20245-84-5

Basic information

• Product Name: 1-vinylthymine
• Synonyms: 1-vinylthymine
• CAS NO: 20245-84-5
• Molecular Formula: C₇H₈N₂O₂
• Molecular Weight: 152
• Mol File: 20245-84-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-vinylthymine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-vinylthymine(20245-84-5)
• EPA Substance Registry System: 1-vinylthymine(20245-84-5)

Safety Data

• Hazardous Substances Data: 20245-84-5(Hazardous Substances Data)

Usage

Chemical origin

Derived from thymine, a nucleobase found in DNA.

Classification

Vinylated nucleoside.

Reactivity

Ability to form covalent adducts with DNA.

Mutagenic potential

Known for causing genetic mutations by forming crosslinks with DNA.

Role in carcinogenesis

May be an important factor in understanding the mechanisms of chemical carcinogenesis and the development of cancer.

Research application

Suggested as a tool to investigate the effects of its adducts on DNA structure and function.

Upstream product

• 22441-52-7 1-(2-chloroethyl)thymine 
• 196699-60-2 3-benzoyl-1-(2-chloroethyl)thymine 
• 53438-98-5 1-(2-bromoethyl)-5-methyl-1H-pyrimidine-2,4-dione 
• 106-93-4 ethylene dibromide 
• 65-71-4 thymin 
• 75-07-0 acetaldehyde 
• 4330-20-5 N-3-benzoylthymine 
• 4330-16-9 1,3-dibenzoyl-5-methylpyrimidine-2,4(1H,3H)-dione 
• 22441-51-6 N-1-(2-hydroxyethyl)thymine 
• 2768-02-7 (vinyl)trimethoxylsilane 
• 108-05-4 vinyl acetate 
• 74-86-2 acetylene 
• 7288-28-0 2,4-bis(trimethylsiloxy)-5-methylpyrimidine 
• 185960-21-8 5-Methyl-1-[3-(tetrahydro-pyran-2-yloxymethyl)-4,5-dihydro-isoxazol-5-yl]-1H-pyrimidine-2,4-dione 

Downstream Products

• 145215-37-8 1-(2-Benzyl-isoxazolidin-5-yl)-5-methyl-1H-pyrimidine-2,4-dione 
• 287195-06-6 1-{(3R,5S)-2-benzyl-3-[(1S)-2,2-dimethyl-1.3-dioxolan-4-yl]isoxazolidin-5-yl}thymine 
• 287195-02-2 1-{(3S,5R)-2-benzyl-3-[(4S)-2,2-dimethyl-1.3-dioxolan-4-yl]isoxazolidin-5-yl}thymine 
• 287195-03-3 1-{(3S,5S)-2-benzyl-3-[(4S)-2,2-dimethyl-1.3-dioxolan-4-yl]isoxazolidin-5-yl}thymine 
• 290293-17-3 1-{2-[6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-isoxazolidin-5-yl}-5-methyl-1H-pyrimidine-2,4-dione 
• 290293-15-1 1-{2-[6-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-isoxazolidin-5-yl}-5-methyl-1H-pyrimidine-2,4-dione 
• 256949-49-2 1-[(3R,5S)-2-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-3-ethoxycarbonyl-1,2-isoxazolidin-5-yl]-5-methyl-1H-pyrimidine-2,4(1H,3H)-dione 
• 256949-50-5 1-[(3R,5R)-2-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-3-ethoxycarbonyl-1,2-isoxazolidin-5-yl]-5-methyl-1H-pyrimidine-2,4(1H,3H)-dione 

Relevant articles and documents

Facile synthesis of N-(1-alkenyl) derivatives of 2,4-pyrimidinediones

N-(1-alkenyl) derivatives of 2,4-pyrimidinediones (6 - 9) were prepared in a one pot synthesis from aldehydes and the nucleobases using trimethylsilyl trifluoromethanesulfonate (TfOTMS) as coupling reagent. Presilylation of the above nucleobases, and N6-benzoyladenine, with excess N,O-bis(trimethylsilyl)acetamide (BSA) followed by addition of one mol eq. TfOTMS yielded the N-(1-trimethylsilyloxyalkyl) derivatives 1 - 5.

A simple preparation of N-vinyl derivatives of DNA nucleobases

1-Vinylpyrimidines and 9-vinylpurines have been prepared via selective alkylation of the heterocyclic ring with 1,2-dibromoethane (or 1,2- dibromopropanol) followed by dehydrobromination with sodium ethoxide in ethanol/DMF.

Heterocyclic nucleoside analogues by cycloaddition reactions of 1- vinylthymine with 1,3-dipoles

1,3-Dipolar cycloaddition of 1-vinylthymine to azides, nitrile oxides, nitrones and nitronates has been investigated as a route to heterocyclic nucleoside analogues in which the nucleoside ribose moiety has been replaced by an alternative heterocycle. Reaction of 1-vinylthymine with highly reactive nitrile oxides affords 1(isoxazolin-5-yl)thymine products in excellent yield at room temperature. The less reactive nitrone dipoles undergo cycloaddition to 1-vinylthymine at elevated temperature to afford 1- (isoxazolidin-5-yl)thymine cycloadducts in good-to-moderate yields, but show a tendency to eliminate thymine from the cycloaddition products over long reaction times. Azide cycloadditions to 1-vinylthymine proceed only under forcing conditions to which the fragile triazoline products are unstable.

SYNTHESIS OF N-VINYL COMPOUNDS BY REACTING CYLIC NH-COMPOUNDS WITH ACETYLENE IN PRESENCE OF HOMOGENOUS CATALYST

Process to produce N-vinyl compounds by homogeneous catalysis, wherein acetylene is reacted with a cyclic compound comprising a cyclic compound having at least one nitrogen as ring member, bearing a substitutable hydrogen residue (cyclic compound C), in a liquid phase in the presence of a ruthenium complex comprising at least one phosphine as ligand (RuCat).

Ruthenium-catalyzed synthesis of vinylamides at low acetylene pressure

The reaction of cyclic amides with acetylene under low pressure, using ruthenium-phosphine catalysts, afforded a broad variety ofN-vinylated amides including (azabicyclic) lactams, oxazolidinones, benzoisoxazolones, isoindolinones, quinoxalinones, oxazinanones, cyclic urea derivatives (imidazolidinones), nucleobases (thymine), amino acid anhydrides and thiazolidinone.

Direct Prebiotic Pathway to DNA Nucleosides

It is assumed that RNA played a key role in the origin of life, and the transition to more complex but more stable DNA for continuous information storage and replication requires the development of a ribonucleotide reductase to obtain the deoxyribonucleot

Nucleoside Analogues: Synthesis from Strained Rings

Nucleoside analogues are widely employed as bioactive compounds against cancer and viral infections. Consequently, it is important to develop efficient synthetic methods to access them with high efficiency and structural diversity. Herein, we present a full account of our work on the synthesis of nucleoside analogues via annulations of donor acceptor aminocyclopropanes and aminocyclobutanes. Thymine- and uracil-derived diester cyclopropanes were accessed from the corresponding nucleobases via vinylation and rhodium-catalyzed cyclopropanation, and were then used in (3+2) annulations with aldehydes, ketones and enol ethers. The obtained analogues could be transformed into important hydroxymethyl derivatives. Thymine and fluoro-uracil-derived diester cyclobutanes obtained from the nucleobases via vinylation and (2+2) cycloaddition could also be used in a (4+2) annulation with aldehydes. Finally, purine-derived diester cyclopropanes could be accessed using the condensation of nucleobases with chloromethyl ethylidene malonates, but annulation reactions with this class of substrates were not successful.

[4+2]-Annulations of aminocyclobutanes

The first [4 + 2]-annulation between aminocyclobutanes and aldehydes to access tetrahydropyranyl amines is reported. With phthalimido cyclobutane dicarboxylates and aromatic aldehydes, tetrahydropyrans were obtained in 53-92% yield and 3:1-17:1 dr using scandium triflate or iron trichloride as catalyst. The use of thymine-or fluorouracil-substituted cyclobutanes gave direct access to six-membered ring nucleoside analogues. Finally, the [4 + 2]-annulation between aminocyclobutanes and enol ethers led to the corresponding cyclohexylamines.

Synthesis of (Carbo)nucleoside analogues by [3+2] annulation of aminocyclopropanes

(Carbo)nucleoside derivatives constitute an important class of pharmaceuticals, yet there are only few convergent methods to access new analogues. Here, we report the first synthesis of thymine-, uracil-, and 5-fluorouracil-substituted diester donor-acceptor cyclopropanes and their use in the indium- and tin-catalyzed [3+2] annulations with aldehydes, ketones, and enol ethers. The obtained diester products could be easily decarboxylated and reduced to the corresponding alcohols. The method gives access to a broad range of new (carbo)nucleoside analogues in only four or five steps and will be highly useful for the synthesis of libraries of bioactive compounds.

Synthesis of aminocyclobutanes by iron-catalyzed [2+2] cycloaddition

Fab Four: An iron-catalyzed [2+2] cycloaddition furnishes aminocyclobutanes with a broad range of substituents in excellent yields and diastereoselectivities. The products can be obtained on a gram scale and can be further converted to β-peptide derivatives in a few steps. Furthermore, a [4+2] cycloaddition between an aminocyclobutane and an olefin leads to the corresponding cyclohexylamines. Copyright