5-氟-1-甲基嘧啶-2,4-二酮 | 155-16-8

• 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-氟-1-甲基嘧啶-2,4-二酮
• 英文名称: 1-methyl-5-fluorouracil
• 英文别名: 5-fluoro-1-methyluracil；5-fluoro-1-methyl-1H-pyrimidine-2,4-dione；1-Methyl-5-fluor-uracil；5-Fluor-1-methyl-uracil；1-Methyl-5-fluoruracil；5-fluoro-1-methylpyrimidine-2,4-dione
• CAS: 155-16-8
• 化学式: C₅H₅FN₂O₂
• mdl: MFCD20544774
• 分子量: 144.105
• InChiKey: PPCVYQHUOMISIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  49.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-氟-1-甲基嘧啶-2,4-二酮 在 二异丁基氢化铝 、 一水合肼 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 以76.8 kg的产率得到4-氟-1H-吡唑
  参考文献：
  名称：

  CN115974784

  摘要：

  公开号：
• 作为产物：
  描述：

  5-fluoro-1-methyl-2-methylsulfanylpyrimidin-4(1H)-one 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 120.0h， 以90%的产率得到5-氟-1-甲基嘧啶-2,4-二酮
  参考文献：
  名称：

  Effect of the Structure of 1- and 3-Methyl-5-fluoropyrimidin-4-ones on H-D Exchange in Position 6 under Conditions of Base Catalysis

  摘要：

  Hydrogen atom in position 6 of 5-fluoro-1-methylpyrimidin-4(1H)-one and its 2-methylsulfan-yl,2-methoxy and 2-butylamino derivatives is readily replaced by deuterium in 90% methanol-d(4) at similar to20epsilonC under conditions of base catalysis. The rate of H-D exchange decreases in the series H, SMe > OMe >> NHBu. Isomeric 5-fluoro-3methylpyrimidin-4-ones, as well as their 5-unsubstituted analogs, do not undergo H-D exchange. Ready deuterium exchange in 5-fluoro-1-methylpyrimidin-4-ones is explained by synergistic effect of the zwitterionic structure and 5-fluorine atom on the C-6-H acidity. The gain in energy due to this effect, expressed through the enthalpy of dissociation of the C-6-H bond, is similar to15 kcal/mol provided that effect of the medium is absent; the contribution of the 5-fluorine atom is 5.3-6.0 kcal/mol.

  DOI：

  10.1023/b:rujo.0000034917.31926.78

文献信息

• Application of the Benzyloxycarbonyloxymethyl Moiety to a Protective Group of 5-Fluorouracil. Selective Alkylation of Amide Nitrogen of the Uracil Ring
  作者：Toshio Nagase、Kanzo Seike、Kazuto Shiraishi、Yutaka Yamada、Shoichiro Ozaki

  DOI：10.1246/cl.1988.1381

  日期：1988.8.5

  Selective alkylation of 5-fluorouracil using the benzyloxycarbonyloxymethyl moiety as a protective group of amide nitrogen of the uracil ring is described. Protection, alkylation and deprotection were carried out in high yields.

  描述了使用苄氧羰基氧甲基部分作为尿嘧啶环的酰胺氮保护基团的 5-氟尿嘧啶的选择性烷基化。以高产率进行保护、烷基化和脱保护。
• The Photocycloaddition Reactions of Uridine and Related Compounds with 2,3-Dimethyl-2-butene.
  作者：Ichiro ISHIKAWA、Tsuneo ITOH、Hiroaki TAKAYANAGI、Jun-ichi OSHIMA、Norio KAWAHARA、Yoshihisa MIZUNO、Haruo OGURA

  DOI：10.1248/cpb.39.1922

  日期：——

  The photochemical reactions of uracil and 5-fluorouracil derivatives with simple alkenes have been investigated. Photocycloaddition of uracil or 5-fluorouracil derivatives and 2, 3-dimethyl-2-butene in acetone gave an enantiomeric mixture of cross cycloadducts (4, 7) in moderate yields. Under similar conditions, diastereomers of 4-substituted 7, 7, 8, 8-tetramethyl-cis-2, 4-diazabicyclo[4.2.0]octane-3, 5-dione nucleosides (14-17) were formed from uridine or 5-fluorouridine derivatives in good yields. The structures and stereochemistry of these cycloadducts of the nucleoside series were elucidated on the basis of the proton nuclear magnetic resonance spectra and X-ray crystallographic analysis.

  研究了尿嘧啶和 5-氟尿嘧啶衍生物与简单烯烃的光化学反应。尿嘧啶或5-氟尿嘧啶衍生物与2, 3-二甲基-2-丁烯在丙酮中进行光环加成，以中等产率得到交叉环加合物(4, 7)的对映体混合物。在相似的条件下，由尿苷或5形成4-取代的7,7,8,8-四甲基-顺-2,4-二氮杂双环[4.2.0]辛烷-3,5-二酮核苷(14-17)的非对映体。 -氟尿苷衍生物的收率良好。基于质子核磁共振谱和X射线晶体学分析，阐明了这些核苷系列环加合物的结构和立体化学。
• Visser, W. M. Gerard; Herder, E. Renella; Kanter, Frans J. J. de, Journal of the Chemical Society. Perkin transactions I, 1988, p. 1203 - 1208
  作者：Visser, W. M. Gerard、Herder, E. Renella、Kanter, Frans J. J. de、Herscheid D. M. Jacobus

  DOI：——

  日期：——
• Kuz'menko, I. I.; Bobkov, V. N.; Zvolinskaya, T. V., Journal of general chemistry of the USSR, 1989, vol. 59, # 8.1, p. 1557 - 1561
  作者：Kuz'menko, I. I.、Bobkov, V. N.、Zvolinskaya, T. V.

  DOI：——

  日期：——
• Effect of the Structure of 1- and 3-Methylpyrimidin-4-ones on the Rate of Nucleophilic Substitution of the 2-Methylsylfanyl Group
  作者：G. M. Kheifets、V. A. Gindin、T. A. Nikolova

  DOI：10.1023/b:rujo.0000034918.26019.44

  日期：2004.1

  Rate constants for substitution of the 2-methylsulfanyl group in 1- and 3-methyl-2-methylsulfanylpyrimidin-4-ones and their 5-fluoro analogs were measured in the reaction with butylamine, alkaline hydrolysis, and methanolysis. The rate of substitution in 1-methyl isomers having a zwitterionic structure is greater by a factor of similar to2 than the rate of substitution in 3-methyl isomers with conjugated double bonds in the ring. The presence of a fluorine atom in position 5 accelerates nucleophilic substitution in 1-methyl isomers, while 5-fluoro-3-methyl-2-methylsulfanylpyrimidin-4-ones react at a lower rate than their 5-unsubstituted analogs. According to the NMR data, the reactions involve formation of a tetrahedral intermediate. Anchimeric effect of the methyl group on N-1 hampers attack by basic reagent on the C-6 atom.