100186-95-6

Basic information

• Product Name: 1,3-dimethylthymine epoxide
• Synonyms: 1,3-dimethylthymine epoxide
• CAS NO: 100186-95-6
• Molecular Formula: C7H10N2O3
• Molecular Weight: 170.1659
• Mol File: 100186-95-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 246.1°Cat760mmHg
• Flash Point: 102.7°C
• Appearance: /
• Density: 1.349g/cm³
• Vapor Pressure: 0.0276mmHg at 25°C
• Refractive Index: 1.539
• CAS DataBase Reference: 1,3-dimethylthymine epoxide(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-dimethylthymine epoxide(100186-95-6)
• EPA Substance Registry System: 1,3-dimethylthymine epoxide(100186-95-6)

Safety Data

• Hazardous Substances Data: 100186-95-6(Hazardous Substances Data)

Usage

General Description

1,3-dimethylthymine epoxide is a chemical compound that is a derivative of the nucleobase thymine. It is a reactive epoxide that can undergo nucleophilic attack and is known for its mutagenic and carcinogenic properties. 1,3-dimethylthymine epoxide has been studied for its potential applications in the field of medicinal chemistry and drug development, particularly in the context of understanding the mechanisms of DNA damage and repair. Due to its potential to cause genetic mutations and cancer, 1,3-dimethylthymine epoxide is considered a hazardous chemical and must be handled with caution in laboratory settings. Further research is ongoing to better understand the biological effects and potential uses of this compound.

InChI:InChI=1/C7H10N2O3/c1-7-4(10)8(2)6(11)9(3)5(7)12-7/h5H,1-3H3

Upstream product

• 90001-70-0 5-bomo-6-hydroxy-1,3,5-trimethyldihydropyrimidine-2,4-(1H,3H)-dione 
• 4401-71-2 1,3-dimethylthymine 
• 69596-94-7 dl-trans-5-bromo-6-hydroxy-1,3-dimethyl-5,6-dihydrothymine 

Downstream Products

• 110918-92-8 (S)-2-((4R,5S)-5-Hydroxy-1,3,5-trimethyl-2,6-dioxo-hexahydro-pyrimidin-4-ylamino)-3-phenyl-propionic acid benzyl ester 
• 110918-92-8 (S)-2-((4S,5S)-5-Hydroxy-1,3,5-trimethyl-2,6-dioxo-hexahydro-pyrimidin-4-ylamino)-3-phenyl-propionic acid benzyl ester 
• 100187-02-8 (S)-2-((4R,5S)-5-Hydroxy-1,3,5-trimethyl-2,6-dioxo-hexahydro-pyrimidin-4-ylamino)-3-phenyl-propionic acid ethyl ester 
• 100187-02-8 (S)-2-((4S,5S)-5-Hydroxy-1,3,5-trimethyl-2,6-dioxo-hexahydro-pyrimidin-4-ylamino)-3-phenyl-propionic acid ethyl ester 
• 100187-02-8 (S)-2-((4R,5R)-5-Hydroxy-1,3,5-trimethyl-2,6-dioxo-hexahydro-pyrimidin-4-ylamino)-3-phenyl-propionic acid ethyl ester 
• 100187-02-8 (S)-2-((4S,5R)-5-Hydroxy-1,3,5-trimethyl-2,6-dioxo-hexahydro-pyrimidin-4-ylamino)-3-phenyl-propionic acid ethyl ester 

Relevant articles and documents

Selective oxidation of uracil and adenine derivatives by the catalytic system MeReO3/H2O2 and MeReO3/urea hydrogen peroxide

Methyltrioxorhenium (MTO) is a useful and selective catalyst for the oxidation of uracil and purine derivatives using environmentally friendly hydrogen peroxide (H2O2, 30% water solution) or hydrogen peroxide/urea adduct (UHP) as oxygen atom donors. In particular, the MTO/UHP system constitutes a convenient combination to convert uracil derivatives into the biologically relevant 5,6-oxiranyl-5,6-dihydrouracils in good yields. Purine derivatives are selectively oxidized to the corresponding 1-oxides, the best yield being obtained in the presence of pyrazine-2-carboxylic acid (PCA). The oxidation of the plasmid pBG1 is also reported as the first example of double-strand DNA cleavage mediated by the catalytic system MTO/H2O2. (C) 2000 Elsevier Science Ltd.

The Reactivity of Thymine and Thymidine 5,6-Epoxides with Organometallic Reagents - A Route to Thymidine (6-4) Photoproduct Analogues

This report describes an efficient procedure for the generation and isolation of various thymine and thymidine 5,6-epoxides from the corresponding trans-5,6-bromohydrins by reaction with triethylamine. The quantitative isolation of the epoxides, accomplished by solvent precipitation of triethylamine hydrobromide, enabled their regiospecific ring-opening at C6 position by organometallic nucleophiles. The reaction was amenable to a broad range of alkyl, aryl, alkenyl, and alkynyl organomagnesium, -zinc, -aluminum, or -boron reagents, although the reactivity was strongly affected by the electronic effects of N3 protecting group. Additionally, the reaction featured excellent cis-diastereoselectivity providing access to C6-carbon-functionalized dihydrothymidine cis-alcohols, which are synthetic derivatives of UV-induced DNA lesions, namely, thymidine (6-4) photoproducts.

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

The oxidation of title substrates with dimethyldioxirane afforded 5,6-oxiranyl-5,6-dihydro and cis- / trans-5,6-disubstituted-5,6-dihydro-derivatives.