ethyl 2-<(phenylthio)methyl>pyrimidine-5-carboxylate | 176240-57-6

• 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-<(phenylthio)methyl>pyrimidine-5-carboxylate
• 英文别名: Ethyl 2-(phenylsulfanylmethyl)pyrimidine-5-carboxylate
• CAS: 176240-57-6
• 化学式: C₁₄H₁₄N₂O₂S
• 分子量: 274.343
• InChiKey: WARFKOSTBBTOCK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  77.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 2-<(phenylthio)methyl>pyrimidine-5-carboxylate 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 ethyl 2-<1-acetoxy-2-(phenylthio)methyl>pyrimidine-5-carboxylate
  参考文献：
  名称：

  1,3-Diaza-1,3-butadienes. Synthesis and Conversion into Pyrimidines by [4π + 2π] Cycloaddition with Electron Deficient Acetylenes. Synthetic Utility of 2-(Trichloromethyl)pyrimidines¹

  摘要：

  Methods have been devised to generate 1H-1,3-diaza-1,3-butadienes bearing a leaving group at position-4 in latent, masked, and unprotected forms. A hallmark of these azadienes is that they undergo thermal [4 pi + 2 pi] cycloaddition reactions with electron deficient acetylenes to give adducts which are aromatized to pyrimidine derivatives under the reaction conditions. Thus, 1-(methoxycarbonyl)-3-acylamidines 17 on beating in solution are converted in situ into the 1,3-diaza-1,3-dienes 18 and/or 19 which react with dimethyl acetylenedicarboxylate (DMAD) to produce the pyrimidines 20. The 1-Boc-1,3-diaza-1,3-dienes 24 are masked forms of the LH-dienes inasmuch as they react with DMAD under relatively mild conditions to give the dihydropyrimidine adducts 25, which are easily detectable by H-1 NMR spectroscopy, and which aromatize to pyrimidines 26 at higher temperatures. The 4-methylthio compounds 31 and 33, and the 2-(trichloromethyl) compounds 37, are isolable, relatively stable, 1H-1,3-diaza-1,3-butadienes, These easily prepared compounds react with electron deficient acetylenes under mild conditions to provide the pyrimidines 20, 34, and 38, respectively, in fair to excellent yields. The 2-(trichloromethyl)pyrimidines 38 are very useful precursors of a wide variety of other 2-substituted pyrimidines 46-52.

  DOI：

  10.1021/jo952106w
• 作为产物：
  描述：

  苯硫酚 、 ethyl 2-(trichloromethyl)pyrimidine-5-carboxylate 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以98%的产率得到ethyl 2-<(phenylthio)methyl>pyrimidine-5-carboxylate
  参考文献：
  名称：

  Synthesis of Phenylthiomethyl Compounds from Trichloromethyl Derivatives

  摘要：

  本文介绍了一种在有噻吩酚存在的情况下，通过与噻吩酚钠反应将三氯甲基化合物转化为相应的苯硫甲基衍生物的新方法。这种转化在室温下进行，产率高，并已应用于多种三氯甲基化合物。

  DOI：

  10.1055/s-1999-3376

文献信息

• 1,3-Diaza-1,3-butadienes. Synthesis and Conversion into Pyrimidines by [4π + 2π] Cycloaddition with Electron Deficient Acetylenes. Synthetic Utility of 2-(Trichloromethyl)pyrimidines¹
  作者：Angel Guzmán、Moisés Romero、Francisco X. Talamás、Rene Villena、Robert Greenhouse、Joseph M. Muchowski

  DOI：10.1021/jo952106w

  日期：1996.1.1

  Methods have been devised to generate 1H-1,3-diaza-1,3-butadienes bearing a leaving group at position-4 in latent, masked, and unprotected forms. A hallmark of these azadienes is that they undergo thermal [4 pi + 2 pi] cycloaddition reactions with electron deficient acetylenes to give adducts which are aromatized to pyrimidine derivatives under the reaction conditions. Thus, 1-(methoxycarbonyl)-3-acylamidines 17 on beating in solution are converted in situ into the 1,3-diaza-1,3-dienes 18 and/or 19 which react with dimethyl acetylenedicarboxylate (DMAD) to produce the pyrimidines 20. The 1-Boc-1,3-diaza-1,3-dienes 24 are masked forms of the LH-dienes inasmuch as they react with DMAD under relatively mild conditions to give the dihydropyrimidine adducts 25, which are easily detectable by H-1 NMR spectroscopy, and which aromatize to pyrimidines 26 at higher temperatures. The 4-methylthio compounds 31 and 33, and the 2-(trichloromethyl) compounds 37, are isolable, relatively stable, 1H-1,3-diaza-1,3-butadienes, These easily prepared compounds react with electron deficient acetylenes under mild conditions to provide the pyrimidines 20, 34, and 38, respectively, in fair to excellent yields. The 2-(trichloromethyl)pyrimidines 38 are very useful precursors of a wide variety of other 2-substituted pyrimidines 46-52.
• Synthesis of Phenylthiomethyl Compounds from Trichloromethyl Derivatives
  作者：Moisés Romero-Ortega、Aydeé Fuentes、Carlos González、David Morales、Raymundo Cruz

  DOI：10.1055/s-1999-3376

  日期：1999.2

  A new method for the conversion of trichloromethyl compounds into the corresponding phenylthiomethyl derivatives by reaction with sodium thiophenolate in the presence of thiophenol is described. This transformation proceeds at room temperature in high yield and has been applied to a variety of trichloromethyl compounds.

  本文介绍了一种在有噻吩酚存在的情况下，通过与噻吩酚钠反应将三氯甲基化合物转化为相应的苯硫甲基衍生物的新方法。这种转化在室温下进行，产率高，并已应用于多种三氯甲基化合物。