ethyl 6-methyl-4-(2-nitrophenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate | 112080-22-5

• 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 6-methyl-4-(2-nitrophenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: ethyl 4-(2-nitrophenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate；ethyl 6-methyl-4-(2-nitrophenyl)-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate
• CAS: 112080-22-5
• 化学式: C₁₄H₁₅N₃O₄S
• 分子量: 321.357
• InChiKey: YOEWOZKUGHLERD-UHFFFAOYSA-N

物化性质

• 熔点：
  115 °C(Solv: ethanol (64-17-5))
• 沸点：
  443.9±55.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  128
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 6-methyl-4-(2-nitrophenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 在 三氯化铝 、 乙酰氯 作用下， 以 硝基苯 为溶剂， 以45%的产率得到2,3-dihydro-4-methyl-9-nitro-2-thioxo-1H-indeno[1,2-d]pyrimidine-5(9bH)-one
  参考文献：
  名称：

  通过分子内friedel-crafts反应合成一些新颖的稠合的氧代和硫代嘧啶

  摘要：

  1 H-茚并[1,2 - d ]嘧啶-2,5（3 H，9b H）-二酮衍生物2（ai）和2,3-二氢-2-thioxo-1 H-茚并[1,2- d ]嘧啶-5（9b H）-ones 2（jq）是通过分子内的乙基6-甲基-4-芳基-2-芳基-2-氧代-1,2,3的芳基和酯基之间的Friedel-Crafts反应合成的， 4-四氢嘧啶-5-羧酸盐1a-i及其使用AlCl 3的thioxo类似物和乙酰氯在硝基苯中。用THF洗涤后，产物的产率为约45-69％。IR和NMR光谱以及元素分析被用于鉴定这些化合物。

  DOI：

  10.1002/jhet.5570440309
• 作为产物：
  描述：

  1,4-dihydro-2-[[(4-methoxyphenyl)methyl]thio]-6-methyl-4-(2-nitrophenyl)-5-pyrimidinecarboxylic acid, ethyl ester 在 三氟乙酸 、 乙硫醇 作用下， 以 四氢呋喃 为溶剂， 生成 ethyl 6-methyl-4-(2-nitrophenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  Atwal, Karnail S.; O'Reilly, Brian C.; Gougoutas, Jack Z., Heterocycles, 1987, vol. 26, # 5, p. 1189 - 1192

  摘要：

  DOI：

文献信息

• A domino desulfurative coupling–acylation–hydration–Michael addition process for the synthesis of polysubstituted tetrahydro-4H-pyrido[1,2-a]pyrimidines
  作者：Zhong-Fei Yan、Zheng-Jun Quan、Yu-Xia Da、Zhang Zhang、Xi-Cun Wang

  DOI：10.1039/c4cc05090h

  日期：——

  A novel method for the synthesis of the polysubstituted tetrahydro-4H-pyrido[1,2-a]pyrimidines through a domino desulfurative coupling–acylation–hydration and Michael addition sequence was established.

  建立了一种通过多米诺脱硫偶联-酰化-水合和迈克尔加成序列合成多取代四氢-4H-吡啶并[1,2-a]嘧啶的新方法。
• An Efficient Synthesis of Some Novel Bicyclic Thiazolopyrimidine Derivatives
  作者：Akbar Mobinikhaledi、Mojgan Zendehdel、Mahdia Hamidi Nasab、Mohammad Ali Bodaghi Fard

  DOI：10.1515/hc.2009.15.6.451

  日期：2009.1

  An efficient and rapid synthesis of some thiazolopyrimidine derivatives from pyrimidinthiones and chloroacetyl chloride in refluxing tetrahydrofurane (THF) is described. The method is simple and practical, and generating thiazole derivatives in good isolated yields.

  描述了在回流四氢呋喃 (THF) 中由嘧啶硫酮和氯乙酰氯高效快速合成一些噻唑并嘧啶衍生物。该方法简单实用，生成的噻唑衍生物分离收率良好。
• Ionic liquid-assisted synthesis of dihydropyrimidin(thi)one Biginelli adducts and investigation of their mechanism of urease inhibition
  作者：Taniris Cafiero Braga、Thamara Ferreira Silva、Thamilla Maria Silva Maciel、Edjan Carlos Dantas da Silva、Edeildo Ferreira da Silva-Júnior、Luzia Valentina Modolo、Isis Martins Figueiredo、Josué Carinhanha Caldas Santos、Thiago Mendonça de Aquino、Ângelo de Fátima

  DOI：10.1039/c9nj03556g

  日期：——

  Twenty-six Biginelli adducts were synthesized through an ionic liquid-assisted synthesis with up to 92% yield. Sixteen of these Biginelli adducts were then assayed to determine their antiureolytic activity against purified urease from jack beans. The substances BA7-S, BA9-S and BA11-S were shown to be as efficient inhibitors as hydroxyurea, a positive control used in in vitro screening assay against

  通过离子液体辅助合成法合成了26种Biginelli加合物，收率高达92％。然后分析这些Biginelli加合物中的16种，以确定它们对来自千斤顶豆的纯化脲酶的抗脲水解活性。物质BA7-S，BA9-S和BA11-S被证明是与羟基脲有效的抑制剂，羟基脲是用于体外抗脲酶筛选试验的阳性对照。荧光研究表明，BA7-S，BA9-S，BA11-S和BA5-S分别具有5.95、6.72、4.55和4.28 M -1的高结合常数，而BAS12-S无取代基的log K b = 2.16 M -1的值低 。另外，在最热力学上有利的BA5-S和BA7-S脲酶复合物中，相应的Biginelli加合物能够通过非离子相互作用（例如疏水相互作用或氢和范德华相互作用）与脲酶的活性位点相互作用， 分别。计算机分析研究还支持BA与活性位点相互作用，从而证实了荧光和动力学分析研究，这清楚表明BA5-S和BA7-S是竞争性抑制剂（K
• Solvent-free efficient one-pot synthesis of Biginelli and Hantzsch compounds catalyzed by potassium phthalimide as a green and reusable organocatalyst
  作者：Hamzeh Kiyani、Maryam Ghiasi

  DOI：10.1007/s11164-014-1621-x

  日期：2015.8

  The usage of potassium phthalimide (PPI) for the simple and green one-step multicomponent synthesis of Hantzsch 1,4-dihydropyridines, polyhydroquinolines, 3,4-dihydropyrimidin-2(1H)-ones/thiones, and octahydroquinazolinones under solventless conditions at 120 °C is reported. The method is operationally simple, environmentally benign, and has relatively high yields. The other merits of this method include efficient, clean, green, and catalyst reusability.

  本文报道了在无溶剂条件下，于120°C下使用邻苯二甲酰亚胺钾（PPI）进行Hantzsch 1,4-二氢吡啶、多氢喹啉、3,4-二氢嘧啶-2(1H)-酮/硫酮以及八氢喹唑啉酮的一步多组分简单绿色合成。该方法操作简便，环境友好，且产率相对较高。此外，该方法还具有高效、清洁、绿色以及催化剂可重复使用的优点。
• New magnetic nanocomposites of ZrO₂–Al₂O₃–Fe₃O₄as green solid acid catalysts in organic reactions
  作者：Anqi Wang、Xiang Liu、Zhongxing Su、Huanwang Jing

  DOI：10.1039/c3cy00572k

  日期：——

  A series of magnetic solid acid nano-catalysts were designed and prepared through a facile co-precipitate approach. The original nanocomposites ZrO2–Al2O3–Fe3O4 were characterized by means of ICP-AES, BET, XRD, TEM, HRTEM, VSM, FT-IR, NH3-TPD and TG. Their catalytic behaviours were investigated via esterification, the synthesis of bis-indolylmethanes, Hantzsch reaction, Biginelli reaction and Pechmann reaction. In all of these organic reactions, the corresponding products were obtained in moderate to excellent yields. The optimal catalyst was ZAF-16/16, which retained catalytic activity after several recycles.

  通过简便的共沉淀方法设计并制备了一系列磁性固体酸纳米催化剂。原始纳米复合材料ZrO2–Al2O3–Fe3O4通过ICP-AES、BET、XRD、TEM、HRTEM、VSM、FT-IR、NH3-TPD和TG进行了表征。通过酯化反应、双吲哚甲烷合成、Hantzsch反应、Biginelli反应和Pechmann反应研究了它们的催化行为。在所有这些有机反应中，获得了相应产品的中等至优良产率。最佳催化剂是ZAF-16/16，经过多次循环后仍保持催化活性。