5-acetyl-4-(2-methoxyphenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-thione | 292878-49-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-acetyl-4-(2-methoxyphenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-thione
• 英文别名: 5-acetyl-6-methyl-4-(2-methoxylphenyl)-3,4-dihydropyrimidine-2(1H)-thione；1-[4-(2-methoxyphenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidin-5-yl]ethanone
• CAS: 292878-49-0
• 化学式: C₁₄H₁₆N₂O₂S
• 分子量: 276.359
• InChiKey: FBZHEUZWTKOZPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  82.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-acetyl-4-(2-methoxyphenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-thione 在 劳森试剂 、 二甲基亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 16.5h， 生成 (2E)-6-acetyl-2-[6-acetyl-5-(2-methoxyphenyl)-7-methyl-3-oxo-5H-[1,3]thiazolo[3,2-a]pyrimidin-2(3H)-ylidene]-5-(2-methoxyphenyl)-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：

  硫脲 、 邻甲氧基苯甲醛 、 乙酰丙酮 在 tungstate sulfuric acid 作用下， 以82%的产率得到5-acetyl-4-(2-methoxyphenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-thione
  参考文献：
  名称：

  使用钨酸盐硫酸 (TSA) 作为可回收催化剂的一锅法合成二氢嘧啶-硫酮衍生物

  摘要：

  摘要 一种高效、简单且环境友好的 3,4-二氢嘧啶-2-(1H) 硫酮衍生物的一锅法合成方法，该方法需要适当的芳基醛、β-二羰基和硫脲的三组分缩合反应。据报道，在无溶剂条件下存在催化量的钨酸硫酸。该方法具有收率高、反应时间短、后处理简单等优点。补充材料可用于本文。访问出版商的在线版磷、硫和硅及相关元素，获取以下免费补充资源：5b、5g、5j、5i、5l (S2-S16) 的 1H、13C NMR 和质谱。附加特征数据 (S17-18)。图形概要

  DOI：

  10.1080/10426507.2011.616562

文献信息

• Tetrachlorosilane catalyzed multicomponent one-step fusion of biopertinent pyrimidine heterocycles
  作者：Chennan Ramalingan、Young-Woo Kwak

  DOI：10.1016/j.tet.2008.03.078

  日期：2008.5

  Multicomponent one-step fusion of a variety of pharmacologically pertinent pyrimidine heterocycles has efficiently been achieved from their respective aldehydes, beta-dicarbonyl compounds, and urea/thiourea in the presence of a catalytic amount of tetrachlorosilane in DMF/AN mixture at normal ambient temperature. (C) 2008 Elsevier Ltd. All rights reserved.
• 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.
• One-Pot Synthesis of Dihydropyrimidine-Thione Derivatives Using Tungstate Sulfuric Acid (TSA) as a Recyclable Catalyst
  作者：Bahador Karami、Zahra Haghighijou、Mahnaz Farahi、Saeed Khodabakhshi

  DOI：10.1080/10426507.2011.616562

  日期：2012.6

  Abstract An efficient, simple, and environmentally benign procedure for the one-pot synthesis of 3,4-dihydropyrimidine-2-(1H) thione derivatives that entails the three-component condensation of appropriate aryl aldehydes, β-dicarbonyls, and thiourea in the presence of catalytic amount of tungstate sulfuric acid under solvent-free conditions was reported. This method has many advantages including excellent

  摘要 一种高效、简单且环境友好的 3,4-二氢嘧啶-2-(1H) 硫酮衍生物的一锅法合成方法，该方法需要适当的芳基醛、β-二羰基和硫脲的三组分缩合反应。据报道，在无溶剂条件下存在催化量的钨酸硫酸。该方法具有收率高、反应时间短、后处理简单等优点。补充材料可用于本文。访问出版商的在线版磷、硫和硅及相关元素，获取以下免费补充资源：5b、5g、5j、5i、5l (S2-S16) 的 1H、13C NMR 和质谱。附加特征数据 (S17-18)。图形概要