406864
5-氟-1,3-二甲基尿嘧啶
99%
别名:
1,3-二甲基-5-氟尿嘧啶, 2,4-二羟基-1,3-二甲基-5-氟嘧啶
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关于此项目
经验公式（希尔记法）:
C6H7FN2O2
化学文摘社编号:
分子量:
158.13
PubChem Substance ID:
UNSPSC Code:
12352100
Beilstein/REAXYS Number:
880396
MDL number:
Assay:
99%
SMILES string
CN1C=C(F)C(=O)N(C)C1=O
InChI
1S/C6H7FN2O2/c1-8-3-4(7)5(10)9(2)6(8)11/h3H,1-2H3
InChI key
DDEWVRFHURYTHA-UHFFFAOYSA-N
assay
99%
mp
132-134 °C (lit.)
functional group
fluoro
General description
Oxidation of 5-fluoro-1,3-dimethyluracil (5-FDMU) with m-chloroperbenzoic acid has been described. It is reported as antineoplastic drug. On photoirradiation, 5-fluoro-1,3-dimethyluracil yields the trans-anti cyclobutane dimer and the cis-syn cyclobutane dimer. UV irradiation of 5-FDMU and naphthalene in a protic medium affords 5-(1-naphthyl)uracil, while in aprotic media it undergoes stereoselective 1,4-cycloaddition reaction to give a barrelene derivative. The thermochemical parameters of 5-FDMU has been determined. It reacts with substituted benzenes in the presence of trifluoroacetic acid to generate 5-aryl-1,3-dimethyluracils via photosubstitution.
Application
5-Fluoro-1,3-dimethyluracil may be used as starting material in the following processes:
- Regioselective synthesis of tetrahydronaphthocyclobuta[1,2-d]pyrimidinediones.
- To synthesize 5-bis(ethoxycarbonyl)methyl-1,3-dimethyluracil.
- To synthesize new highly conjugated propenylidene derivatives via aromatic Paterno-Buchi type cycloaddition with 1-methoxynaphthalene.
存储类别
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Hironao Sajiki et al.
Molecules (Basel, Switzerland), 17(6), 6519-6546 (2012-06-26)
The reaction of 5-halogenouracil and uridine derivatives 1 and 7 with active methylene compounds under basic conditions produced diverse and selective C-C bond formation products by virtue of the nature of the carbanions. Three different types of reactions such as
Synthesis of highly conjugated arylpropenylidene-1,3-diazin-2-ones via Paterno-Buchi reaction by photoreaction of 5-fluoro-1,3-dimethyluracil with 1-methoxynaphthalenes.
Seki KI, et al.
Chemistry Letters (Jpn), 37(8), 872-873 (2008)
Stereoselective synthesis of tetrahydronaphthocyclobuta [1, 2-d] pyrimidinediones from 5-fluoro-1, 3-dimethyluracil and naphthalenes.
Ohkura K, et al.
CRC Handbook of Thermoelectronics, 53(2), 258-259 (2005)
Acid-Catalyzed Photosubstitution of 5-Fluoro-1,3-Dimethyluracil with Substituted Benzenes.
Seki KI and Ohkura K.
Nucleosides and Nucleotides, 11(2-4), 521-527 (1992)
Kazue Ohkura et al.
Chemical & pharmaceutical bulletin, 53(2), 258-259 (2005-02-03)
Upon UV-irradiation in the presence of piperylene, 5-fluoro-1,3-dimethyluracil (5-FDMU) couples with naphthalenes having either an electron-withdrawing group or an electron-donating group by way of 1,2-cycloaddition via mode selectivity to give the corresponding naphthocyclobutapyrimidines regio- and stereo-selectively.
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