101194-49-4

Basic information

• Product Name: diethyl (1E,3E)-(1-methylsulfonyl-4-phenyl-1,3-butadienyl)phosphonate
• CAS NO: 101194-49-4
• Molecular Weight: 344.369
• Mol File: 101194-49-4.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: diethyl (1E,3E)-(1-methylsulfonyl-4-phenyl-1,3-butadienyl)phosphonate(CAS DataBase Reference)
• NIST Chemistry Reference: diethyl (1E,3E)-(1-methylsulfonyl-4-phenyl-1,3-butadienyl)phosphonate(101194-49-4)
• EPA Substance Registry System: diethyl (1E,3E)-(1-methylsulfonyl-4-phenyl-1,3-butadienyl)phosphonate(101194-49-4)

Safety Data

• Hazardous Substances Data: 101194-49-4(Hazardous Substances Data)

Upstream product

• 14371-10-9 (E)-3-phenylpropenal 
• 40137-11-9 diethyl methylsulfonylmethylphosphonate 

Downstream Products

• 101194-52-9 ((2E,4E)-1-Methanesulfonyl-5-phenyl-penta-2,4-dienyl)-phosphonic acid diethyl ester 
• 101194-57-4 (E)-diethyl 4-styryl-1H-pyrazol-3-ylphosphonate 
• 30313-22-5 1-(4'-methylphenyl)-5-phenyl-2,4-pentadiene-1-one 
• 86448-48-8 ((R)-1-Methanesulfonyl-4-phenyl-cyclopent-2-enyl)-phosphonic acid diethyl ester 
• 101219-50-5 (E)-3-diethoxyphosphinyl-3-methylsulfonyl-Δ¹-pyrazoline 

Relevant articles and documents

The Reaction of Butadienylphosphonates with a Oxosulfonium Ylide, Phosphonium Ylides, and Ketone Enolates

The condensation of diethyl (ethoxycarbonylmethyl)phosphonate (1a) with cinnamaldehyde in the presence of piperidine gave a 1:1 mixture of diethyl (1E,3E)- (2a) and (1Z,3E)-(1-ethoxycarbonyl-4-phenyl-1,3-butadienyl)phosphonates (2b) in 82percent yield, while a similar reaction using diethyl phosphonates (1c) exclusively gave diethyl (1E,3E)-phosphonates (4) in 78percent and 93percent yields, respectively.The reaction of the butadienylphosphonates 2-4 with dimethyloxosulfonium methylide (5) gave mixtures of (E)- and (Z)-(1-substituted 2-styrylcyclopropyl)phosphonates 7-9 in good yields.Similar treatment of the butadienylphosphonate 2 with phosphonium ylides 16a-c led to (3-substituted 1-ethoxycarbonyl-2-styrylcyclopropyl)phosphonates 17a-c in moderate yields.Reduction and oxidation of 7 were studied.The reaction of the phosphonates, 2 and 4, with ketone enolates and ketones resulted in the formation of unexpected olefins 22-24 and dienes 20a, b.The reaction mechanism is discussed.