5-methylmercaptothiocarbonyl-4-(4-methoxyphenyl)-6-phenyl-3,4-dihydropyrimidin-2(1H)-one | 1142124-45-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-methylmercaptothiocarbonyl-4-(4-methoxyphenyl)-6-phenyl-3,4-dihydropyrimidin-2(1H)-one
• 英文别名: methyl 4-(4-methoxyphenyl)-2-oxo-6-phenyl-3,4-dihydro-1H-pyrimidine-5-carbodithioate
• CAS: 1142124-45-5
• 化学式: C₁₉H₁₈N₂O₂S₂
• 分子量: 370.496
• InChiKey: SYVMZWAQZMBHQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  苯乙酮 在 SiO₂*ZnCl₂ 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 5-methylmercaptothiocarbonyl-4-(4-methoxyphenyl)-6-phenyl-3,4-dihydropyrimidin-2(1H)-one
  参考文献：
  名称：

  二氧化硅-ZnCl2：一种高效且可重复使用的固体催化剂，可在无溶剂条件下一锅合成5-甲基巯基硫代羰基-4-芳基-3-二氢嘧啶-2（1H）-酮。

  摘要：

  本报告介绍了二氧化硅-ZnCl 2的合成应用，这是一种高效且环保的催化剂，用于合成小分子二氢嘧啶酮。该反应涉及在无溶剂条件下进行一锅多组分的β-氧二硫代羧酸盐，醛和尿素的反应。实验过程简单，对环境无害，可耐受许多官能团，并能产生良好或极好的产品收率。

  DOI：

  10.1002/bkcs.10606

文献信息

• Application of β-Oxodithioesters in Domino and Multicomponent Reactions: Facile Route to Dihydropyrimidines and Coumarins
  作者：Okram Mukherjee Singh、Nepram Sushuma Devi

  DOI：10.1021/jo802585b

  日期：2009.4.17

  A facile route to hitherto unknown 5-methylmercaptothio-carbonyl-4-aryl-3,4-dihydropyrimidin-2(1H)-ones and substituted 2H-chromene-2-thiones has been developed. SnCl2 catalyzed cyclocondensation of beta-oxodithioesters with a variety of readily accessible aldehydes and urea affords the dihydropyrimidinones. The methodology involves the three-component Biginelli reaction. On the other hand, substituted salicylaldehyde and beta-oxodithioesters reacted under the same condition to afford the substituted 2H-chromene-2-thiones in high yields.
• Biginelli and Hantzsch-Type Reactions Leading to Highly Functionalized Dihydropyrimidinone, Thiocoumarin, and Pyridopyrimidinone Frameworks via Ring Annulation with β-Oxodithioesters
  作者：Ganesh Chandra Nandi、Subhasis Samai、Maya Shankar Singh

  DOI：10.1021/jo101572c

  日期：2010.11.19

  An efficient and highly convergent route to dihydropyrimidinones (DHPMs) and hitherto unreported dihydropyridopyrimidinones has been developed by one-pot, three-component cyclocondensation of aromatic aldehydes, beta-oxodithioesters, and urea/6-amino-1,3-dimethyluracil in the presence of recyclable SiO2-H2SO4 On the other hand, salicylaldehyde, beta-oxodithioester, and urea reacted under similar conditions to afford the 3-aroyl/heteroaroyl-2H-chromen-2-thiones in high yields instead of Biginelli product The attractive feature of this approach is the synthesis of three important bioactive heterocyclic frameworks from the same beta-oxodithioester under the similar reaction conditions, making this new strategy highly useful in diversity-oriented synthesis (DOS)