4-(4-chlorophenyl)-1-methyl-3,4,7,8-tetrahydroquinazoline-2,5(1H,6H)-dione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 4-(4-chlorophenyl)-1-methyl-3,4,7,8-tetrahydroquinazoline-2,5(1H,6H)-dione
• 英文别名: 4-(4-chlorophenyl)-1-methyl-4,6,7,8-tetrahydroquinazoline-2,5(1H,3H)-dione；4-(4-chlorophenyl)-1-methyl-4,6,7,8-tetrahydro-3H-quinazoline-2,5-dione
• 化学式: C₁₅H₁₅ClN₂O₂
• 分子量: 290.749
• InChiKey: KKUHWJUFTNKBKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  4-氯苯甲醛 、 1,3-环己二酮 、 N-甲基脲 在 三甲基氯硅烷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以32%的产率得到4-(4-chlorophenyl)-1-methyl-3,4,7,8-tetrahydroquinazoline-2,5(1H,6H)-dione
  参考文献：
  名称：

  An effective Biginelli-type synthesis of 1-methoxy-3,4-dihydropyrimidin-2(1H)-ones

  摘要：

  The ternary condensation of N-methoxyurea, aldehydes, and 1,3-dicarbonyl compounds, resulting in novel 1-methoxy-3,4-dihydropyrimidin-2(1H)-ones has been examined. Commonly used reaction conditions and catalysts (EtOH/HCl, HOAc, DMF) proved to be unsuitable and we found that the DMF-TMSCl system was the best catalyst. Similarly, the reaction of ureas with 4-chlorobenzaldehyde and 1;3-cyclohexanedione using the DMF/TMSCl system afforded 3,4,7,8-tetrahydroquinazolin-2,5(1H,6H)-diones, while other catalyst systems resulted in the formation of product mixtures. In addition, we have developed an effective and simple protocol for the synthesis of N-(methoxy)urea. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2015.06.041

文献信息

• An effective Biginelli-type synthesis of 1-methoxy-3,4-dihydropyrimidin-2(1H)-ones
  作者：Maksim A. Kolosov、Olesia G. Kulyk、Muataz J.K. Al-Ogaili、Valeriy D. Orlov

  DOI：10.1016/j.tetlet.2015.06.041

  日期：2015.8

  The ternary condensation of N-methoxyurea, aldehydes, and 1,3-dicarbonyl compounds, resulting in novel 1-methoxy-3,4-dihydropyrimidin-2(1H)-ones has been examined. Commonly used reaction conditions and catalysts (EtOH/HCl, HOAc, DMF) proved to be unsuitable and we found that the DMF-TMSCl system was the best catalyst. Similarly, the reaction of ureas with 4-chlorobenzaldehyde and 1;3-cyclohexanedione using the DMF/TMSCl system afforded 3,4,7,8-tetrahydroquinazolin-2,5(1H,6H)-diones, while other catalyst systems resulted in the formation of product mixtures. In addition, we have developed an effective and simple protocol for the synthesis of N-(methoxy)urea. (C) 2015 Elsevier Ltd. All rights reserved.