5-(allylamino)-1,3-diethylpyrimidine-2,4(1H,3H)-dione | 1198278-86-2

• 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: 5-(allylamino)-1,3-diethylpyrimidine-2,4(1H,3H)-dione
• 英文别名: 1,3-Diethyl-5-(prop-2-enylamino)pyrimidine-2,4-dione；1,3-diethyl-5-(prop-2-enylamino)pyrimidine-2,4-dione
• CAS: 1198278-86-2
• 化学式: C₁₁H₁₇N₃O₂
• 分子量: 223.275
• InChiKey: FYHXLMVMOKOZOJ-UHFFFAOYSA-N

物化性质

• 沸点：
  324.4±52.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  52.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-(allylamino)-1,3-diethylpyrimidine-2,4(1H,3H)-dione 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 2.25h， 生成 2-(1,3-diethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)-2,3-dihydroisothiazole-1,1-dioxide
  参考文献：
  名称：

  Synthesis of Sultams by Ring-Closing Metathesis

  摘要：

  Synthesis of a series of five-membered sultams containing different hetero- or carbocycles were obtained in good to excellent yields by ring-closing metathesis (RCM) reaction. Many sultams were precipitated from the reaction mixture and they were easily separated by filtration without further purification.

  DOI：

  10.1055/s-0033-1340360
• 作为产物：
  描述：

  5-bromo-1,3-diethyluracil 、 丙烯胺 以 乙醇 为溶剂， 以82%的产率得到5-(allylamino)-1,3-diethylpyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  对于吡咯并[3,2-合成中的适宜方法d ]嘧啶（9- deazaxanthines）和呋喃并[3,2- d经由自由基环化]嘧啶

  摘要：

  通过氮杂-克莱森重排，然后进行自由基环化，已经获得了一种新的有效途径，用于以优异的产率合成取代的9-脱氮黄嘌呤。该方法也已经应用于呋喃并[3,2- d ]嘧啶的合成。

  DOI：

  10.1016/j.tet.2009.09.059

文献信息

• An expedient approach for the synthesis of pyrrolo[3,2-d]pyrimidines (9-deazaxanthines) and furo[3,2-d]pyrimidine via radical cyclization
  作者：K.C. Majumdar、Shovan Mondal

  DOI：10.1016/j.tet.2009.09.059

  日期：2009.11

  A new efficient route for the synthesis of substituted 9-deazaxanthines in excellent yields via aza-Claisen rearrangement followed by radical cyclization has been achieved. This methodology has also been applied to the synthesis of furo[3,2-d]pyrimidine.

  通过氮杂-克莱森重排，然后进行自由基环化，已经获得了一种新的有效途径，用于以优异的产率合成取代的9-脱氮黄嘌呤。该方法也已经应用于呋喃并[3,2- d ]嘧啶的合成。
• Concise Synthesis of Pyrimido-azocine Derivatives via Aza-Claisen Rearrangement and Intramolecular Heck Reaction
  作者：K. Majumdar、Shovan Mondal、Debankan Ghosh、Buddhadeb Chattopadhyay

  DOI：10.1055/s-0029-1219276

  日期：2010.4

  An expedient approach involving BF3˙OEt2-catalyzed aza-Claisen rearrangement and palladium-catalyzed intramolecular Heck reaction for the synthesis of pyrimidine-fused azocine derivatives is described. The mechanistic interpretation of the plausible mode of cyclization is also described. uracil - aza-Claisen rearrangement - azocine - Heck reaction

  描述了一种简便的方法，该方法涉及BF 3 = OEt 2催化的氮杂-克莱森重排和钯催化的分子内Heck反应，用于合成嘧啶融合的偶氮碱衍生物。还描述了合理的环化模式的机理解释。 尿嘧啶-氮杂-克莱森重排-偶氮电影-赫克反应
• Concise Access to Pyrimidine-Annulated Azepine and Azocine Derivatives by Ruthenium-Catalyzed Ring-Closing Metathesis
  作者：K. Majumdar、Shovan Mondal、Debankan Ghosh

  DOI：10.1055/s-0029-1219228

  日期：2010.4

  systems are commonly undertaken through cyclization and cycloaddition reactions, but the formation of seven- and eight-membered-ring systems are not as abundant. An efficient and high-yielding method for the synthesis of seven- and eight-membered-ring nitrogen-containing heterocycles by ring-closing metathesis is reported. uracil - azepine - azocine - ring-closing metathesis

  通常通过环化和环加成反应对五元和六元环系统进行合成，但是七元和八元环系统的形成并不那么丰富。报道了一种通过闭环易位合成七元和八元环含氮杂环的高效高产方法。 尿嘧啶-氮杂-偶氮辛-闭环复分解
• Synthesis of Sultams by Ring-Closing Metathesis
  作者：Shovan Mondal、Sudarshan Debnath

  DOI：10.1055/s-0033-1340360

  日期：——

  Synthesis of a series of five-membered sultams containing different hetero- or carbocycles were obtained in good to excellent yields by ring-closing metathesis (RCM) reaction. Many sultams were precipitated from the reaction mixture and they were easily separated by filtration without further purification.
• An expedient approach for the regioselective synthesis of novel 1,5,6,7-tetrahydro-2H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione derivatives via Fe (III)-mediated iodocyclization
  作者：Subhadeep Samanta、Shovan Mondal

  DOI：10.1016/j.tetlet.2022.154223

  日期：2022.12

  Novel pyrrolo[3,2-d]pyrimidine derivatives have been synthesized by an efficient and regioselective Fe (III)-mediated iodocyclization method starting from a commercially available uracil compound. Here, iron has a dual role in the iodocyclization process by acting as a Lewis acid which promotes the release of I+ cation from iodine by removing iodide ion, and also as an oxidant which again generates

  新型吡咯并 [3,2- d ] 嘧啶衍生物已通过有效且区域选择性的 Fe (III) 介导的碘环化方法从市售尿嘧啶化合物开始合成。在此，铁在碘环化过程中具有双重作用，既作为路易斯酸通过去除碘离子促进碘释放 I +阳离子，又作为氧化剂从碘离子再次生成碘参与催化反应循环。