ethyl 1-benzyl-4-(4-chlorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

• 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: ethyl 1-benzyl-4-(4-chlorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: 1-benzyl-4-(4'-chlorophenyl)-5-ethoxycarbonyl-6-methyl-3,4-dihydropyrimidin-2(1H)-one；Ethyl 3-benzyl-6-(4-chlorophenyl)-4-methyl-2-oxo-1,6-dihydropyrimidine-5-carboxylate
• 化学式: C₂₁H₂₁ClN₂O₃
• 分子量: 384.862
• InChiKey: SNKIKQRMTWLHSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N,N'-(4-chloro-benzylidene)-bis-carbamic acid diethyl ester 在 五氯化磷 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 6.0h， 生成 ethyl 1-benzyl-4-(4-chlorophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  通过 α-氯苄基异氰酸酯与 N-烷基（芳基）-β-氨基巴豆酸乙酯的环缩合反应方便地合成 N1-取代的 3,4-二氢嘧啶-2（1H）-酮

  摘要：

  使用 α-氯苄基异氰酸酯与 N-烷基（芳基）-β-氨基巴豆酸乙酯的区域选择性环缩合反应，开发了一种合成 N1 取代的 3,4-二氢嘧啶-2(1H)-酮的新方法。以高收率制备了许多通过其他方法难以获得的 N1-芳基和 N1-烷基取代的 Biginelli 化合物。

  DOI：

  10.1055/s-2006-926241

文献信息

• N-Substituted Ureas and Thioureas in Biginelli Reaction Promoted by Chlorotrimethylsilane: Convenient Synthesis of <i>N</i>1-Alkyl-, <i>N</i>1-Aryl-, and <i>N</i>1,<i>N</i>3-Dialkyl-3,4-Dihydropyrimidin-2(1<i>H</i>)-(thi)ones
  作者：Dmitriy Volochnyuk、Sergey Ryabukhin、Andrey Plaskon、Eugeniy Ostapchuk、Andrey Tolmachev

  DOI：10.1055/s-2007-965881

  日期：2007.2

  The classical Biginelli reaction has been extended by the use of N-substituted ureas and thioureas. A set of N1-alkyl-, N1-aryl-, and N1,N3-dialkyl-3,4-dihydropyrimidin-2(1H)-(thi)ones was readily prepared in excellent yield when chlorotrimethylsilane in N,N-dimethylformamide was used as promoter and water scavenger.

  经典的Biginelli反应已经通过使用N取代的尿素和硫尿素得到了扩展。当在N,N-二甲基甲酰胺中使用氯三甲基硅烷作为促进剂和脱水剂时，能够容易地以优异的产率合成一系列N1-烷基、N1-芳基和N1,N3-双烷基-3,4-二氢嘧啶-2(1H)-(硫)酮。
• Regioselective N1-alkylation of 3,4-dihydropyrimidine-2(1H)-ones: Screening of their biological activities against Ca2+-ATPase
  作者：Salil Putatunda、Srabasti Chakraborty、Swatilekha Ghosh、Pinki Nandi、Supriya Chakraborty、Parimal C. Sen、Arijit Chakraborty

  DOI：10.1016/j.ejmech.2012.04.043

  日期：2012.8

  A regioselective N1-alkylation of 3,4-dihydropyrimidin-2(1H)-ones using a very efficient mild base Cs2CO3 and alkyl halides at room temperature has been reported. The selectivity of this methodology is excellent and the yields of the alkylated products are very good. Furthermore inhibitory action of both the 3,4-dihydropyrimidin-2(1H)-ones and the N1-alkylated derivatives were tested on Ca2+-ATPase, which revealed that the parent compounds can act as Ca2+-ATPase inhibitors whereas the N1-alkylated derivatives are inefficient for this purpose. (C) 2012 Elsevier Masson SAS. All rights reserved.