3-(3,4-dihydro-5-bromo-2,4-dioxo-(2H)pyrimidin-1-yl)propanoic acid methyl ester | 22384-59-4

• 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-(3,4-dihydro-5-bromo-2,4-dioxo-(2H)pyrimidin-1-yl)propanoic acid methyl ester
• 英文别名: 3-(5-bromo-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)propionic acid methyl ester；methyl 3-(5-bromo-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propanoate；3-(5-bromo-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-propionic acid methyl ester；β-(5-Brom-uracilyl-3)-propionsaeure-methylester；Methyl 5-bromo-3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinepropanoate；methyl 3-(5-bromo-2,4-dioxopyrimidin-1-yl)propanoate
• CAS: 22384-59-4
• 化学式: C₈H₉BrN₂O₄
• 分子量: 277.074
• InChiKey: BDACDWASFYJLKQ-UHFFFAOYSA-N

物化性质

• 熔点：
  158-160 °C(Solv: ethanol (64-17-5))
• 密度：
  1.666±0.06 g/cm3(Predicted)

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

• 作为反应物：
  描述：

  3-(3,4-dihydro-5-bromo-2,4-dioxo-(2H)pyrimidin-1-yl)propanoic acid methyl ester 在 盐酸 、 水 作用下， 反应 0.5h， 生成 3-(3,4-dihydro-5-bromo-2,4-dioxopyrimidin-1(2H)-yl)propanoic acid
  参考文献：
  名称：

  对称和不对称的 alpha,omega-核碱基酰胺共轭系统。

  摘要：

  我们介绍了几种新型对称和不对称 α、ω-核碱基单-和双-酰胺共轭系统的合成和选定的物理化学性质，这些系统包含脂肪族、芳香族或糖类键。合成的最后阶段涉及带有羧基的亚单元与胺亚单元的缩合。发现 4-(4,6-二甲氧基-1,3,5-三嗪-2-基)-4-甲基吗啉氯化物 (DMT-MM) 是一种特别有效的缩合剂。含有羧基的亚基通过尿嘧啶的N-1迈克尔加合物或6-氯嘌呤的N-9迈克尔加合物与丙烯酸甲酯的酸水解获得。使用的胺是脂肪族/芳香族二胺、腺嘌呤、5-取代的1-(ω-氨基烷基)尿嘧啶和5'-氨基-2',5'-二脱氧胸苷。标题化合物可用作抗原生动物剂。此外，超分子行为的初步显微镜 TEM 研究表明，具有双亲结构的目标分子能够形成高度有序的组件，主要是纳米纤维。

  DOI：

  10.3762/bjoc.6.34
• 作为产物：
  描述：

  5-溴尿嘧啶 、 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， 反应 24.08h， 以98%的产率得到3-(3,4-dihydro-5-bromo-2,4-dioxo-(2H)pyrimidin-1-yl)propanoic acid methyl ester
  参考文献：
  名称：

  N-1和N-3尿嘧啶加合物的区域选择性合成中的Michael与Michael逆反应

  摘要：

  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。

  DOI：

  10.1016/j.tet.2010.08.059

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。
• Novel Acyclic Amide-Conjugated Nucleosides and Their Analogues
  作者：Slawomir Boncel、Krzysztof Walczak

  DOI：10.1080/15257770902736467

  日期：2009.3.11

  An effective one-step synthesis of new amide-conjugated nucleosides and their analogues, in the presence of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) as the condensing agent, is presented. Substrate subunits carrying carboxylic group were obtained by acidic hydrolysis of Michael-type adducts of various 5-substituted uracil derivatives to methyl acrylate. Amine substrate was synthesized by reduction of 1-(2'-cyanoethyl)thymine with sodium borohydride in the presence of nickel (II) chloride as catalyst. Other applied amine substrates were 5'-amino-5'-deoxythymidine and 5-aminouracil.
• Promiscuous acylase-catalyzed aza-Michael additions of aromatic N-heterocycles in organic solvent
  作者：Chao Qian、Jian-Ming Xu、Qi Wu、De-Shui Lv、Xian-Fu Lin

  DOI：10.1016/j.tetlet.2007.06.164

  日期：2007.8

  A novel and efficient enzymatic promiscuous protocol for aza-Michael addition of aromatic N-heterocycles to alpha,beta-unsaturated compounds has been described. The reactions were catalyzed by promiscuous zinc-active-site acylase in organic solvent at 50 degrees C. The strategy works with a broad range of N-heterocycles to afford the corresponding Michael adduct with good yields in several hours (0.5-6 h). This catalytic promiscuity is the first example of metal-active-site enzyme-catalyzed aza-Michael addition for aromatic N-heterocycles. (c) 2007 Elsevier Ltd. All rights reserved.
• Symmetrical and unsymmetrical <i>α</i>,<i>ω</i>-nucleobase amide-conjugated systems
  作者：Sławomir Boncel、Maciej Mączka、Krzysztof K K Koziol、Radosław Motyka、Krzysztof Z Walczak

  DOI：10.3762/bjoc.6.34

  日期：——

  uracils or N-9 Michael adducts of 6-chloropurine with methyl acrylate. The amines used were aliphatic/aromatic diamines, adenine, 5-substituted 1-(omega-aminoalkyl)uracils and 5'-amino-2',5'-dideoxythymidine. The title compounds may find application as antiprotozoal agents. Moreover, preliminary microscopy TEM studies of supramolecular behaviour showed that target molecules with bolaamphiphilic structures

  我们介绍了几种新型对称和不对称 α、ω-核碱基单-和双-酰胺共轭系统的合成和选定的物理化学性质，这些系统包含脂肪族、芳香族或糖类键。合成的最后阶段涉及带有羧基的亚单元与胺亚单元的缩合。发现 4-(4,6-二甲氧基-1,3,5-三嗪-2-基)-4-甲基吗啉氯化物 (DMT-MM) 是一种特别有效的缩合剂。含有羧基的亚基通过尿嘧啶的N-1迈克尔加合物或6-氯嘌呤的N-9迈克尔加合物与丙烯酸甲酯的酸水解获得。使用的胺是脂肪族/芳香族二胺、腺嘌呤、5-取代的1-(ω-氨基烷基)尿嘧啶和5'-氨基-2',5'-二脱氧胸苷。标题化合物可用作抗原生动物剂。此外，超分子行为的初步显微镜 TEM 研究表明，具有双亲结构的目标分子能够形成高度有序的组件，主要是纳米纤维。
• 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。