41436-08-2

Upstream product

• 623-73-4 diazoacetic acid ethyl ester 
• 1896-62-4 (E)-benzalacetone 
• 39760-56-0 triethyl 3-methyl-4-phosphonocrotonate 
• 100-52-7 benzaldehyde 
• 888039-38-1 (2E)-ethyl 3-chloro-2-iodobut-2-enoate 
• 6783-05-7 trans-2-phenylvinylboronic acid 
• 100-42-5 styrene 
• 4341-76-8 Ethyl 2-butynoate 
• 104-55-2 3-phenyl-propenal 
• 122-57-6 1-Phenylbut-1-en-3-one 
• 1403959-51-2 ethyl 5-hydroxy-5-phenylpenta-2,3-dienoate 
• 75-16-1 methylmagnesium bromide 
• 129571-71-7 1-phenylpenta-1,4-dien-3-ol 
• 73291-51-7 1-phenyl-1,4-pentadien-3-one 

Downstream Products

• 71687-03-1 (2E,4E)-3-methyl-5-phenyl-2,4-pentadien-1-ol 
• 1452590-80-5 C₂₀H₂₉BO₄ 
• 53701-48-7 (2E,4E)-3-methyl-5-phenylpenta-2,4-dienal 

Relevant academic research and scientific papers

Sigmatropic rearrangement of allenic alcohols: Stereoselective synthesis of 1,3-diene-2-ol sulfonates

An efficient synthetic pathway to 1,3-diene-2-ol sulfonates involving the [3,3]-sigmatropic rearrangement of allenic alcohols with sulfonic acids under mild reaction conditions is described. These products can easily undergo reduction or transition-metal catalyzed cross-coupling reactions to yield a series of stereodefined multisubstituted 1,3-dienes.

Synthesis of Aromatic Retinoids and Curcuminoids and Evaluation of their Antiproliferative, Antiradical, and Anti-inflammatory Activities

Natural retinoids and curcuminoids are known for their broad spectrum of biological properties, such as antioxidant, anti-inflammatory, antitumor, and so forth. In this work, a convenient synthesis of aromatic retinoids and curcuminoids from vinyl or allyl ketones, and the corresponding alcohols, using olefin metathesis as a key reaction, was elaborated. The best yields and diastereoselectivities were obtained from allylic or homoallylic alcohols by employing the two-step cross-metathesis/oxidation procedure. The synthesized analogues were tested for their antiproliferative activity on human cancer cell lines of various origin (leukemia CEM, adenocarcinoma MCF7, cervical carcinoma HeLa) as well as for their antioxidant and anti-inflammatory activity in vitro. All examined derivatives exhibited strong anti-inflammatory activity in vitro without affecting cell viability. They also showed strong cytotoxicity against leukemia cell line CEM, except for 18 and 35. The antioxidant activity of the tested compounds was rather weak.

A newly-designed PE-supported arsine for efficient and practical catalytic Wittig olefination

A newly designed PE-supported arsine has been developed as an excellent catalyst for catalytic Wittig-type olefination. Simple ketones, in particular inactive ketones prove to be suitable substrates for the first time. This reaction provides an easy access to di-, tri-, and tetra-substituted olefins in high yield.

A cross-metathesis approach to the synthesis of new etretinate type retinoids, ethyl retinoate and its 9Z-isomer

Two aromatic retinoids were synthesized from styrene derivatives using a novel strategy with a cross-metathesis reaction as a key step. The biological activity of the new etretinate analogues was tested. Cross-metathesis reactions were also employed for the preparation of ethyl retinoate and its 9Z-isomer via the C15 + C5 route.

Cobalt-catalyzed regio- and stereoselective intermolecular enyne coupling: An efficient route to 1,3-diene derivatives

The reaction of alkynes with vinyl arenes or vinyl trimethyl silane in the presence of a cobalt(II) complex, Zn and ZnI2 in CH 2Cl2 at rt to 50 °C provides 1,3-dienes in good to excellent yields. The Royal Society of Chemistry 2010.

Rhodium-catalyzed regio- and stereoselective codimerization of alkenes and electron-deficient internal alkynes leading to 1,3-dienes

(Chemical Equation Presented) A cationic rhodium(I)/H8-BINAP complex catalyzes codimerization of alkenes bearing no r-hydrogen and electron-deficient internal alkynes, leading to 1,3-dienes in good yields with moderate to excellent regio- and stereoselectivity. The same complex also catalyzes codimerization of an acrylate and phenyl-substituted electron-rich internal alkynes, leading to 1,3-dienes.

Single-isomer trisubstituted olefins from a novel reaction of (E)-βchloro-α-iodo-α,β-unsaturated esters and amides

(Chemical Equation Presented) (E)-β-Chloro-α-iodo-α, β-unsaturated esters are converted to single isomer trisubstituted olefins bearing three different carbon substituents by cross-coupling under reflux. Mechanistic investigations suggest that this process transfers a hydrogen from the boronic acid to the α-position of the substrate and then introduces an aryl group to the β-position of the intermediate template while replacing chloride. The reaction is highly stereoselective, showing preference for the E-isomer. The process proceeds through (E)-β-chloro-α-aryl-α, β-unsaturated esters that are transformed efficiently into the corresponding E-products through stereoselective Suzuki-type reactions giving single isomers. The observed stereo-chemistry is apparently enabled by the intermediacy of a palladium allenoate. The reaction involves a catalytic cycle in which PdII is reduced to Pd0 through the formation of biaryl-coupled products.

Ruthenium-catalyzed tandem cross-metathesis/wittig olefination: Generation of conjugated dienoic esters from terminal olefins

In the presence of ruthenium-based olefin metathesis catalysts and triphenylphosphine, α,β-unsaturated aldehydes can be olefinated with diazoacetates. This ruthenium-catalyzed transformation has been employed in tandem with olefin cross-metathesis to convert terminal olefins into 1,3-dienoic esters in a single operation.

Photocurrents of solar cells sensitized by aggregate-forming polyenes: Enhancement due to suppression of singlet-triplet annihilation by lowering of dye concentration or light intensity

Titania-based Gr?tzel-type solar cells were fabricated by the use of polyene dyes with various transition dipole moments. In the dye having the largest transition dipole among the samples, an aggregate was readily formed through dispersive interaction, an

Acid-promoted olefination of ketones by an iron(III) porphyrin complex

(Matrix presented) The acid-promoted olefination of unactivated ketones with diazo reagents in the presence of triphenylphosphine can be catalyzed by the commercially available iron(III) porphyrin complex Fe(TPP)Cl. The reactions were effectively carried out under mild conditions in a one-pot fashion with the use of a stoichiometric diazo reagents and substoichiometric benzoic acid. Examples include aromatic, aliphatic, cyclic, and unsaturated ketones with ethyl diazoacetate or tert-butyl diazoacetate.