3-(3,4-dihydro-5-nitro-2,4-dioxo-(2H)pyrimidin-1-yl)propanoic acid | 2950-86-9

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: 3-(3,4-dihydro-5-nitro-2,4-dioxo-(2H)pyrimidin-1-yl)propanoic acid
• 英文别名: 3-(5-nitro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)propanoic acid；3-(5-nitro-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-propionic acid；3,4-Dihydro-2,4-dioxo-5-nitro-1(2H)-pyrimidinpropionsaeure；3-(5-nitro-2,4-dioxopyrimidin-1-yl)propanoic acid
• CAS: 2950-86-9
• 化学式: C₇H₇N₃O₆
• 分子量: 229.149
• InChiKey: QMGQSEXXQZFJQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  133
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-(3-amino-propyl)-5-methyl-1H-pyrimidine-2,4-dione trifluoroacetate 、 3-(3,4-dihydro-5-nitro-2,4-dioxo-(2H)pyrimidin-1-yl)propanoic acid 在 N-甲基吗啉 、 4-(4,6-二甲氧基三嗪-2-基)-4-甲基吗啉盐酸盐 作用下， 以 四氢呋喃 为溶剂， 以30%的产率得到3-(3,4-dihydro-5-nitro-2,4-dioxopyrimidin-1(2H)-yl)-N-(3-(3,4-dihydro-5-methyl-2,4-dioxopyrimidin-1(2H)-yl)propyl)propanamide
  参考文献：
  名称：

  Novel Acyclic Amide-Conjugated Nucleosides and Their Analogues

  摘要：

  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.

  DOI：

  10.1080/15257770902736467
• 作为产物：
  描述：

  3-(3,4-dihydro-5-nitro-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-nitro-2,4-dioxo-(2H)pyrimidin-1-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

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.
• 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。