6-(2-morpholinovinyl)-1,3-dimethyluracil | 303768-10-7

• 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: 6-(2-morpholinovinyl)-1,3-dimethyluracil
• 英文别名: 1,3-Dimethyl-6-(2-morpholin-4-ylethenyl)pyrimidine-2,4-dione
• CAS: 303768-10-7
• 化学式: C₁₂H₁₇N₃O₃
• 分子量: 251.285
• InChiKey: AMZQIQLSAXYFAC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.61
• 重原子数：
  18.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  56.47
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  6-(2-morpholinovinyl)-1,3-dimethyluracil 、 丙炔酸乙酯 在 indium(III) triflate 作用下， 以 neat (no solvent) 为溶剂， 反应 0.25h， 以89%的产率得到C₁₃H₁₄N₂O₄
  参考文献：
  名称：

  Indium-catalyzed microwave-accelerated pot economic C–C bond formation process towards the ‘dry-media’ synthesis of pyrimidine derivatives

  摘要：

  通过利用微波加速的C-C键形成过程，通过路易斯酸催化的Diels-Alder反应，从易得的尿嘧啶二烯和电子不足的乙炔羧酸酯中，可以高产率地构建取代嘧啶。

  DOI：

  10.1039/c4ra14434a

文献信息

• Efficient synthesis of dihydropyrido[4,3-d]pyrimidines by microwave-promoted three-component aza-Diels–Alder reaction
  作者：Manas M. Sarmah、Rupam Sarma、Dipak Prajapati、Wenhao Hu

  DOI：10.1016/j.tetlet.2012.11.018

  日期：2013.1

  A microwave-promoted solvent- and catalyst-free aza-Diels-Alder reaction is described. 6-[2-(dimethylamino)vinyl]-1,3-dimethyluracil reacts with aldehyde and amine inside a microwave reactor to produce dihydropyrido[4,3-d]pyrimidine derivatives in excellent yield and within a yew short time. (C) 2012 Elsevier Ltd. All rights reserved.
• An Efficient and Facile Synthesis of Iminoquinazolinedione Derivatives by Solid-State Diels-Alder Reaction under Catalyst-Free Conditions
  作者：Dipak Prajapati、Manas Sarmah、Debajyoti Bhuyan

  DOI：10.1055/s-0033-1339296

  日期：——

  A solvent-and catalyst-free Diels-Alder reaction with 6-(2-morpholinovinyl)-1,3-dimethyluracil, cinnamaldehyde, and an amine has been developed for the construction of iminoquinazoline-2,4-dione derivatives within a short reaction time. The method is clean, simple, and operation friendly.
• Microwave-Promoted Catalyst- and Solvent-Free Aza-Diels–Alder Reaction of Aldimines with 6-[2-(Dimethylamino)vinyl]-1,3-dimethyluracil
  作者：Rupam Sarma、Manas M. Sarmah、Dipak Prajapati

  DOI：10.1021/jo202346w

  日期：2012.2.17

  A microwave-promoted aza-Diels Alder reaction between 6[2-(dimethylamino)vinyl]-1,3-dimethyluracil and aldimines has been developed for the construction of dihydropyrido[4,3-d]pyrimidines. Urea is effectively employed as an environmentally benign source of ammonia in the absence of any catalyst or solvent. The key step in the reaction is in situ generation and trapping of the reactive aldimine formed from urea and aldehyde by the diene system of the uracil. The reaction is clean, and excellent yields are obtained in a matter of a few minutes.
• Indium-catalyzed microwave-accelerated pot economic C–C bond formation process towards the ‘dry-media’ synthesis of pyrimidine derivatives
  作者：Manas M. Sarmah、Debajyoti Bhuyan、Dipak Prajapati

  DOI：10.1039/c4ra14434a

  日期：——

  Substituted pyrimidines can be constructed in good yields via a microwave-accelerated C–C bond formation process through Lewis acid catalysed Diels–Alder reaction from easily available uracil diene and electron deficient acetylene carboxylate.

  通过利用微波加速的C-C键形成过程，通过路易斯酸催化的Diels-Alder反应，从易得的尿嘧啶二烯和电子不足的乙炔羧酸酯中，可以高产率地构建取代嘧啶。