1-[4-(3,4-dimethoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl]ethanone

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-[4-(3,4-dimethoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl]ethanone
• 英文别名: 1-[4-(3,4-dimethoxyphenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidin-5-yl]ethanone
• 化学式: C₁₅H₁₈N₂O₃S
• 分子量: 306.386
• InChiKey: MRVWDNAHKCZJAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 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：
  91.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-[4-(3,4-dimethoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl]ethanone 在 劳森试剂 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 20.5h， 生成 (2E)-6-acetyl-2-[6-acetyl-5-(3,4-dimethoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidin-2(3H)-ylidene]-5-(3,4-dimethoxyphenyl)-7-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-3(2H)-one
  参考文献：
  名称：

  Oxidation of thiazolo[3,2-a]pyrimidin-3(2H)-ones with DMSO and Lawesson’s reagent

  摘要：

  2,2'-Dimers with a central double bond were prepared by the oxidation of 5,6-disubstituted 7-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-3(2H)-ones with DMSO and Lawesson's reagent at room temperature. The role of DMSO as an oxidizing reagent was confirmed by NMR spectroscopy. The E-configuration of the central C=C bond for the two diastereomers of compound 8m was proven by single crystal X-ray data. The dimeric thiazolopyrimidines were orange or red colored and absorption bands at 283-330 and 459-476 nm were observed in the UV spectra. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2018.02.014
• 作为产物：
  描述：

  3,4-二甲氧基苯甲醛 、 硫脲 、 乙酰丙酮 在 甲烷磺酸 作用下， 以95%的产率得到1-[4-(3,4-dimethoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl]ethanone
  参考文献：
  名称：

  A Novel Synthesis and Characterization of 1,2,3,4-Tetrahydropyrimidin-2(1H)-thiones

  摘要：

  我们报告了使用布氏酸甲烷磺酸作为促进剂，在 120 ℃ 下进行芳基醛、乙酰丙酮和硫脲的三组分 Biginelli 环缩合反应，从而在短时间内以良好至优异的收率得到相应的 1,2,3,4-四氢嘧啶-2(1H)-硫代化合物。反应高效、简便、快速。通过核磁共振、红外和元素分析，对产物的结构进行了阐释。

  DOI：

  10.14233/ajchem.2017.20346

文献信息

• A Simple and Efficient One-Pot Synthesis of Multifunctional 5-Aryl-<i>5H</i>-thiazolo[3,2-a]pyrimidines
  作者：Seerat Fatima、Anindra Sharma、Rahul Sharma、Rama P. Tripathi

  DOI：10.1002/jhet.831

  日期：2012.5

  One‐pot economical and efficient synthesis of multifunctional 5H‐thiazolo[3,2‐a]pyrimidines by the reaction of 4‐aryl dihydrothiopyrimidines with propargyl bromide in the presence of inorganic base has been reported in very short time.

  据报道，在很短的时间内，可以通过4-芳基二氢硫代嘧啶与炔丙基溴的反应，一锅经济，高效地合成多功能5H-噻唑并[3,2-a]嘧啶。
• El-Hamouly, Wageeh S.; El-Khamry, Abdel-Momen A.; Abbas, Eman M. H., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 9, p. 2091 - 2098
  作者：El-Hamouly, Wageeh S.、El-Khamry, Abdel-Momen A.、Abbas, Eman M. H.

  DOI：——

  日期：——
• Oxidation of thiazolo[3,2-a]pyrimidin-3(2H)-ones with DMSO and Lawesson’s reagent
  作者：Eugenia A. Lashmanova、Anastasiya I. Kirdyashkina、Pavel A. Slepukhin、Andrey K. Shiryaev

  DOI：10.1016/j.tetlet.2018.02.014

  日期：2018.3

  2,2'-Dimers with a central double bond were prepared by the oxidation of 5,6-disubstituted 7-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-3(2H)-ones with DMSO and Lawesson's reagent at room temperature. The role of DMSO as an oxidizing reagent was confirmed by NMR spectroscopy. The E-configuration of the central C=C bond for the two diastereomers of compound 8m was proven by single crystal X-ray data. The dimeric thiazolopyrimidines were orange or red colored and absorption bands at 283-330 and 459-476 nm were observed in the UV spectra. (C) 2018 Elsevier Ltd. All rights reserved.
• A Novel Synthesis and Characterization of 1,2,3,4-Tetrahydropyrimidin-2(1H)-thiones
  作者：N. Krishna Rao、M.S. Surendra Babu、M.V. Basaveswara Rao、Tentu Nageswara Rao、Karri Apprao、G. Kumar

  DOI：10.14233/ajchem.2017.20346

  日期：——

  We reported the use of Brønsted acid methane sulfonic acid as a promoter for three component Biginelli cyclocondensation reaction of aryl aldehydes, acetylacetone and thiourea at 120 °C to afford the corresponding to 1,2,3,4-tetrahydropyrimidin-2(1H)-thiones in good to excellent yields in short span of time. Reaction is efficient, facile and rapid. The structural elucidation of products was done by NMR, IR and elemental analysis.

  我们报告了使用布氏酸甲烷磺酸作为促进剂，在 120 ℃ 下进行芳基醛、乙酰丙酮和硫脲的三组分 Biginelli 环缩合反应，从而在短时间内以良好至优异的收率得到相应的 1,2,3,4-四氢嘧啶-2(1H)-硫代化合物。反应高效、简便、快速。通过核磁共振、红外和元素分析，对产物的结构进行了阐释。