6-[1-aza-2-(dimethylamino)prop-1-enyl]-1,3-dimethyl uracil

• 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-[1-aza-2-(dimethylamino)prop-1-enyl]-1,3-dimethyl uracil
• 英文别名: N'-(1,3-dimethyl-2,6-dioxopyrimidin-4-yl)-N,N-dimethylethanimidamide
• 化学式: C₁₀H₁₆N₄O₂
• 分子量: 224.263
• InChiKey: UZPGEDSDBCJCFG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  56.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-[1-aza-2-(dimethylamino)prop-1-enyl]-1,3-dimethyl uracil 在 sodium dithionite 、 sodium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 10.25h， 生成 6-amino-1,3,7-trimethyl-5-phenylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  A convenient synthesis of novel 5-aryl-pyrido[2,3-d]pyrimidines and screening of their preliminary antibacterial properties

  摘要：

  Exploiting the diene nature of 6[1-aza-2-(dimethylamino)prop-l-enyl]-1,3-dimethyluracil (2), novel 5-aryl-pyrido[2,3-d]pyrimidines (5a-h) have been synthesized. The reaction proceeds through a triene intermediate whose structure has been conclusively established by single crystal X-ray analysis. Role of water is intriguing as the reaction can be stopped at the intermediate stage. Synthesized compounds have been screened for possible antibacterial properties and results showed modest activity. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.01.128
• 作为产物：
  描述：

  1,1-二甲氧基-N,N-二甲基乙胺 、 1,3-二甲基-6-氨基脲嘧啶 反应 1.0h， 以90.62%的产率得到6-[1-aza-2-(dimethylamino)prop-1-enyl]-1,3-dimethyl uracil
  参考文献：
  名称：

  A convenient synthesis of novel 5-aryl-pyrido[2,3-d]pyrimidines and screening of their preliminary antibacterial properties

  摘要：

  Exploiting the diene nature of 6[1-aza-2-(dimethylamino)prop-l-enyl]-1,3-dimethyluracil (2), novel 5-aryl-pyrido[2,3-d]pyrimidines (5a-h) have been synthesized. The reaction proceeds through a triene intermediate whose structure has been conclusively established by single crystal X-ray analysis. Role of water is intriguing as the reaction can be stopped at the intermediate stage. Synthesized compounds have been screened for possible antibacterial properties and results showed modest activity. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2014.01.128

文献信息

• KI-VO(acac)₂-H₂O₂-AcOH, A New Iodinating System for Selective Iodination at C-5 Position of Activated Pyrimidinediones: A Combined Experimental and Density Functional Study
  作者：Lakhinath Saikia、Dhrubajyoti Talukdar、Ramesh C. Deka、Ashim J. Thakur

  DOI：10.1002/jhet.1575

  日期：2013.7

  KI‐VO(acac)2‐H2O2 in aqueous ethanolic medium with acetic acid as additive has been found to iodinate pyrimidinediones and aromatic amines. The methodology is mild, efficient, and environmentally benign. Density functional theory‐based reactivity parameters support the experimentally observed reactivity of pyrimidinedione derivatives.

  已发现在含水乙醇介质中以乙酸为添加剂的KI-VO（acac）2 -H 2 O 2可碘化嘧啶二酮和芳族胺。该方法是温和的，有效的且对环境无害的。基于密度泛函理论的反应性参数支持嘧啶二酮衍生物的实验观察到的反应性。