3-(5-chloro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)propionic acid methyl ester | 1256346-76-5

• 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: 3-(5-chloro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)propionic acid methyl ester
• 英文别名: methyl 3-(5-chloro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propanoate；methyl 3-(5-chloro-2,4-dioxopyrimidin-1-yl)propanoate
• CAS: 1256346-76-5
• 化学式: C₈H₉ClN₂O₄
• 分子量: 232.623
• InChiKey: PTKJZTVGBXPDDS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  75.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-氟脲嘧啶 、 丙烯酸甲酯（MA） 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 3-(5-chloro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)propionic acid methyl ester
  参考文献：
  名称：

  Facile Aza-Michael Additions of Uracil Derivatives to Acrylates

  摘要：

  以乙胺为催化剂，将 5-取代的尿嘧啶加到丙烯酸酯中，合成了 24 种 Aza-Michael 加合物，收率从中等到极好。许多加合物无需柱层析即可获得几乎定量的产率。该方法提供了一种以丙烯酸酯为受体合成 N-1 尿嘧啶加合物的有效途径。化合物的结构是通过 1H NMR、13C NMR、质谱和 X 射线晶体学分析确定的。尿嘧啶单元存在于 DNA 和相关天然产物中，具有广泛的生物活性。

  DOI：

  10.3184/174751912x13282923623804

文献信息

• Michael versus retro-Michael reaction in the regioselective synthesis of N-1 and N-3 uracil adducts
  作者：Sławomir Boncel、Maciej Mączka、Krzysztof Z. Walczak

  DOI：10.1016/j.tet.2010.08.059

  日期：2010.10

  controlling the temperature or reaction time in the base-catalysed Michael-type addition of 5-substituted uracil derivatives we were able to synthesise N-1 or N-3 uracil adducts using methyl acrylate and acrylonitrile as acceptors. The mechanism of this chemical inequivalence was established using 1H NMR spectroscopic studies. The investigations revealed that formation of the N-1 adduct was achievable

  通过控制5-取代的尿嘧啶衍生物在碱催化的迈克尔型加成反应中的温度或反应时间，我们能够使用丙烯酸甲酯和丙烯腈作为受体合成N-1或N-3尿嘧啶加合物。使用1 H NMR光谱研究确定了这种化学不等价的机理。研究表明，无论所用碱类（TEA，DBU）如何，在动力学控制条件下均可形成N-1加合物。反过来，N-3加合物的合成是从最初形成的N-1，N-3二加合物通过逆迈克尔反应进行的，该反应在升高的温度或延长的反应时间中起主导作用。
• Synthesis, Structural, and UV Studies of Two Uracil Derivatives, Methyl 3-(5-Fluoro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propanoate and Methyl 3-(5-Chloro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propanoate
  作者：Ting Yao、Jicheng Yi、Shuguang Zhou、Jing Xiong

  DOI：10.1007/s10870-013-0432-z

  日期：2013.7

  Two uracil derivatives of methyl 3-(5-fluoro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propanoate (1) and methyl 3-(5-chloro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propanoate (2) were synthesized and characterized by elementary analyses, MS, IR and NMR. The crystal structures of 1 and 2 were determined by means of X-ray diffraction. Compound 1 crystallized in the monoclinic P21/c space group with a = 7.4213(9), b = 5.8480(7), c = 23.248(3) Å, and β = 108.184(4)°. Compound 2 crystallized in the monoclinic P21/c space group with a = 12.5754(12), b = 4.9363(5), c = 16.5352(15) Å, and β = 97.455(3)°. The thermal stabilities of 1 and 2 were studied by DSC–TGA techniques. The UV spectra indicated that the two compounds interacted with DNA by electrostatic binding. The X-ray diffraction revealed that the N–H···O inter-molecular hydrogen bond in solid state of the two title compounds resulted in antiparallel β-sheet arrangement.

  合成了 3-(5-氟-2,4-二氧代-3,4-二氢嘧啶-1(2H)-基)丙酸甲酯(1)和 3-(5-氯-2,4-二氧代-3,4-二氢嘧啶-1(2H)-基)丙酸甲酯(2)的两种尿嘧啶衍生物，并通过基本分析、质谱、红外光谱和核磁共振对其进行了表征。通过 X 射线衍射确定了 1 和 2 的晶体结构。化合物 1 结晶于单斜 P21/c 空间群，a = 7.4213(9)，b = 5.8480(7)，c = 23.248(3) 埃，β = 108.184(4)°。化合物 2 结晶于单斜 P21/c 空间群，a = 12.5754(12)，b = 4.9363(5)，c = 16.5352(15) 埃，β = 97.455(3)°。通过 DSC-TGA 技术研究了 1 和 2 的热稳定性。紫外光谱显示这两种化合物通过静电结合与 DNA 发生作用。X 射线衍射显示，两种标题化合物在固态下的 N-H-O 分子间氢键导致了反平行的 β 片状排列。
• Facile Aza-Michael Additions of Uracil Derivatives to Acrylates
  作者：Shuguang Zhou、Mingxia Xu、Siyu Ye、Dashuai Li、Jing Xu、Pei Mao、Jing Xiong

  DOI：10.3184/174751912x13282923623804

  日期：2012.2

  24 Aza-Michael adducts were synthesised in moderate to excellent yields by the addition of 5-substituted uracils to acrylates with ethylamine as a catalyst. Many of the adducts were obtained in almost quantitive yield without column chromatography. The procedure provideded an efficient approach to the synthesis of N-1 uracil adducts using acrylates as acceptors. The structures of the compounds were determined by ¹H NMR, ¹³C NMR, mass spectra and X-ray crystallography analyses. The uracil unit is present in DNA and related natural products and has a broad spectrum of biological activity.

  以乙胺为催化剂，将 5-取代的尿嘧啶加到丙烯酸酯中，合成了 24 种 Aza-Michael 加合物，收率从中等到极好。许多加合物无需柱层析即可获得几乎定量的产率。该方法提供了一种以丙烯酸酯为受体合成 N-1 尿嘧啶加合物的有效途径。化合物的结构是通过 1H NMR、13C NMR、质谱和 X 射线晶体学分析确定的。尿嘧啶单元存在于 DNA 和相关天然产物中，具有广泛的生物活性。