cis-1,3-dimethyl-5,6-dihydroxy-5,6-dihydro uracil | 64629-89-6

• 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: cis-1,3-dimethyl-5,6-dihydroxy-5,6-dihydro uracil
• 英文别名: cis-1,3-dimethyl-5,6-dihydroxy-5,6-dihydrouracil；cis-5,6-dihydro-5,6-dihydroxy-1,3-dimethyluracil；2,4(1H,3H)-Pyrimidinedione, dihydro-5,6-dihydroxy-1,3-dimethyl-, cis-；(5S,6R)-5,6-dihydroxy-1,3-dimethyl-1,3-diazinane-2,4-dione
• CAS: 64629-89-6
• 化学式: C₆H₁₀N₂O₄
• 分子量: 174.156
• InChiKey: VGEBBIXKWHUXNG-IUYQGCFVSA-N

物化性质

• 沸点：
  305.7±52.0 °C(Predicted)
• 密度：
  1.507±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  81.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1,3-二甲基脲嘧啶 在 urea-hydrogen peroxide 、 甲基三氧化铼(VII) 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以82%的产率得到1,3-dimethyl-5,6-oxyranyl-5,6-dihydro uracil
  参考文献：
  名称：

  MeReO 3 / H 2 O 2和MeReO 3 /尿素过氧化氢催化体系对尿嘧啶和腺嘌呤衍生物的选择性氧化

  摘要：

  甲基三（MTO）为尿嘧啶和嘌呤衍生物的使用环境友好的过氧化氢的氧化的有用的和选择性的催化剂（H 2 ö 2为氧原子供体，30％的水溶液）或过氧化氢/尿素加合（UHP）。尤其是，MTO / UHP系统构成了方便的组合，可以以高收率将尿嘧啶衍生物转化为生物学上相关的5,6-环氧乙烷基-5,6-二氢尿嘧啶。嘌呤衍生物被选择性氧化为相应的1-氧化物，在吡嗪-2-羧酸（PCA）存在下可获得最佳收率。也报道了质粒pBG1的氧化是由催化系统MTO / H 2 O 2介导的双链DNA切割的第一个实例。

  DOI：

  10.1016/s0040-4020(00)00974-1

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 uracil derivatives and pyrimidine nucleosides by dimethyldioxirane: A new and mild synthesis of 5,6-oxiranyl-5,6-dihydro and 5,6-dihydroxy-5,6-dihydro-derivatives.
  作者：Paolo Lupattelli、Raffaele Saladino、Enrico Mincione

  DOI：10.1016/s0040-4039(00)73740-3

  日期：1993.9

  The oxidation of title substrates with dimethyldioxirane afforded 5.6-oxiranyl-5,6-dihydro and cis-/trans-5,6-disubstituted-5,6-dihydro-derivatives.
• Fenton Chemistry of 1,3-Dimethyluracil
  作者：Jacob A. Theruvathu、Charuvila T. Aravindakumar、Roman Flyunt、Justus von Sonntag、Clemens von Sonntag

  DOI：10.1021/ja0109794

  日期：2001.9.1

  Hydroxyl radicals were generated in the Fenton reaction at pH 4 (Fe2+ + H2O2 - Fe3+ + (OH)-O-. + OH-, k approximate to 60 L mol(-1) s(-1)) and by pulse radiolysis (for the determination of kinetic data). They react rapidly with 1,3-dimethyluracil, 1,3-DMU (k = 6 x 10(9) L mol(-1) s(-1)). With H2O2 in excess and in the absence of O-2, 1,3-DMU consumption is 3.3 mol per mol Fe2+. 1,3-DMUglycol is the major product (2.95 mol per mol Fe2+). Dimers, prominent products of (OH)-O-.-induced reactions in the absence of Fe2+/Fe3+ (Al-Sheikhly, M.; von Sonntag, C. Z Naturforsch. 1983, 31b, 1622) are not formed. Addition of (OH)-O-. to the C(5)-C(6) double bond of 1,3-DMU yields reducing C(6)-yl 1 and oxidizing C(5)-yl radicals 2 in a 4:1 ratio. The yield of reducing radicals was determined with tetranitromethane by following the buildup of nitroform anion. Reaction of 1 with Fe3+ that builds up during the reaction or with H2O2 gives rise to a short-chain reaction that is terminated by the reaction of Fe2+ with 2, which re-forms 1,3-DMU. In the presence of O-2, 1.1 mol of 1,3-DMU and 0.6 mol of O-2 are consumed per mol Fe2+ while 0.16 mol of 1,3-DMU-glycol and 0.17 mol of organic hydroperoxides (besides further unidentified products) are formed. In the presence Of O-2, 1 and 2 are rapidly converted into the corresponding peroxyl radicals (k = 9.1 x 10(8) L mol(-1) s(-1)). Their bimolecular decay (2k = 1.1 x 10(9) L mol(-1) s(-1)) yields similar to 22% HO2./O-2(.-) in the course of fragmentation reactions involving the C(5)-C(6) bond. Reduction of Fe3+ by O-2(.-) leads to an increase in (OH)-O-. production that is partially offset by a consumption of Fe2+ in its reaction with the peroxyl radicals (formation of organic hydroperoxides, k approximate to 3 x 10(5) L mol(-1) s(-1); value derived by computer simulation).