1,3-dimethyl-5-(phenylseleninyl)pyrimidine-2,4(1H,3H)-dione | 154705-66-5

• 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: 1,3-dimethyl-5-(phenylseleninyl)pyrimidine-2,4(1H,3H)-dione
• 英文别名: 1,3-dimethyl-5-selenninylphenyluracil；1,3-Dimethyl-5-phenylseleninylpyrimidine-2,4-dione
• CAS: 154705-66-5
• 化学式: C₁₂H₁₂N₂O₃Se
• 分子量: 311.199
• InChiKey: KYHUSFOFLDZEGK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.38
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  57.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,3-dimethyl-5-(phenylseleninyl)pyrimidine-2,4(1H,3H)-dione 在 镍 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 15.5h， 生成 1,3,4-三甲基尿嘧啶
  参考文献：
  名称：

  Development of Reactions of 6- and 5-Substituted 1,3-Dimethyluracils with Dimethylsulfoxonium Methylide

  摘要：

  6-Chloro-1,3-dimethyluracil (1) reacts with dimethylsulfoxonium methylide (3, 2 equiv) to give sulfoxonium ylide 8 (51%). The structure of 8 is established spectroscopically and by its reactions with various electrophiles and electron-deficient olefins. Thus, 8 is converted by HCl to sulfoxonium chloride ?, which then yields the 6-(chloromethyl)uracil 17 by heating in acetonitrile. Ylide 8 undergoes deuterium exchange at the Ei-position, at its methine carbon, and into its methyl groups attached to sulfur. Reaction of 8 with benzoyl chloride gives the highly substituted ylide 19 or the nucleophilic substitution products 17 and 18 depending on reaction conditions. Treatment of 8 with electron-deficient olefins yields 6-cyclopropyluracils 20-31. Many of the cyclopropyluracils have been converted to trans-1-(1,3-dimethyluracilyl)-2-vinylcylopropanes and cycloheptenyluracils. Reactions of 5-substituted uracils 2 (Z = SOPh and SeOPh) with ylide 3 have been developed. 5-(Phenylsulfinyl)uracil 48 yields cyclothymine derivative 49; 5-phenylseleninyluracil 52 gives methylide 8 as the major product.

  DOI：

  10.1021/jo981906e
• 作为产物：
  描述：

  1,3-二甲基脲嘧啶 在 ammonium persulfate 、 magnesium monoperoxyphthalate hexahydrate 作用下， 以 乙醇 、 水 为溶剂， 反应 13.0h， 生成 1,3-dimethyl-5-(phenylseleninyl)pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Development of Reactions of 6- and 5-Substituted 1,3-Dimethyluracils with Dimethylsulfoxonium Methylide

  摘要：

  6-Chloro-1,3-dimethyluracil (1) reacts with dimethylsulfoxonium methylide (3, 2 equiv) to give sulfoxonium ylide 8 (51%). The structure of 8 is established spectroscopically and by its reactions with various electrophiles and electron-deficient olefins. Thus, 8 is converted by HCl to sulfoxonium chloride ?, which then yields the 6-(chloromethyl)uracil 17 by heating in acetonitrile. Ylide 8 undergoes deuterium exchange at the Ei-position, at its methine carbon, and into its methyl groups attached to sulfur. Reaction of 8 with benzoyl chloride gives the highly substituted ylide 19 or the nucleophilic substitution products 17 and 18 depending on reaction conditions. Treatment of 8 with electron-deficient olefins yields 6-cyclopropyluracils 20-31. Many of the cyclopropyluracils have been converted to trans-1-(1,3-dimethyluracilyl)-2-vinylcylopropanes and cycloheptenyluracils. Reactions of 5-substituted uracils 2 (Z = SOPh and SeOPh) with ylide 3 have been developed. 5-(Phenylsulfinyl)uracil 48 yields cyclothymine derivative 49; 5-phenylseleninyluracil 52 gives methylide 8 as the major product.

  DOI：

  10.1021/jo981906e

文献信息

• A NaI/H₂O₂-Mediated Sulfenylation and Selenylation of Unprotected Uracil and Its Derivatives
  作者：Xue-Dong Li、Yu-Ting Gao、Ying-Jie Sun、Xiao-Yang Jin、Dong Wang、Li Liu、Liang Cheng

  DOI：10.1021/acs.orglett.9b02183

  日期：2019.9.6

  efficient iodide-catalyzed/hydrogen peroxide mediated sulfenylation and selenylation of unprotected uracil and its derivatives with simple thiols and diselenides was established. This coupling tolerates a broad variety of functional groups to provide diverse 5-sulfur/selenium-substituted uracil derivatives in good to excellent yields (up to 93%).

  建立了有效的碘化物催化/过氧化氢介导的未保护的尿嘧啶及其衍生物与简单硫醇和二硒化物的亚磺酰化和硒基化反应。这种偶联耐受多种官能团，以良好至极佳的收率（高达93％）提供各种5-硫/硒取代的尿嘧啶衍生物。
• Development of Reactions of 6- and 5-Substituted 1,3-Dimethyluracils with Dimethylsulfoxonium Methylide
  作者：Peter Norris、Harold Shechter

  DOI：10.1021/jo981906e

  日期：1999.10.1

  6-Chloro-1,3-dimethyluracil (1) reacts with dimethylsulfoxonium methylide (3, 2 equiv) to give sulfoxonium ylide 8 (51%). The structure of 8 is established spectroscopically and by its reactions with various electrophiles and electron-deficient olefins. Thus, 8 is converted by HCl to sulfoxonium chloride ?, which then yields the 6-(chloromethyl)uracil 17 by heating in acetonitrile. Ylide 8 undergoes deuterium exchange at the Ei-position, at its methine carbon, and into its methyl groups attached to sulfur. Reaction of 8 with benzoyl chloride gives the highly substituted ylide 19 or the nucleophilic substitution products 17 and 18 depending on reaction conditions. Treatment of 8 with electron-deficient olefins yields 6-cyclopropyluracils 20-31. Many of the cyclopropyluracils have been converted to trans-1-(1,3-dimethyluracilyl)-2-vinylcylopropanes and cycloheptenyluracils. Reactions of 5-substituted uracils 2 (Z = SOPh and SeOPh) with ylide 3 have been developed. 5-(Phenylsulfinyl)uracil 48 yields cyclothymine derivative 49; 5-phenylseleninyluracil 52 gives methylide 8 as the major product.