145198-85-2

Basic information

• Product Name: N-(p-Toluenesulfonyl)-5-vinyl-6-aza-2-oxacyclohexan-1-one
• Synonyms: N-(p-Toluenesulfonyl)-5-vinyl-6-aza-2-oxacyclohexan-1-one
• CAS NO: 145198-85-2
• Molecular Weight: 281.332
• Mol File: 145198-85-2.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: N-(p-Toluenesulfonyl)-5-vinyl-6-aza-2-oxacyclohexan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: N-(p-Toluenesulfonyl)-5-vinyl-6-aza-2-oxacyclohexan-1-one(145198-85-2)
• EPA Substance Registry System: N-(p-Toluenesulfonyl)-5-vinyl-6-aza-2-oxacyclohexan-1-one(145198-85-2)

Safety Data

• Hazardous Substances Data: 145198-85-2(Hazardous Substances Data)

Upstream product

• 155354-80-6 penta-3,4-dien-1-yl tosylcarbamate 
• 1201224-03-4 pent-4-enyl (N-p-toluenesulfonyl)carbamate 
• 5557-87-9 3,4-pentadiene-1-ol 
• 4083-64-1 Tosyl isocyanate 
• 821-09-0 n-Pent-4-enyl alcohol 
• 30332-99-1 penta-3,4-dienoic acid ethyl ester 
• 113495-34-4 3-vinyl-2,6-dioxacyclohexan-1-one 

Relevant articles and documents

Rhodium-Catalyzed Asymmetric Intramolecular Hydroamination of Allenes

The rhodium-catalyzed asymmetric intramolecular hydroamination of sulfonyl amides with terminal allenes is reported. It provides selective access to 5- and 6-membered N-heterocycles, scaffolds found in a large range of different bioactive compounds. Moreover, gram scale reactions, as well as the application of suitable product transformations to natural products and key intermediates thereof are demonstrated.

Striking AcOH acceleration in direct intramolecular allylie amination reactions

An experiment was conducted to demonstrate that a strong accelerating effect occurs in direct intramolecular allylic amination when the reaction is conducted in AcOH rather than in CHCl or THF. A round bottom flask under air was charged with N-tosylcarbamate 3a-j, Pd(OAc)2, bis-sulfoxide ligand LL, phenylbenzoquinone and AcOH. The reaction was allowed to stir at 45°C for 24 h. The reaction mixture was hydrolysed and extracted with AcOEt. The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. Cyclisation of 3a was repeated in CH2Cl 2 and in AcOH by using stoichiometric amounts of Pd(OAc) without benzoquinone. Stoichiometric tests and computational DFT analysis of the palladium reoxidation step provide an overview of the structural and energetic role of acetic acid in increasing the efficacy of the entire catalytic cycle.

Regio- and stereoselective synthesis of 1,3-hydroxyl amines via palladium-catalyzed carbonate-carbamate transformation with unique stereoselectivity: Synthesis of 3-amino-4-penten-1-ols

The transformation of cyclic carbonates 1 to cyclic carbamates 4 is achieved in the presence of aryl or sulfonyl isocyanate by the catalysis of Pd(0) in high yield and with high structural flexibility. The reaction shows unique stereoselectivity: 3,4-disubstituted carbonates 2, irrespective of the composition of their stereoisomers, provide trans-5 exclusively or predominantly over cis-5. Mixtures of cis- and trans-3,5-disubstituted carbonates 3 furnish either cis-6 or trans-6 in high selectivity depending on the reaction conditions (kinetic or thermodynamic control, respectively). 1H NMR and X-ray structure analyses of 5 and 6 indicate that the stereochemical outcome is governed by an A1,2-strain between N-sulfonyl and C5-vinyl substituents.