54355-95-2

Upstream product

• 14371-10-9 (E)-3-phenylpropenal 
• 105-37-3 Ethyl propionate 
• 617-35-6 2-oxo-propionic acid ethyl ester 
• 56374-74-4 cinnamylidenetriphenylphosphorane 
• 21382-82-1 (carbethoxyethylidene)triphenylphosphorane 
• 103-82-2 phenylacetic acid 
• 535-11-5 Ethyl 2-bromopropionate 
• 2985-33-3 monoethyl methylmalonate 
• 54356-04-6 [(1-ethoxycarbonyl)ethylidene]triphenylphosphorane 
• 105-58-8 Diethyl carbonate 

Downstream Products

• 54355-96-3 (2E,4E)-2-methyl-5-phenylpenta-2,4-dien-1-ol 
• 111193-98-7 (3E,5E)-3-Methyl-6-phenyl-hexa-3,5-dienoic acid methyl ester 
• 143816-07-3 (2E,4E)-2-methyl-5-phenylpenta-2,4-dien-1-yl acetate 

Relevant academic research and scientific papers

Hydroperoxidations of Alkenes using Cobalt Picolinate Catalysts

Hydroperoxides were synthesized in one step from various alkenes using Co(pic)2as the catalyst with molecular oxygen and tetramethyldisiloxane (TMDSO). The hydration product could be obtained using a modified catalyst, Co(3-mepic)2, with molecular oxygen and phenylsilane. Formation of hydroperoxides occurred through a rapid Co-O bond metathesis of a peroxycobalt compound with isopropanol.

Synthesis of α,β-Disubstituted Acrylates via Galat Reaction

Galat reactions between aldehydes and substituted malonic acids half oxyester were found to be efficiently catalyzed by morpholine in refluxing toluene. This transformation allows the stereoselective synthesis of diverse α,β-disubstituted acrylates in moderate to good yields. This method constitutes an attractive alternative to existing methods in terms of scope and eco-compatibility.

Chromatography-free wittig reactions using a bifunctional polymeric reagent

The first example of a polystyrene bearing two distinct reagent groups has been prepared. This phosphine and amine functionalized material was used in one-pot Wittig reactions with an aldehyde and either an α-halo-ester, -ketone, or -amide. Due to the heterogeneous nature of the polymer, the desired alkene product of these reactions could be isolated in excellent yield in essentially pure form after only filtration and solvent removal.

Rasta resin-PPh3 and its use in chromatography-free wittig reactions

Rasta resin-PPh3, a new heterogeneous polystyrene-based phosphine, has been synthesized and used in one-pot Wittig olefination reactions of aldehydes. In these reactions an excess of rasta resin-PPh3 was used for the in situ generation of the phosphorane reactant and allowed for isolation of a high yield of very pure alkene product after only filtration and solvent removal. The excellent results obtained in this study are attributed to the flexible nature of the rasta resin structure, which makes it less dependant upon swelling than other heterogeneous polystyrene materials previously used to support phosphine reagents in Wittig reactions. Georg Thieme Verlag Stuttgart.

Reactivity of substituted and unsubstituted diphenylphosphonium diylides towards carbonic acids derivatives

In order to further delimit the scope of application of diphenylphosphonium diylides, their reactivity towards carbonic acid derivatives was investigated. Non-stabilized diylides react with ethyl carbonate to give new monoylide intermediates which lead, by in situ Wittig reaction with carbonyl compounds, to the synthesis of α,β-unsaturated esters or acids the double bond being di- or trisubstituted. The reaction proceeds in mild conditions and with high E stereoselectivity. Stabilized diylides are inactive towards carbonates but semi-stabilized diylides react with ethyl carbonate leading to the synthesis of non-functionalized alkenes instead of the α,β-unsaturated esters or acids.

Novel Synthesis of Phenol Derivatives by Palladium-Catalyzed Cyclocarbonylation of 2,4-Pentadienyl Acetates

Phenyl acetates were selectively obtained in good yields by cyclocarbonylation of 2,4-pentadienyl acetates in the presence of NEt3, Ac2O, and a catalytic amount of palladium complexes such as PdCl2(PPh3)2 at 120-140 deg C under 50 atm of CO.No five-membered ring products were observed.A platinum complex PtCl2(PPh3)2 was also effective as a catalyst.The reaction of 5-phenyl-2,4-pentadienyl bromide with M(CO)(PPh3)3 (M = Pd or Pt) under CO gave the corresponding 6-phenyl-3,5-hexadienoyl complexes in a high yield, which in turn afforded 2-acetoxybiphenyl in 41-51percent yield on heating to 160 deg C under 50 atm of CO in the presence of NEt3 and Ac2O.Similar 3,5-hexadienoyl complexes are proposed to be intermediates in the catalytic cyclocarbonylation of 2,4-pentadienyl acetates.On the other hand, PdCl2(PPh3)2-catalyzed carbonylation of o-(bromomethyl)(1-alkenyl)benzenes in the presence of NEt3 and Ac2O gave 2-naphthyl acetates in moderate yields, while the reaction in the absence of Ac2O gave five-membered ring products such as 2-indanones or a tricyclic lactone by incorporation of one or two CO, respectively.

Ultraviolet radiation absorbing compositions

Sunscreen compositions are described which contain certain 5-phenylpentadienoate esters which act as UV filters when incorporated in a carrier in amounts ranging from 0.1-50% by weight.

STEREOCONTROLLED SYNTHESES OF STROBILURIN A AND ITS (9E)-ISOMER

The (E,Z,E)-configuration (1) of the strobilurins has been confirmed by stereocontrolled synthesis.