20414-94-2

Upstream product

• 20414-93-1 E-methyl-2-phenyl-5-pentadien-2,4-oate de methyle 
• 93440-96-1 (3E,5E)-3-Methyl-2-oxo-6-phenyl-3,5-hexadiensaeure (Kaliumsalz) 
• 344882-77-5 (E)-2-Methyl-1,1-bis-methylsulfanyl-5-phenyl-penta-1,4-dien-3-ol 
• 56427-10-2 5,5-Dichlor-4-methyl-1-phenyl-2,4-pentadien-1-ol 
• 104-55-2 3-phenyl-propenal 
• 103-26-4 methyl cinnamate 
• 100-52-7 benzaldehyde 
• 104-54-1 3-Phenylpropenol 
• 1367876-33-2 [(2Z,4E)-2-methoxycarbonyl-5-phenyl-2,4-pentadienyl]triphenylphosphonium bromide 
• 918155-94-9 methyl (2Z,4E)-2-(bromomethyl)-5-phenylpenta-2,4-dienoate 
• 1039704-01-2 ethyl (2E,4E)-5-phenyl-2-[(trimethylsilyl)methyl]penta-2,4-dienoate 
• 1039703-91-7 ethyl (2Z,4E)-5-phenyl-2-[(trimethylsilyl)methyl]penta-2,4-dienoate 
• 89812-55-5 (E)-2-Methyl-1,1-bis-methylsulfanyl-5-phenyl-penta-1,4-dien-3-one 
• 14371-10-9 (E)-3-phenylpropenal 

Downstream Products

• 73408-03-4 (E)-(S)-2-Methyl-5-phenyl-pent-4-enoic acid 
• 171483-81-1 (E)-(2R)-5-Phenyl-2-methyl-4-pentenoic acid 
• 406725-24-4 (2E,4E)-6-(2-Methyl-5-phenylpenta-2,4-dienoylamino)hexanoic acid methyl ester 

Relevant academic research and scientific papers

Highly Regio- A nd Enantioselective Hydrogenation of Conjugated α-Substituted Dienoic Acids

Highly regio- A nd enantioselective hydrogenation of conjugated α-substituted dienoic acids was realized for the first time using Trifer-Rh complex, providing a straightforward method for the synthesis of chiral α-substituted ?,?′-unsaturated acids. DFT calculations revealed N+H-O hydrogen bonding interaction is formed to stabilize the transition state and the coordination of 4,5-double bond to Rh(III) center would facilitate the reductive elimination process. This hydrogenation provided a gram-scale synthesis of the precursor of sacubitril.

Microwave-assisted synthesis of the (E)-α-methylalkenoate framework from multifunctionalized allylic phosphonium salts

A convenient and general microwave-assisted method for the synthesis of stereochemically defined α-methylalkenoic acids and esters from allylic phosphonium salts in a basic aqueous medium is described. A selective preparation of acids or esters was dependent on the base (NaOH or NaHCO 3) employed in the reaction and could be achieved with good to excellent yields under mild conditions in the absence of hydrides and reducing agents.

Correlation of hydrolysis and desilylation of 2-[(trimethylsilyl)methyl] acrylate derivatives in aqueous alkali solutions

Hydrolysis and desilylation reaction of 2-[(trimethylsilyl)methyl]acrylate (=2-[(trimethylsilyl)methyl] prop-2-enoate) derivatives were studied to evaluate the effect of the presence/absence of a further conjugating substituent (Schemes 3 and 4 and Tables 1 and 2). The substrates having a nonconjugating substituent at the acrylate moiety were stable to dilute alkali conditions, and afforded simple hydrolysis products under concentrated alkali conditions. In contrast, both hydrolysis and desilylation occurred from the substrates bearing conjugated substituents at the acrylate skeleton. The difference in reactivity can be explained in terms of the stabilization of the intermediate anion.

An efficient DABCO-catalyzed Ireland-Claisen rearrangement of allylic acrylates

A novel DABCO-catalyzed Ireland-Claisen [3,3]-rearrangement of allylic acrylates to give α-methylene-γ,δ-unsaturated carboxylic acids in the presence of an excess of TMSCl and DBU in refluxing acetonitrile was developed. The protocol provides an easy entry to α-methylene-γ, δ-unsaturated carboxylic acids from allylic alcohols in good yields. Georg Thieme Verlag Stuttgart.

Stereoselective synthesis of (E)-trisubstituted α,β-unsaturated amides and acids

Potassium alkoxides of N-acyl-oxazolidin-2-one-syn-aldols undergo stereoselective elimination reactions to afford a range of trisubstituted (E)-αβ-unsaturated amides in >95% de, that may be subsequently converted into their corresponding (E)-αβ-unsaturated acids or (E)-αβ-unsaturated oxazolines in good yield. syn-Aldols derived from αβ-unsaturated aldehydes gave their corresponding trisubstituted (E)-αβ-unsaturated-amides with poorer levels of diastereocontrol, whilst there was a similar loss in (E)-selectivity during elimination of syn-aldols derived from chiral aldehydes. These elimination reactions proceed via rearrangement of the potassium alkoxide of the syn-aldol to a 1,3-oxazinane-2,4-dione enolate intermediate that subsequently eliminates carbon dioxide to afford a trisubstituted (E)-αβ-unsaturated amide. The (E)-selectivity observed during the ElcB-type elimination step has been rationalised using a simple conformational model that employs a chair-like transition state to explain the observed stereocontrol. The Royal Society of Chemistry 2005.

Utility of Phosphonium-Substituted Ester Enolates as Synthetic Intermediates. A Novel Trialkylphosphine-Catalyzed Rearrangement of Allylic Acrylates

A novel Ireland-type rearrangement which utilizes a catalytic amount of a trialkylphosphine with allylic acrylates has been developed as a synthetic entry into α-methylene-γ,δ-unsaturated carboxylic acids.

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.

Phosphite-Mediated in Situ Carboxyvinylation: A New General Acrylic Acid Synthesis

Sequential treatment of a 2-halo carboxylic acid with a dialkyl phosphite and an aldehyde or ketone in the presence of 3 equiv of sodium hydride in glyme constitutes a new general acrylic acid synthesis superior to conventional methods.An alkoxide-in-alcohol variant may be used with bromo- or chloroacetic acid and aryl aldehydes to produce cinnamic acids conveniently.The scope and other features of the synthesis are discussed.