1,2,3,4-tetrahydro-4-(4-methoxyphenyl)-6-phenyl-2-thioxo-5-pyrimidinecarboxylic acid ethyl ester

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: 1,2,3,4-tetrahydro-4-(4-methoxyphenyl)-6-phenyl-2-thioxo-5-pyrimidinecarboxylic acid ethyl ester
• 英文别名: ethyl 4-(4-methoxyphenyl)-6-phenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate；ethyl 4-(4'-methoxyphenyl)-6-phenyl-3,4-dihydropyrimidin-2(1H)-thione-5-carboxylate；ethyl 4-(4-methoxyphenyl)-6-phenyl-2-thioxo-3,4-dihydro-1H-pyrimidine-5-carboxylate；ethyl 4-(4-methoxyphenyl)-6-phenyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate
• 化学式: C₂₀H₂₀N₂O₃S
• 分子量: 368.456
• InChiKey: DUVGSKAVFBGUSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 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：
  91.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetrahydro-4-(4-methoxyphenyl)-6-phenyl-2-thioxo-5-pyrimidinecarboxylic acid ethyl ester 在 哌啶 、 sodium acetate 、 乙酸酐 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 10.0h， 生成 ethyl 2-[[4-(2-methoxy-2-oxoethoxy)phenyl]methylidene]-5-(4-methoxyphenyl)-3-oxo-7-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
  参考文献：
  名称：

  Thiazolidione derivatives as novel antibiofilm agents: Design, synthesis, biological evaluation, and structure–activity relationships

  摘要：

  Rational designed novel thiazolidiones were synthesized and evaluated for antibiofilm activity. The active derivatives were not only potent inhibitors of Staphylococcus epidermidis biofilm growth but also efficient antibacterial agents. 3f showed 4-fold higher activity (6.25 mu M) in the biofilms dispersal assay and significantly higher antibacterial activity (MIC 3.125 mu M) in comparison to the 3-(5-((6- (ethoxycarbonyl)-5-(benzo[1,3]dioxol-5-yl)-3-oxo-7-phenyl- thiazolo[3,2-a]pyrimidin-2(5H)-ylidene)methyl) furan-2-yl)benzoic acid (1). (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.12.014
• 作为产物：
  描述：

  苯甲酰乙酸乙酯 、 4-甲氧基苯甲醛 、 硫脲 以 乙醇 为溶剂， 反应 3.0h， 生成 1,2,3,4-tetrahydro-4-(4-methoxyphenyl)-6-phenyl-2-thioxo-5-pyrimidinecarboxylic acid ethyl ester
  参考文献：
  名称：

  作为新型乙酰胆碱酯酶抑制剂的稠合噻唑并 [3,2-a] 嘧啶的合成、晶体结构和生物学评价

  摘要：

  从 3,4-二氢嘧啶硫酮前体合成了一系列新的噻唑并 [3,2-a] 嘧啶溴化物盐衍生物 7a-d。目标化合物通过一维和二维核磁共振、高分辨率 ESI-MS/MS 和单晶 X 射线衍射分析进行了全面表征，证实了二氢嘧啶硫酮的区域选择性 5H 环化。所有目标化合物都通过基于 Ellman 的比色法在体外评估为人乙酰胆碱酯酶 (hAChE) 抑制剂，并显示出良好的抑制活性（10 µM 时优于 70%，IC50 值在 1 µM 范围内）。对所有目标产物进入 hAChE 进行了分子对接模拟，并证实了与酶的强结合。

  DOI：

  10.3390/molecules24122306

文献信息

• Synthesis of 2-substituted pyrimidines and benzoxazoles via a visible-light-driven organocatalytic aerobic oxidation: enhancement of the reaction rate and selectivity by a base
  作者：Lin Wang、Zhi-Gang Ma、Xiao-Jing Wei、Qing-Yuan Meng、Deng-Tao Yang、Shao-Fu Du、Zi-Fei Chen、Li-Zhu Wu、Qiang Liu

  DOI：10.1039/c4gc00337c

  日期：——

  An efficient visible-light-driven photocatalytic oxidation of various 2-substituted dihydropyrimidines and phenolic imines has been achieved using an organic photocatalyst eosin Y bis(tetrabutyl ammonium salt) (TBA-eosin Y) and inexpensive oxidant molecular oxygen. With the aid of a base, significantly enhanced photoinduced electron transfer from substrates dihydropyrimidines or phenolic imines to the excited state of TBA-eosin Y has enabled the aerobic oxidation to yield 2-(methylthio)pyrimidines or 2-arylbenzoxazoles selectively.

  利用有机光催化剂藻红Y双(四丁基铵盐)(TBA-藻红Y)和廉价氧化剂分子氧，已经实现了各种2-取代二氢嘧啶和酚亚胺的高效可见光驱动光催化氧化反应。在碱的辅助下，从底物二氢嘧啶或酚亚胺到TBA-藻红Y激发态的显著增强的光诱导电子转移，使得空气氧化能够选择性地生成2-(甲硫基)嘧啶或2-芳基苯并噁唑。
• Oxidative transformation of thiols to disulfides promoted by activated carbon–air system
  作者：Masahiko Hayashi、Ken-ichi Okunaga、Shunsuke Nishida、Kenjiro Kawamura、Kazuo Eda

  DOI：10.1016/j.tetlet.2010.10.070

  日期：2010.12

  Efficient oxidative transformation of thiols to disulfides took place in the presence of activated carbon under an oxygen (or air) atmosphere. The present oxidation method is available not only for a variety of thiols such as simple aromatic and aliphatic thiols but also for 3,4-dihydropyrimidin-2(1H)-thiones and N-Boc-l-cysteine.

  在氧气（或空气）气氛下，在存在活性炭的情况下，硫醇进行了有效的氧化转化为二硫化物。本氧化方法不仅可用于多种硫醇，例如简单的芳族和脂族硫醇，而且可用于3,4-二氢嘧啶-2（1 H）-硫酮和N- Boc- 1-半胱氨酸。
• Aerobic copper-promoted oxidative dehydrosulfurative carbon–oxygen cross-coupling of 3,4-dihydropyrimidine-1<i>H</i>-2-thiones with alcohols
  作者：Jihong Lee、Yujeong Kwon、Dong-Chan Lee、Jeong-Hun Sohn

  DOI：10.1039/d1ra07713a

  日期：——

  A wide range of readily available DHPMs and alcohols makes the presented reaction an attractive method to access biologically valuable 2-alkoxypyrimidine derivatives with rapid diversification.

  一系列易得的DHPMs和醇使得所呈现的反应成为一种吸引人的方法，可用于快速多样化地获得具有生物学价值的2-烷氧基嘧啶衍生物。
• Dehydrosulfurative C–N Cross-Coupling and Concomitant Oxidative Dehydrogenation for One-Step Synthesis of 2-Aryl(alkyl)aminopyrimidines from 3,4-Dihydropyrimidin-1<i>H</i>-2-thiones
  作者：Nguyen Huu Trong Phan、Hyeji Kim、Hyunik Shin、Hee-Seung Lee、Jeong-Hun Sohn

  DOI：10.1021/acs.orglett.6b02617

  日期：2016.10.7

  A method for the synthesis of 2-aryl(alkyl)aminopyrimidines from readily available 3,4-dihydropyrimidin-1H-2-thiones (DHPMs) via dehydrosulfurative C–N cross-coupling and concomitant oxidative dehydrogenation under a Pd/Cu catalytic system is described. This reaction protocol provides unprecedented diversity of fully substituted 2-aryl(alkyl)aminopyrimidines in a single step from a wide range of DHPMs

  一种在Pd / Cu催化体系下通过脱硫C–N交叉偶联和伴随的氧化脱氢从容易获得的3,4-二氢嘧啶-1 H -2-硫酮（DHPM）合成2-芳基（烷基）氨基嘧啶的方法描述。该反应方案只需一步即可从多种DHPM和胺偶联伙伴中提供前所未有的完全取代的2-芳基（烷基）氨基嘧啶多样性。
• Boric Ester and Thiourea as Coupling Partners in a Copper-Mediated Oxidative Dehydrosulfurative Carbon–Oxygen Cross-Coupling Reaction
  作者：Hyeji Kim、Jihong Lee、Hyunik Shin、Jeong-Hun Sohn

  DOI：10.1021/acs.orglett.8b00502

  日期：2018.4.6

  dehydrosulfurative carbon–oxygen cross-coupling reaction with boric ester and six-membered cyclic thiourea for single-step production of densely substituted 2-alkoxypyrimidines incorporated in a privileged scaffold is described. This is the first demonstration of boric ester acting as an alkoxy donor in a metal-catalyzed coupling reaction to produce ether. The reaction method offers a shortcut for producing

  描述了一种与硼酸酯和六元环硫脲进行铜介导的氧化脱氢硫碳-氧交叉偶联反应，用于一步制备高密度取代的2-烷氧基嘧啶的方法，该方法被并入了优先的支架中。这是硼酸酯在金属催化的偶合反应中生成醚的过程中首次证明烷氧基供体。该反应方法为快速多样化生产2-烷氧基嘧啶衍生物提供了捷径，并扩大了硼酸酯的应用范围和Liebeskind-Srogl型反应的范围。