187532-11-2

Basic information

• Product Name: Aziridine, 2-ethenyl-3-(1-methylethyl)-1-[(2,4,6-trimethylphenyl)sulfonyl]-, (2R,3S)-
• CAS NO: 187532-11-2
• Molecular Formula: C16H23NO2S
• Molecular Weight: 293.43
• Mol File: 187532-11-2.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Aziridine, 2-ethenyl-3-(1-methylethyl)-1-[(2,4,6-trimethylphenyl)sulfonyl]-, (2R,3S)-(CAS DataBase Reference)
• NIST Chemistry Reference: Aziridine, 2-ethenyl-3-(1-methylethyl)-1-[(2,4,6-trimethylphenyl)sulfonyl]-, (2R,3S)-(187532-11-2)
• EPA Substance Registry System: Aziridine, 2-ethenyl-3-(1-methylethyl)-1-[(2,4,6-trimethylphenyl)sulfonyl]-, (2R,3S)-(187532-11-2)

Safety Data

• Hazardous Substances Data: 187532-11-2(Hazardous Substances Data)

Upstream product

• 2026-48-4 (S)-valinol 
• 773-64-8 2-mesitylenesulphonyl chloride 
• 220306-75-2 N-((E)-(S)-4-Hydroxy-1-isopropyl-but-2-enyl)-2,4,6-trimethyl-benzenesulfonamide 
• 220306-69-4 (E)-(S)-5-Methyl-4-(2,4,6-trimethyl-benzenesulfonylamino)-hex-2-enoic acid methyl ester 
• 187532-09-8 (3S,4S)-5-methyl-4-[N-(2,4,6-trimethylbenzenesulfonyl)amino]-1-hexen-3-ol 
• 187532-10-1 (3R,4S)-5-methyl-4-[N-(2,4,6-trimethylbenzenesulfonyl)amino]-1-hexen-3-ol 
• 139192-50-0 (2S)-N-(2,4,6-trimethylbenzenesulfonyl)-2-amino-3-methyl-butanol 
• 247200-38-0 (4S,2Z)-5-Methyl-4-[(2,4,6-trimethylphenylsulfonyl)amino]hex-2-en-1-ol 
• 247200-33-5 Ethyl (4S,2Z)-5-methyl-4-[(2,4,6-trimethylphenylsulfonyl)amino]hex-2-enoate 
• 148838-43-1 N-((S)-1-Formyl-2-methyl-propyl)-2,4,6-trimethyl-benzenesulfonamide 
• 220306-83-2 Methanesulfonic acid (E)-(S)-5-methyl-4-(2,4,6-trimethyl-benzenesulfonylamino)-hex-2-enyl ester 
• 220306-79-6 Carbonic acid methyl ester (E)-(S)-5-methyl-4-(2,4,6-trimethyl-benzenesulfonylamino)-hex-2-enyl ester 
• 220652-42-6 (4S,2Z)-O-Methoxycarbonyl-5-methyl-4-[(2,4,6-trimethylphenylsulfonyl)amino]hex-2-en-1-ol 
• 187532-12-3 (2S,3S)-3-Isopropyl-N-(2,4,6-trimethylphenylsulfonyl)-2-vinylaziridine 

Downstream Products

• 477781-06-9 N-{(1S,2R)-2-[(S)-Hydroxy-(4-methoxy-phenyl)-methyl]-1-isopropyl-but-3-enyl}-2,4,6-trimethyl-benzenesulfonamide 
• 189291-18-7 (E)-3-[(2R,3S)-3-Isopropyl-1-(2,4,6-trimethyl-benzenesulfonyl)-aziridin-2-yl]-acrylic acid tert-butyl ester 
• 477781-25-2 N-[(1S,2R)-2-((S)-Hydroxy-phenyl-methyl)-1-isopropyl-but-3-enyl]-2,4,6-trimethyl-benzenesulfonamide 
• 477781-07-0 N-{(1S,2R)-2-[(S)-(4-Chloro-phenyl)-hydroxy-methyl]-1-isopropyl-but-3-enyl}-2,4,6-trimethyl-benzenesulfonamide 

Relevant articles and documents

Selective synthesis of cis-2-vinyl-3-alkylaziridines and 3-pyrrolines from common intermediates (Z)-4-N-arylsulfonylaminoalk-2-en-1-ols

A simple method for the synthesis of both cis-2-vinylaziridines and 3-pyrrolines from common intermediate (Z)-4-(N-arylsulfonyl)amino-4-alkylbut-2-en-1-ols, is described. Palladium(0)-catalyzed reactions of methyl carbonates of the N-protected (Z)-4-amino-4-alkylbut-2-en-1-ols yield predominantly cis-3-alkyl-2-vinylaziridines. Alternatively, upon exposure to sodium hydride, methanesulfonates derived from N-protected (Z)-4-amino-4-alkylbut-2-en-1-ols give exclusively the corresponding 3-pyrrolines in high yields. A synthesis of biologically important (S)-3,4-dehydroproline is also presented.

A 2,3-cis-selective synthesis of aziridines bearing a vinyl group from allyl methyl carbonates and allyl mesylates

A convenient method for the synthesis of synthetically useful chiral 2-vinylaziridines from natural α-amino acids is described. Satisfactory 2,3-cis-selectivities are obtained by exposure of methyl carbonates of various allylic alcohols bearing an N-protected amino group to a catalytic amount of tetrakis(triphenylphosphine)palladium(0), Pd(PPh3)4, in aprotic solvents such as THF. Base-promoted aziridination of mesylates of various N-protected amino allylic alcohols followed by Pd(PPh3)4 catalyzed isomerization for the 2,3-cis-selective synthesis of vinylaziridines is also presented.

An unusual thermodynamic preference of chiral N-arylsulfonyl cis-3-alkyl-2-vinylaziridines over their trans-isomers: Palladium(0)-catalysed equilibration reactions

Palladium (0)-catalysed reactions of N-alkylsulfonyl- or N-arylsulfonyl-3-alkyl-2-vinylaziridines reveal that 2,3-cis-isomers are more stable than the corresponding 2,3-trans-isomers in accord with ab initio calculations.