5-羟基-1,3-二甲基嘧啶-2,4-二酮 | 20406-86-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 5-羟基-1,3-二甲基嘧啶-2,4-二酮
• 英文名称: 1,3-dimethyl-5-hydroxyuracil
• 英文别名: 5-hydroxy-1,3-dimethylpyrimidine-2,4(1H,3H)-dione；N,N'-dimethyl-5-hydroxyuracil；5-hydroxy-1,3-dimethyluracil；5-hydroxy-N,N-dimethyluracil；5-hydroxy-1,3-dimethyl-1H-pyrimidine-2,4-dione；5-Hydroxy-1,3-dimethyl-1H-pyrimidin-2,4-dion；5-hydroxy-1,3-dimethylpyrimidine-2,4-dione
• CAS: 20406-86-4
• 化学式: C₆H₈N₂O₃
• mdl: MFCD06658203
• 分子量: 156.141
• InChiKey: YUAQZUMPJSCOHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  60.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-羟基-1,3-二甲基嘧啶-2,4-二酮 在 palladium dichloride 三乙胺 、 三苯基膦 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 (E)-3-(1,3-dimethyl-2,4-dioxopyrimidin-5-yl)prop-2-enenitrile
  参考文献：
  名称：

  Palladium Catalyzed Coupling of 5-Hydroxyuracil Trifluoromethanesulfonates (Triflates) with Alkenes and Alkynes

  摘要：

  DOI：

  10.3987/r-1987-02-0355
• 作为产物：
  描述：

  5-甲氧基-1,3-二甲基嘧啶-2,4-二酮 在 三溴化硼 、 ammonium hydroxide 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到5-羟基-1,3-二甲基嘧啶-2,4-二酮
  参考文献：
  名称：

  Dehydrogenation, oxidative denitration and ring contraction of N,N-dimethyl-5-nitrouracil by a Bacillus nitroreductase Nfr-A1

  摘要：

  Nfr-A1, a Bacillus subtilis nitroreductase, catalyzes the nitroreduction of a large panel of aromatic and heterocyclic nitro compounds, except those belonging to nitrouracil class of molecules. Besides nitroreduction, Nfr-A1 exhibits a strong NADH oxidase activity in the presence of oxygen, leading to high concentration of H2O2 (up to 200 mu M). In the presence of (N,N)-dimethyl-5-nitrouracil 1 (dim-NU), Nfr-A1 achieves the reduction of dim-NU double bond to compounds 2 and 3 and in parallel the oxidation of dim-NU to the denitrated five membered derivatives 4 and 5. The reduction is catalyzed by the reduced Flavin Fl-(Red) and resembles those catalyzed by dihydropyrimidine clehydrogenases (DPD), during the catabolism of pyrimidines. The oxidative denitration is catalyzed in part by hydrogen peroxide generated through the NADH-oxidase activity, and certainly by the peroxyflavin intermediate Fl-(OOH) for the other part. The mechanisms of reaction were proposed according to experimental data and literature. These findings together with our previous results on the potential biological role of Nfr-A1, confirm the large spectrum of catalysis supported by this enzyme. The oxidative denitration is sporadically reported in literature and represents a safe and green alternative for the remediation of nitro-compounds. (C) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2011.11.014

文献信息

• Studies on the chemistry of pyrimidine derivatives with dimethyldioxirane: synthesis, cytotoxic effect and antiviral activity of new 5,6-oxiranyl-5,6-dihydro and 5-hydroxy-5,6-dihydro-6-substituted uracil derivatives and pyrimidine nucleosides
  作者：Raffaele Saladino、Roberta Bernini、Claudia Crestini、Enrico Mincione、Alberto Bergamini、Stefano Marini、Anna Teresa Palamara

  DOI：10.1016/0040-4020(95)00380-q

  日期：1995.7

  The oxidation of uracil derivatives and pyrimidine nucleosides performed in CH2Cl2 with dimethyldioxirane afforded new 5,6-oxiranyl-5,6-dihydro and cis-/trans-5,6-dihvdroxv-5,6-dihydro-derivatives. When the oxidations were performed in the presence of methanol as nucleophile cis- and trans- 5-hydroxy-6-methoxy-5,6-dihydro derivatives were obtained in acceptable yields. Cis- and trans-1,3- dimethyl

  用二甲基二环氧乙烷在CH 2 Cl 2中进行尿嘧啶衍生物和嘧啶核苷的氧化，得到新的5，6-环氧乙烷基-5，6-二氢和顺式/反式-5，6-二羟基己酮-5，6-二氢衍生物。当在甲醇的存在下以亲核试剂的形式进行氧化时，以可接受的产率获得了顺式和反式5-羟基-6-甲氧基-5,6-二氢衍生物。通过1,3-二甲基-5,6-环氧乙烷基-5,6-二氢的亲核开环获得顺式和反式1,3-二甲基-5-羟基-6-烷基氨基-5,6-二氢尿嘧啶纯化形式的尿嘧啶。有趣的是，一些新的标题产品显示出低的细胞毒性和针对DNA和RNA病毒的选择性抗病毒活性。特别是化合物17b显示出对仙台病毒的强而有选择性的抑制作用，对单纯疱疹1病毒的影响较小。化合物17b在高浓度时也能够轻微抑制HIV-1病毒，但是在这种情况下，观察到了细胞毒性作用。
• Oxidation of Nucleic Acid Related Compounds by the Peroxodisulfate Ion
  作者：Toshio Itahara、Takashi Yoshitake、Sunao Koga、Akihiro Nishino

  DOI：10.1246/bcsj.67.2257

  日期：1994.8

  peroxodisulfate ion in a phosphate buffer solution at pH 7.0 or water at 70—75 °C was investigated. The reaction of thymine and 5-methylcytosine nucleosides and nucleotides resulted in the oxidation of the 5-methyl groups. The oxidation products from 1,3-dimethyluracils and the time-course of the reaction of uracils led to two plausible reaction mechanisms for the oxidation of uracils.

  研究了在 pH 7.0 的磷酸盐缓冲溶液或 70-75 °C 的水中用过二硫酸根离子处理核酸碱基、核苷和核苷酸。胸腺嘧啶和 5-甲基胞嘧啶核苷和核苷酸的反应导致 5-甲基基团的氧化。1,3-二甲基尿嘧啶的氧化产物和尿嘧啶反应的时间进程导致了两种可能的尿嘧啶氧化反应机制。
• Novel Synthesis of Nine-Membered Oxa-Heterocycles by Pd(0)-Catalyzed Intramolecular Heck Reaction via Unusual 9-<i>endo-trig</i>-Mode Cyclization
  作者：K. Majumdar、B. Chattopadhyay

  DOI：10.1055/s-2008-1072510

  日期：——

  Syntheses of nine-membered oxa-heterocyclic compounds by the application of the intramolecular Heck reaction have been difficult to develop. Herein, we describe the synthesis of this class of compounds through the 9- ENDO- TRIG cyclization and 8- ENDO- TRIG cyclization, respectively - a rare mode of cyclization in the literature.

  应用分子内 Heck 反应合成九元氧杂杂环化合物一直很困难。在本文中，我们分别通过 9-ENDO-TRIG 环化和 8-ENDO-TRIG 环化来描述此类化合物的合成——这是文献中罕见的环化模式。
• The Directed ortho Metalation (DoM)–Cross-Coupling Connection: Synthesis of Polyfunctional Biaryls
  作者：Victor Snieckus、Claude Quesnelle

  DOI：10.1055/s-0037-1610273

  日期：2018.11

  cross-coupling reactions with aryl triflates for the synthesis of substituted biaryls is described. Both ortho-zinc and ortho-boron aryl directed metalation group (DMG = CON(i-Pr)2, OCONEt2, OMOM, NHBoc) substrates were evaluated. The superiority of the DoM–Negishi over the DoM–Suzuki–Miyaura reaction in operational convenience and mild reaction conditions is noted. Orthogonal Negishi and Suzuki–Miyaura with

  致力于斯科特·丹麦（Scott Denmark），他是有机化学领域中所有季节的专家。 发布时间作为的一部分奉献给斯科特E.丹麦在他65之际特别节日的生日。 抽象的 将合并的定向进行比较评价邻金属化（d ö M）-Suzuki -宫浦和d ö M-根岸与芳基三氟甲磺酸酯为取代的联芳基化合物的合成的交叉偶联反应进行说明。两个邻位-锌和邻-硼芳定向金属化基团（DMG = CON（我-Pr）2，OCONEt 2，OMOM，NHBoc基）基底进行了评价。D o M–Negishi优于D o注意到在操作方便性和温和的反应条件下，M–Suzuki–Miyaura反应。还报道了带有Neorishi和Suzuki-Miyaura的正交反应，并带有Corriu-Kumada反应合成了芳基衍生物。 将合并的定向进行比较评价邻金属化（d ö M）-Suzuki -宫浦和d ö M-根岸与芳基三氟甲磺酸酯为取代的联
• Regioselective synthesis of 1H,3H,6H[2]benzopyrano[4,3-d]pyrimidine-2,4-diones and 12H-benzopyrano[3,2-c][1]benzopyran-5-ones by radical cyclization
  作者：K.C Majumdar、P.K Basu、P.P Mukhopadhyay、S Sarkar、S.K Ghosh、P Biswas

  DOI：10.1016/s0040-4020(03)00182-0

  日期：2003.3

  5-Hydroxy uracils or 4-hydroxy[1]benzopyran-2-ones were refluxed with 2-bromobenzyl bromides in acetone in the presence of anhydrous potassium carbonate to afford a number of 5-(2′-bromobenzyloxy) pyrimidine-2,4-dione (80–92%) or 4-(2′-bromobenzyloxy) benzopyran-7-ones (70–82%) respectively. These were then refluxed with tri-n-butyltin chloride and sodium cyanoborohydride in the presence of a catalytic

  在无水碳酸钾存在下，将5-羟基尿嘧啶或4-羟基[1]苯并吡喃-2-酮与2-溴苄基溴在丙酮中回流，得到许多5-（2'-溴苄氧基）嘧啶-2,4 -二酮（80-92％）或4-（2'-溴苄氧基）苯并吡喃-7-酮（70-82％）。然后将这些与三回流Ñ 3-4小时中（AIBN）偶氮二异丁腈的催化量存在-butyltin氯和氰基硼氢化钠，得到1 ħ，3 ħ，6 ħ [2]苯并吡喃并[4,3- d ]嘧啶-2,4-二酮（75-85％）或12 H-苯并吡喃并[3,2- c ] [1]苯并吡喃-5-酮（70-85％）。