酰乙酸乙酯 在 硝酸 、 氯化铵 作用下， 反应 3.5h， 生成 ethyl 4-(4-chlorophenyl)-6-methyl-2-oxo-1,2-dihydropyrimidine-5-carboxylate
  参考文献：
  名称：

  Synthesis of 4-aminoquinoline–pyrimidine hybrids as potent antimalarials and their mode of action studies

  摘要：

  One of the most viable options to tackle the growing resistance to the antimalarial drugs such as artemisinin is to resort to synthetic drugs. The multi-target strategy involving the use of hybrid drugs has shown promise. In line with this, new hybrids of quinoline with pyrimidine have been synthesized and evaluated for their antiplasmodial activity against both CQ(S) and CQ(R) strains of Plasmodium falciparum. These depicted activity in nanomolar range and were found to bind to heme as well as AT rich pUC18 DNA. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.05.046

文献信息

• A novel combination of (diacetoxyiodo)benzene and tert-butylhydroperoxide for the facile oxidative dehydrogenation of 3,4-dihydropyrimidin-2(1H)-ones
  作者：Nandkishor N. Karade、Sumit V. Gampawar、Jeevan M. Kondre、Girdharilal B. Tiwari

  DOI：10.1016/j.tetlet.2008.09.045

  日期：2008.11

  A clean and efficient oxidative dehydrogenation of 3,4-dihydropyrimidin-2(1H)-ones to 1,2-dihydropyrimidines has been achieved through a novel combination of (diacetoxyiodo)benzene and tert-butylhydroperoxide in CH2Cl2.

  通过在CH 2 Cl 2中将（diacetoxyiodo ）苯和叔丁基氢过氧化物进行新颖的结合，已实现了3,4-dihydropyrimidin-2（1 H）-ones的干净高效氧化脱氢成1,2-dihydropyrimidines 。
• Novel and Chemoselective Dehydrogenation of 3,4-Dihydropyrimidin-2(1H)-ones with 1,4-Bis(triphenylphosphonium)-2-butene Peroxodisulfate
  作者：Maryam Gorjizadeh

  DOI：10.5012/bkcs.2013.34.6.1751

  日期：2013.6.20

  3,4-Dihydropyrimidin-2(1H)-ones were efficiently converted into the corresponding pyrimidin-2(1H)-ones in high yields within a short period of time on treatment with aqueous acetonitrile using 1,4-bis(triphenylphosphonium)-2-butene peroxodisulfate. Chemoselective oxidation of 3,4-dihydropyrimidin in the presence of other oxidizable functional groups was also achieved by this reagent.

  3,4-二氢嘧啶-2(1H)-酮在1,4-双(三苯基膦)-2-丁烯过硫酸盐水溶液乙腈中处理下，短时间内高效转化为相应的嘧啶-2(1H)-酮，产率很高。该试剂还能在其他可氧化官能团的存在下实现3,4-二氢嘧啶的选择性氧化。
• Palladium-catalyzed dehydrogenation of dihydro-heterocycles using isoprene as the hydrogen acceptor without oxidants
  作者：Xiao-Jun Liu、Wen-Peng Wang、Cong-De Huo、Xi-Cun Wang、Zheng-Jun Quan

  DOI：10.1039/c6cy02038k

  日期：——

  efficient and general method for Pd-catalyzed dehydrogenative aromatization of dihydro-heteroatom compounds without external O2 and H2 is first described. The protocol firstly uses isoprene as a hydrogen acceptor. Various dihydro-heterocycles including dihydropyrimidinones, dihydropyrimidines and dihydropyridines can be dehydrogenated to produce the corresponding aromatic heterocyclic compounds.

  首先描述了在没有外部O 2和H 2的情况下，Pd催化二氢杂原子化合物进行脱氢芳构化的有效方法。该方案首先使用异戊二烯作为氢受体。包括二氢嘧啶酮，二氢嘧啶和二氢吡啶在内的各种二氢杂环可被脱氢以产生相应的芳族杂环化合物。
• Palladium(II) Catalyzed Suzuki/Sonogashira Cross-Coupling Reactions of Sulfonates: An Efficient Approach to C2-Functionalized Pyrimidines and Pyridines
  作者：Zheng-Jun Quan、Fu-Qiang Jing、Zhang Zhang、Yu-Xia Da、Xi-Cun Wang

  DOI：10.1002/ejoc.201300592

  日期：2013.11

  Pyrimidin-2-yl sulfonates, as a reaction partner, can be easily prepared from inexpensive commercial materials and are efficiently cross-coupled with arylboronic acids and terminal alkynes by using Pd(OAc)2-catalyzed Suzuki and Sonogashira reactions. A wide array of C2-functionalized pyrimidines have been prepared in good to excellent yields. 2-Arylpyridines and 2-(oct-1-ynyl)pyridine were also synthesized

  嘧啶-2-基磺酸盐作为反应伙伴，可以从廉价的商业材料中轻松制备，并通过使用 Pd(OAc)2 催化的 Suzuki 和 Sonogashira 反应与芳基硼酸和末端炔烃有效交叉偶联。大量 C2 官能化的嘧啶已经以良好到极好的产率制备。还合成了 2-芳基吡啶和 2-(oct-1-ynyl) 吡啶。
• Synthesis of 2-Substituted Pyrimidines via Cross-Coupling Reaction of Pyrimidin-2-yl Sulfonates with Nucleophiles in Polyethylene Glycol 400
  作者：Xi-Cun Wang、Guo-Jun Yang、Zheng-Jun Quan、Peng-Yan Ji、Jun-Ling Liang、Rong-Guo Ren

  DOI：10.1055/s-0030-1258080

  日期：2010.7

  A mild and rapid procedure to the synthesis of 2-substituted pyrimidines was developed via sequential functionalization of easily available Biginelli 3,4-dihydropyrimidine-2(1H)-ones via oxidation, esterification, followed by cross-coupling reaction of pyrimidin-2-yl sulfonates with N, S, and O nucleophiles in PEG-400 as a green reaction medium at room temperature.

  通过氧化、酯化以及嘧啶-2-的交叉偶联反应对容易获得的 Biginelli 3,4-二氢嘧啶-2(1H)-酮进行顺序功能化，开发了一种温和且快速的合成 2-取代嘧啶的方法在室温下作为绿色反应介质，在 PEG-400 中使用 N、S 和 O 亲核试剂制备基磺酸盐。