114066-89-6

Basic information

• Product Name: N(1),N(3)-diallylthymine
• Synonyms: N(1),N(3)-diallylthymine
• CAS NO: 114066-89-6
• Molecular Formula: C11H14N2O2
• Molecular Weight: 206.24106
• Mol File: 114066-89-6.mol

Chemical Properties

• Boiling Point: 293°Cat760mmHg
• Flash Point: 116.6°C
• Appearance: /
• Density: 1.078g/cm³
• Vapor Pressure: 0.00177mmHg at 25°C
• Refractive Index: 1.513
• CAS DataBase Reference: N(1),N(3)-diallylthymine(CAS DataBase Reference)
• NIST Chemistry Reference: N(1),N(3)-diallylthymine(114066-89-6)
• EPA Substance Registry System: N(1),N(3)-diallylthymine(114066-89-6)

Safety Data

• Hazardous Substances Data: 114066-89-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H14N2O2/c1-4-6-12-8-9(3)10(14)13(7-5-2)11(12)15/h4-5,8H,1-2,6-7H2,3H3

Upstream product

• 106-95-6 allyl bromide 
• 65-71-4 thymin 
• 591-87-7 Allyl acetate 
• 7288-28-0 2,4-bis(trimethylsiloxy)-5-methylpyrimidine 

Relevant articles and documents

Synthesis of silicon precursors of modified oligonucleotides

The synthesis of four silicon nucleoside analogues for use as modified antisense oligonucleotide precursors, is described.

Microwave-assisted N-allylation of uracil and thymine pyrimidine bases

This work presents a new synthetic approach to N(1)-allylation of pyrimidine nucleobases with allyl bromide. The increased efficiency of the proposed method is based on two specific elements: (a) the nucleoside N-deprotonation is carried out in a homogeneous system by using sodium methylsulfinyl- methylide in DMSO; (b) the allylation reaction is microwave-assisted. This method ensures high yields (87-88%) of the monoallylated products and short reaction time (1.5 h as compared to tens of hours for classical methods), and provides protection against side reactions. NMR analysis of the crude reaction mixture indicated a ratio of 6-8 : 1 between N(1)-allyl derivatives and N(1),N(3)-diallyl derivatives.

Regiochemistry and Stereochemistry in Pd(0)-Catalyzed Allylic Alkylation of Nucleoside Bases

Allylic alkylation of amino- and hydroxy-azaheterocycles, in particular nucleoside bases, has been effected using Pd(0)-catalysis.A method has been developed for the preparation of carbocyclic nucleoside analogs such as the antiviral agent Carbovir.The synthesis of an appropriately substituted cyclopentenyl acetate for this reaction is described.Carbocyclic nucleosides of thymine at N-1, of adenine at N-9 and guanine at N-9 are described.Regiochemistry and stereochemistry of the products and intermediates have been determined by NMR studies.The (trimethylsilyl)ethyl group has been found to be an excellent protecting group for the 6-OH group in guanine, and it is readily removed by fluoride ions.