87837-53-4

Basic information

• Product Name: Benzene, [(4-phenyl-1-butenyl)sulfonyl]-, (E)-
• CAS NO: 87837-53-4
• Molecular Formula: C16H16O2S
• Molecular Weight: 272.368
• Mol File: 87837-53-4.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: Benzene, [(4-phenyl-1-butenyl)sulfonyl]-, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzene, [(4-phenyl-1-butenyl)sulfonyl]-, (E)-(87837-53-4)
• EPA Substance Registry System: Benzene, [(4-phenyl-1-butenyl)sulfonyl]-, (E)-(87837-53-4)

Safety Data

• Hazardous Substances Data: 87837-53-4(Hazardous Substances Data)

Upstream product

• 38066-16-9 diethyl [(phenylthio)methyl]phosphonate 
• 126002-52-6 4-phenyl-1-phenylsulphonyl-1-(pyridine-2-thiyl)butane 
• 104-53-0 3-phenyl-propionaldehyde 
• 16003-66-0 ((dibromomethyl)sulfonyl)benzene 
• 768-56-9 4-Phenylbut-1-ene 
• 5535-48-8 PVS 
• 56069-39-7 diethyl phenylsulfonylmethylphosphonate 

Downstream Products

• 910823-70-0 (3R,4S,E)-4-(4-methoxybenzylamino)-1,6-diphenylhex-5-en-3-ol 
• 910823-69-7 (3S,4R,E)-4-(4-methoxybenzylamino)-1,6-diphenylhex-5-en-3-ol 
• 1363721-98-5 (2S)-2-((R)-fluoro{2-[(S)-p-tolylsulfinyl]phenyl}methyl)-4-phenylbutyl phenyl sulfone 
• 1363721-88-3 (2R)-2-((R)-fluoro{2-[(S)-p-tolylsulfinyl]phenyl}methyl)-4-phenylbutyl phenyl sulfone 
• 768-56-9 4-Phenylbut-1-ene 
• 88261-99-8 (Z)-trimethyl(4-phenylbut-1-en-1-yl)silane 
• 88261-98-7 (E)-trimethyl(4-phenylbut-1-en-1-yl)silane 
• 136091-86-6 1,2-dicyano-4-phenylbutane 
• 27066-35-9 (E)-1,4-diphenylbut-1-ene 
• 910823-65-3 (3S,4R,E)-4-(allylamino)-1,6-diphenylhex-5-en-3-ol 
• 910823-66-4 (3R,4S,E)-4-(allylamino)-1,6-diphenylhex-5-en-3-ol 
• 645-49-8 cis-stilben 
• 718615-41-9 (E)-4-phenyl-1-[tris(trimethylsilyl)silyl]-1-butene 
• 63909-24-0 2-methylene-4-phenylbutanenitrile 

Relevant articles and documents

Isomerisation of Vinyl Sulfones for the Stereoselective Synthesis of Vinyl Azides

Reported is the construction, and facile base-mediated conversation of ten differently substituted 3-azido E-vinyl sulfones (γ-azido-α,β-unsaturated sulfones) into their isomeric vinyl azide counterparts. The requisite 3-azido E-vinyl sulfones were prepared from 3-bromo E-vinyl sulfones, which in turn were accessed from allyl sulfones via a bromination-elimination sequence. In relation to this a one-pot azidation-isomerisation sequence was developed which enabled the direct formation of the vinyl azides from the corresponding 3-bromo E-vinyl sulfones. Similarly, a convenient one-pot Horner–Wadsworth–Emmons olefination-isomerisation approach was utilised in order to prepare some of the allylic sulfones used in this study. The vinyl azide forming process typically proceeded with high levels of Z-selectivity, although this was dependent on the vinyl sulfone substitution pattern. Thus, with either no substituent or a methyl group in the γ- or β-position, relative to the sulfone, good, to high levels of Z-selectivity (Z/E = 85:15 to ≥ 95:5) were obtained. However, incorporation of an α-sulfonyl methyl substituent led to an E-selective process (Z/E = 20:80). A non-bonding interaction between the azido group and the α-sulfonyl vinylic proton is proposed, which acts as a conformational control mechanism to help guide the stereochemical outcome.

Radical-mediated thiodesulfonylation of the vinyl sulfones: access to (α-fluoro)vinyl sulfides

Radical-mediated thiodesulfonylation of the vinyl and (α-fluoro)vinyl sulfones, derived from aldehydes and ketones, with aryl thiols in organic or aqueous medium provided access to vinyl and (α-fluoro)vinyl sulfides. The vinyl sulfides were formed predominantly with E stereochemistry independent of the stereochemistry of the starting vinyl sulfones.

Asymmetric synthesis of anti-1,2-amino alcohols via the borono-Mannich reaction: A formal synthesis of (-)-swainsonine

Chiral α-hydroxy aldehydes generated in situ by the ADH reaction of vinyl sulfones undergo a borono-Mannich reaction with β-styrenyl boronic acid and primary amines to give anti-1,2-amino alcohols in high enantiomeric purities (83-95% ee). This new method allows much more rapid access to these valuable chiral building blocks that has been used in a short formal synthesis (10 synthetic steps from 4-penten-1-ol) of (-)-swainsonine.