6-[2-(dimethylamino)vinyl]-1,3-dimethyluracil | 120788-58-1

• 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-(dimethylamino)vinyl]-1,3-dimethyluracil
• 英文别名: 6-[2-(Dimethylamino)-vinyl]-1,3-dimethyluracil；6-[2-(dimethylamino)ethenyl]-1,3-dimethylpyrimidine-2,4-dione
• CAS: 120788-58-1
• 化学式: C₁₀H₁₅N₃O₂
• 分子量: 209.248
• InChiKey: HBNQQOKPVWVOMN-UHFFFAOYSA-N

物化性质

• 沸点：
  279.2±50.0 °C(Predicted)
• 密度：
  1.213±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  43.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-[2-(dimethylamino)vinyl]-1,3-dimethyluracil 、 富马酸二乙酯 以 甲苯 为溶剂， 反应 16.0h， 以32%的产率得到diethyl 1,2,3,4-tetrahydro-1,3-dimethyl-2,4-dioxo-5,6-quinazolinedicarboxylate
  参考文献：
  名称：

  Walsh, Eileen B.; Wamhoff, Heinrich, Chemische Berichte, 1989, vol. 122, p. 1673 - 1680

  摘要：

  DOI：
• 作为产物：
  描述：

  1,3,4-三甲基尿嘧啶 、 N,N-二甲基甲酰胺二甲基缩醛 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以69.4%的产率得到6-[2-(dimethylamino)vinyl]-1,3-dimethyluracil
  参考文献：
  名称：

  Walsh, Eileen B.; Wamhoff, Heinrich, Chemische Berichte, 1989, vol. 122, p. 1673 - 1680

  摘要：

  DOI：

文献信息

• 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。
• 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.
• Synthesis of Novel and Complex Tetrahydroquinazolinedione and Dihydro­pyrido[2,3-d]pyrimidine Derivatives via a One-Pot [4+2]-Cycloadddition Strategy
  作者：Dipak Prajapati、Manas Sarmah、Wenhao Hu

  DOI：10.1055/s-0032-1317792

  日期：——

  A mild and efficient protocol for the synthesis of various tetrahydroquinazolinedione and dihydropyrido[2,3-d]pyrimidine-2,4-dione templates from uracil derivatives utilizing a [4+2]-cycloaddition strategy in a one-pot reaction has been developed.
• 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.