ethyl 2-(allylthio)-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyrimidine-5-carboxylate | 106720-52-9

• 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 2-(allylthio)-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyrimidine-5-carboxylate
• 英文别名: 1,4-dihydro-6-methyl-4-(3-nitrophenyl)-2-(2-propenylthio)-5-pyrimidinecarboxylic acid, ethyl ester；1,4-dihydro-6-methyl-4-(3-nitrophenyl)-2-(2-propenylthio)-5-pyrimidinecarboxylic acid,ethyl ester；Ethyl 6-methyl-4-(3-nitrophenyl)-2-prop-2-enylsulfanyl-1,4-dihydropyrimidine-5-carboxylate
• CAS: 106720-52-9
• 化学式: C₁₇H₁₉N₃O₄S
• 分子量: 361.422
• InChiKey: UKJJLZCOCZIGDB-UHFFFAOYSA-N

物化性质

• 沸点：
  481.3±55.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  122
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  ethyl 6-methyl-4-(3-nitrophenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-carboxylate 、 3-溴丙烯 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.33h， 以85%的产率得到ethyl 2-(allylthio)-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyrimidine-5-carboxylate
  参考文献：
  名称：

  Cs2CO3 介导的 3,4-二氢嘧啶-2(1H)-硫酮烷基化和酰化的简单选择性方法

  摘要：

  摘要 在 Cs2CO3（一种弱碱）存在下，合成了 3,4-二氢嘧啶-2(1H)-硫酮的烷基和酰基衍生物，收率非常好。该方法证明了在室温下使用酰氯作为 2-硫代-二氢嘧啶酮部分上的有效酰化剂时的选择性 S-烷基化。在几何优化过程的帮助下，对烷基化和酰化的不同选择性进行了可能的机械解释。

  DOI：

  10.1016/j.crci.2013.12.006

文献信息

• 2-substituted thio or oxy-4-aryl or
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04728652A1

  公开（公告）日：1988-03-01

  1,4-Dihydropyrimidines of the formula ##STR1## wherein X is sulfur or oxygen and R.sub.4 is aryl or heterocyclo and disclosed. These compounds are useful as cardiovacular agents, particularly anti-hypertensive agents, due to their vasodilator activity.

  该公式为##STR1##的1,4-二氢嘧啶化合物，其中X为硫或氧，R.sub.4为芳基或杂环基。这些化合物可用作心血管药物，特别是抗高血压药物，因为它们具有扩血管活性。
• Dihydropyrimidine calcium channel blockers: 2-heterosubstituted 4-aryl-1,4-dihydro-6-methyl-5-pyrimidinecarboxylic acid esters as potent mimics of dihydropyridines
  作者：Karnail S. Atwal、George C. Rovnyak、Joseph Schwartz、Suzanne Moreland、Anders Hedberg、Jack Z. Gougoutas、Mary F. Malley、David M. Floyd

  DOI：10.1021/jm00167a035

  日期：1990.5

  2-Heterosubstituted-4-aryl-1,4-dihydro-6-methyl-5-pyrimidinecar box ylic acid esters 8, which lack the potential CS symmetry of dihydropyridine calcium channel blockers, were prepared and evaluated for biological activity. Biological assays using potassium-depolarized rabbit aorta and radioligand binding techniques showed that some of these compounds are potent mimics of dihydropyridine calcium channel blockers. The combination of a branched ester (e.g. isopropyl, sec-butyl) and an alkylthio group (e.g. SMe) was found to be optimal for biological activity. When compared directly with similarly substituted 2-heteroalkyldihydropyridines 9, dihydropyrimidines 8 were found to be 30-fold less active. The solid-state structure of dihydropyrimidine analogue 8g shows that these compounds can adopt a molecular conformation which is similar to the reported conformation of dihydropyridine calcium channel blockers.
• A Cs2CO3-mediated simple and selective method for the alkylation and acylation of 3,4-dihydropyrimidin-2(1H)-thiones
  作者：Salil Putatunda、Arijit Chakraborty

  DOI：10.1016/j.crci.2013.12.006

  日期：2014.10

  excellent yields in the presence of Cs2CO3, a mild base. The method evidences a selective S-alkylation when using acyl chlorides as efficient acylating agents at room temperature on the 2-thioxo-dihydropyrimidone moiety. A possible mechanistic interpretation of the different selectivities in case of alkylation and acylation was done with the help of a geometry optimization process.

  摘要 在 Cs2CO3（一种弱碱）存在下，合成了 3,4-二氢嘧啶-2(1H)-硫酮的烷基和酰基衍生物，收率非常好。该方法证明了在室温下使用酰氯作为 2-硫代-二氢嘧啶酮部分上的有效酰化剂时的选择性 S-烷基化。在几何优化过程的帮助下，对烷基化和酰化的不同选择性进行了可能的机械解释。