5-플루오로-1,3-다이메틸우라실

5-플루오로-1,3-다이메틸우라실 화학적 특성, 용도, 생산

• 용도

  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.

• Synthesis Reference(s)

  Tetrahedron, 46, p. 3093, 1990 DOI: 10.1016/S0040-4020(01)88400-3

• 일반 설명

  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.

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