148408-52-0

Basic information

• Product Name: (E)-1-phenyl-penta-2,4-dien-1-one
• Synonyms: (E)-1-phenyl-penta-2,4-dien-1-one
• CAS NO: 148408-52-0
• Molecular Weight: 158.2
• Mol File: 148408-52-0.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (E)-1-phenyl-penta-2,4-dien-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-1-phenyl-penta-2,4-dien-1-one(148408-52-0)
• EPA Substance Registry System: (E)-1-phenyl-penta-2,4-dien-1-one(148408-52-0)

Safety Data

• Hazardous Substances Data: 148408-52-0(Hazardous Substances Data)

Upstream product

• 191099-41-9 1-phenyl-2-phenylseleno-4-penten-1-one 
• 98-86-2 acetophenone 
• 107-02-8 acrolein 
• 93-97-0 benzoic acid anhydride 
• 474758-24-2 (E)-1-dimethyl(phenyl)silylbuta-1,3-diene 
• 98-88-4 benzoyl chloride 
• 161562-80-7 (Z)-n-BuTe-CH=CH-CH=CH₂ 
• 18269-52-8 1-trimethylsilanyl-but-3-en-2-ol 
• 70-11-1 α-bromoacetophenone 

Relevant articles and documents

Carbon-carbon double bond formation between α-haloketones and aldehydes mediated by SnCl2/Na2SO3: Synthesis of (E) - α,β-unsaturated ketones

One-pot reactions of α-haloketones with aldehydes in the presence of excess SnCl2/Na2SO3 or SnCl2 alone in THF at reflux were found to afford (E) - α,β-unsaturated ketones in fair to good yields.

Carbon-carbon double bond formation between α-haloketones and aldehydes promoted by samarium triiodide

Reaction of α-haloketones with aldehydes in the presence of either SmI3 or Sm/I2 formed the carbon-carbon double bond to give α,β-unsaturated ketones in good to excellent yields under mild conditions. Samarium (III) enolates formed from the dehalogenation of α-haloketones by SmI3 were assumed to be the reaction intermediates.

Rhodium-catalyzed acylation of vinylsilanes with acid anhydrides

A catalytic acylation of vinylsilane with acid anhydride is accomplished by the use of [RhCl(CO)2]2, in which the transmetalation between vinylsilane and rhodium(I) carbonyl complex plays a key role. The application of this acylation reaction to (1-acyloxyvinyl)silanes provides synthetic methods for α-acyloxy enones, α-diketones, and their derivatives.

(E)- And (Z)-1-(Phenylsulfonyl)-4-(trimethylsilyl)-2-butenes: Synthetic Equivalents for the 1-(1,3-Butadienyl) Anion and the 1,1-(1,3-Butadienyl) Dianion

(E)- and (Z)-1-(phenylsulfonyl)-4-(trimethylsilyl)-2-butenes (7 and 8) are converted by n-BuLi to (E)- and (Z)-1-lithio-1-(phenylsulfonyl)-4-(trimethylsilyl)-2-butenes (15 and 16) with retention of initial stereochemistries. Reactions of 15 and 16 with electrophiles (protio and deuterio acids, primary, secondary, and benzyl halides, chloroformates, chlorothioformates, acid chlorides, epoxides, trialkylsilyl chlorides, and triethylgermanyl chloride) in THF or THF/HMPA give the corresponding (E)- and (Z)-1-(phenylsulfonyl)-1-substituted-4-(trimethylsilyl)-2-butenes (32) with stereochemical retention. That β,γ-unsaturated silyl sulfones 32 are formed instead of their α,β-unsaturated (conjugated) isomers are attributed to stabilizing multiple anionic and cationic hyperconjugation and to steric effects as in 29-31. Of importance in synthesis is that 32 are eliminated by TBAF at -20 to 0°C, thermally, or by column chromatography to (E)- (100 to > 93%) rather than (Z)-1-substituted-1,3-butadienes (38). Further, 32 undergo conversions by n-BuLi and various alkylating agents to (unconjugated) 1-(phenylsulfonyl)-1,1-disubstituted-4-(trimethylsilyl)-2-butenes (46) with retention of stereochemistry. Eliminations of 46 by fluoride ion, acid catalysis, or heat yield 1,1-disubstituted-1,3-butadienes (53). Silyl sulfones 7 and 8 are thus synthetic equivalents for the (E)-1-(1,3-butadienyl) anion (44) and the 1,1-(1,3-butadienyl) dianion (57). Silyl sulfones 7 and 8 also undergo efficient stereospecific intramolecular conversions by n-BuLi and α,ω-dihalides to 1,1-cycloalka-1-(phenylsulfonyl)-4-(trimethysilyl)-2-butenes (62 and 71) that are eliminated by fluoride ion, heat, or adsorption chromatography to 1,1-cycloalka-1,3-butadienes (72).