methyl 6-methyl-4-styryl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate | 302821-61-0

• 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: methyl 6-methyl-4-styryl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: 5-ethoxycarbonyl-6-methyl-4-styryl-3,4-dihydropyrimidin-2(1H)-thione；1,2,3,4-tetrahydro-6-methyl-4-(2-phenylethenyl)-2-thioxo-5-pyrimidinecarboxylic acid methyl ester；methyl 6-methyl-4-(2-phenylethenyl)-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate
• CAS: 302821-61-0
• 化学式: C₁₅H₁₆N₂O₂S
• 分子量: 288.37
• InChiKey: ZRYVNDFNDNKVOP-UHFFFAOYSA-N

物化性质

• 沸点：
  410.1±55.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  82.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  乙酰乙酸甲酯 、 硫脲 、 肉桂醛 在 1,8-diazabicyclo[5.4.0]-7-undecenium 2-methylimidazolide 作用下， 以88%的产率得到methyl 6-methyl-4-styryl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  DBU-MIm coupled ionic liquids as reusable catalysts for the Biginelli reaction

  摘要：

  DOI：

  10.1016/j.mcat.2022.112906

文献信息

• Zeolite catalyzed solvent-free one-pot synthesis of dihydropyrimidin-2(1<i>H</i>)-ones – A practical synthesis of monastrol
  作者：Mukund G Kulkarni、Sanjay W Chavhan、Mahadev P Shinde、Dnyaneshwar D Gaikwad、Ajit S Borhade、Attrimuni P Dhondge、Yunnus B Shaikh、Vijay B Ningdale、Mayur P Desai、Deekshaputra R Birhade

  DOI：10.3762/bjoc.5.4

  日期：——

  A zeolite-catalyzed, simple, one-pot, solvent-free, cost effective, and environmentally benign process for the synthesis of dihydropyrimidones is described. This reaction is scaleable to multigram scale and the catalyst is recyclable. This methodology has resulted in an efficient synthesis of monastrol, a potent inhibitor of kinesin Eg5.

  描述了一种沸石催化、简单、单锅、无溶剂、成本有效且环境友好的合成二氢嘧啶酮的方法。该反应可扩展到数克规模，并且催化剂可回收利用。这种方法导致了monastrol的有效合成，monastrol是驱动蛋白Eg5的有效抑制剂。
• Ultrasound-Mediated Synthesis of 3,4-Dihydropyrimidin-2-(<i>1H</i>)-Ones (or Thiones) with NaHSO₄·H₂O
  作者：Karim Akbari Dilmaghani、Behzad Zeynizadeh、Maryam Amirpoor

  DOI：10.1080/10426507.2013.777725

  日期：2013.11.1

  A fast and efficient Biginelli synthesis of 3,4-dihydropyrimidin-2-(1H)-ones (or thiones) by the reaction of aromatic aldehydes, -dicarbonyls, and urea/thiourea using NaHSO4H2O/ultrasound system is presented. The reactions were carried out in refluxing n-hexane/CH3CN (2.5:0.5mL) to afford the products in excellent yields.
• DBU-MIm coupled ionic liquids as reusable catalysts for the Biginelli reaction
  作者：Monika Sharma、Khushboo Verma、Ajeet Kaushik、Jasminder Singh、Avtar Singh、Rahul Badru

  DOI：10.1016/j.mcat.2022.112906

  日期：2023.2