ethyl 4-(furan-2-yl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylate | 123629-45-8

• 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-(furan-2-yl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylate
• 英文别名: (±)-ethyl 4-(furan-2-yl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate；ethyl 4-(furan-2-yl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate
• CAS: 123629-45-8
• 化学式: C₁₂H₁₄N₂O₃S
• 分子量: 266.321
• InChiKey: ZMMCCRDZRJWDQX-UHFFFAOYSA-N

物化性质

• 熔点：
  186-188 °C(Solv: ethyl acetate (141-78-6); ligroine (8032-32-4))
• 沸点：
  369.3±52.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)
• 溶解度：
  39.9 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  95.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 4-(furan-2-yl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylate 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 0.42h， 生成 ethyl 9-(furan-2-yl)-7-methyl-2,4-dithioxo-2,3,4,9-tetrahydro-1H-thiazolo[3,2-a:4,5-d']dipyrimidine-8-carboxylate
  参考文献：
  名称：

  一些具有潜在抗氧化和抗菌活性的新型噻唑并嘧啶、噻唑二嘧啶和噻唑并嘧啶并噻唑并嘧啶衍生物的微波辅助合成

  摘要：

  乙酰乙酸乙酯、硫脲和适当的芳香醛的 Biginelli 反应用于生产 4-aryl-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylates，它与溴丙二腈反应生成得到 3-氨基-5-芳基-2-氰基-7-甲基-5H-噻唑并[3,2-a]嘧啶-6-羧酸乙酯，而不是异构的7H-噻唑并[3,2-a]嘧啶。噻唑并嘧啶衍生物与二硫化碳反应生成乙基 9-芳基-7-甲基-2,4-二硫代-2,3,4,9-四氢-1H-噻唑并[3,2-a:4,5-d'] dipyrimidine-8-carboxylates，与苯甲酰溴反应生成乙基 8-methyl-10-(4-methoxyphenyl)-3-located-5-thioxo-2(un)subatituded-10H-thiazolo[3'',2' ':1',2']pyrimido[4',5':4

  DOI：

  10.3390/molecules17089652
• 作为产物：
  描述：

  D-木糖 在 Fe₃O₄/SiO₂-SO₃H 作用下， 以 水 为溶剂， 反应 5.5h， 生成 ethyl 4-(furan-2-yl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylate
  参考文献：
  名称：

  Dehydration of Xylose to Furfural and Its Valorization via Different Multicomponent Reactions Using Sulfonated Silica with Magnetic Properties as Recyclable Catalyst

  摘要：

  Sulfonated silica with magnetic properties was studied for dehydration of xylose to furfural and posteriorly for furfural valorization through the Biginelli and Hantzsch multicomponent reactions. Eleven polysubstituted heterocycles were obtained in excellent yields and without any side-product (81-91 %), using a multicomponent green methodology. The presence of Fe3O4 particles allows an easy separation from the reaction medium giving a high yield in the reusability studies.

  DOI：

  10.1007/s10562-014-1267-8

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。
• A novel one pot synthesis of nitrogen containing heterocycles: an alternate methodology to the Biginelli and Hantzsch reactions
  作者：Mazaahir Kidwai、Shilpi Saxena、Richa Mohan、R. Venkataramanan

  DOI：10.1039/b205539m

  日期：——

  Modified Biginelli and Hantzsch reactions were carried using environmentally benign processes. Neat reactants subjected to microwave radiation gave the required products more quickly and in better yields in comparison to traditional methodologies. The observed yields and enhancement in reaction rates are due to the solvent free conditions coupled with the use of microwave radiation.

  使用环境友好的工艺进行了改良的Biginelli反应和Hantzsch反应。采用无溶剂的原料并施加微波辐射，相较于传统方法，能更快地获得所需产品，且产率更佳。观察到的产率提高和反应速率加速，是由于采用了无溶剂条件并结合了微波辐射技术。
• The Biginelli Reaction with an Imidazolium-Tagged Recyclable Iron Catalyst: Kinetics, Mechanism, and Antitumoral Activity
  作者：Luciana M. Ramos、Bruna C. Guido、Catharine C. Nobrega、José R. Corrêa、Rafael G. Silva、Heibbe C. B. de Oliveira、Alexandre F. Gomes、Fábio C. Gozzo、Brenno A. D. Neto

  DOI：10.1002/chem.201204314

  日期：2013.3.25

  The present work describes the synthesis, characterization, and application of a new ion‐tagged iron catalyst. The catalyst was employed in the Biginelli reaction with impressive performance. High yields have been achieved when the reaction was carried out in imidazolium‐based ionic liquids (BMI⋅PF6, BMI⋅NTf2, and BMI⋅BF4), thus showing that the ionic‐liquid effects play a role in the reaction. Moreover

  本工作描述了新型离子标记铁催化剂的合成，表征和应用。该催化剂用于Biginelli反应中，具有令人印象深刻的性能。当反应在咪唑鎓基的离子液体进行（BMI高的产率已经达到⋅ PF 6，BMI ⋅ NTF 2，和BMI ⋅ BF 4），因此表明离子液体效应在反应中起作用。此外，离子标记的催化剂可以回收并重复使用多达八次，而活性没有任何明显的损失。通过使用高分辨率电喷雾电离四极杆飞行时间质谱（HR-EI-QTOF）光谱和动力学实验进行的机理研究表明，只有一种反应途径可以排除发展条件下的其他两种可能性。理论计算符合所提出的铁催化剂的作用机理。最后，Biginelli反应的产物37种二氢嘧啶酮衍生物在针对MCF-7癌细胞线的测定中评估了其细胞毒性，并获得了令人鼓舞的结果，其中某些衍生物对健康细胞线（成纤维细胞）几乎无毒。
• Design, Synthesis and Antiproliferative Activities Evaluation of Thiazolopyrimidines Derivatives through Biginelli Reaction
  作者：Pengju Zhu、Huansheng Fu、Hao Fang

  DOI：10.2174/1570180814666170512123132

  日期：2017.10.31

  biological activity. Up to date, thiazolopyrimidines derivatives have widespread applications in pharmaceutical fields. In this article, a series of thiazolopyrimidine derivatives were designed based on the lead compound structure in our previous studies. Methods: All the target compounds were synthesized with the coupling reaction, Biginelli reaction and “one-pot” aldol condensation. Their structures

  背景：噻唑并嘧啶具有其结构多样性和多种生物学活性。迄今为止，噻唑并嘧啶衍生物已在制药领域中广泛应用。在本文中，我们在先前的研究中基于铅化合物的结构设计了一系列噻唑并嘧啶衍生物。 方法：通过偶联反应，Biginelli反应和“一锅法”羟醛缩合反应合成所有目标化合物。它们的结构通过1 H NMR，13 C NMR光谱和HRMS鉴定。通过MTT评估目标化合物的抗肿瘤活性。 结果：合成了25种新的目标化合物，主要是通过测试它们对两种人类肿瘤细胞系的抑制率进行筛选，化合物15、17、20、22、40对MDA-MB-231和K562的抑制率均超过70％ 。进一步评估它们针对五种肿瘤细胞系的IC50，15和22在MDAMB-231，K562和PC-3中显示出优于先导化合物I的优势。 结论：合成了一系列噻唑并嘧啶衍生物，初步的生物学评估表明，目标化合物22对棉铃虫K562的抗增殖活性优于棉酚。
• Natural Organic Acids Promoted Synthesis of 3, 4-Dihydropyrimidin- 2(1H)-ones/thiones Under Solvent-free Conditions
  作者：Nitin Thorat、Shankar Thopate

  DOI：10.2174/1570178612666150108003629

  日期：2015.3.3

  Naturally occurring organic acids are reported to be highly efficient promoters for the Biginelli reaction under thermal and microwave irradiation using solvent free conditions. Among the various organic acids used, malic acid was found to be the most effective promoter for Biginelli reaction under above reaction conditions. Present protocol is a simple and eco-friendly route for the synthesis of 3, 4-dihydropyrimidin-2(1H)-ones/thiones.

  自然发生的有机酸被报道在无溶剂条件下，在热和微波照射下对Biginelli反应具有高效促进作用。在所使用的各种有机酸中，苹果酸被发现是上述反应条件下对Biginelli反应最有效的促进剂。目前的协议是一种简单且环保的合成3, 4-二氢吡啶-2(1H)-酮/硫酮的方法。