19367-39-6

Upstream product

• 33527-94-5 4-acetoxyiodobenzene 
• 292638-85-8 acrylic acid methyl ester 
• 3943-97-3 methyl p-hydroxycinnamate 
• 108-24-7 acetic anhydride 
• 7400-08-0 p-Coumaric Acid 
• 27914-73-4 4-acetoxybenzoyl chloride 
• 1384879-86-0 (E)-methyl 3-[2-(4-acetoxystyryl)phenyl]-3-oxopropanoate 
• 27542-85-4 4-acetoxycinnamic acid 
• 77-78-1 dimethyl sulfate 
• 108-59-8 malonic acid dimethyl ester 
• 123-08-0 4-hydroxy-benzaldehyde 
• 7400-08-0 para-coumaric acid 
• 3943-97-3 methyl 4-hydroxycinnamate 

Downstream Products

• 54965-55-8 methyl 3-(4-acetyloxyphenyl)propanoate 
• 20649-40-5 (E)-4-(3-hydroxyprop-1-enyl)phenol 
• 1552301-92-4 2-[4-(4-hydroxyphenyl)-2-oxochroman-6-yl]ethyl methyl carbonate 
• 1552302-02-9 3-(2-hydroxy-5-(2-hydroxyethyl)phenyl)-3-(4-hydroxyphenyl)propanoic acid 
• 120442-73-1 (E)-4-hydroxycinnamyl alcohol 4-O-β-D-glucopyranoside 
• 10210-17-0 3-(4-hydroxyphenyl)propan-1-ol 
• 922151-70-0 methyl 2-[4-(acetyloxy)phenyl]cyclopropanecarboxylate 
• 3943-97-3 methyl 4-hydroxycinnamate 

Relevant academic research and scientific papers

Synthesis of (±)-cartorimine

Heating pyranulose 4 and cinnamate 2 in the presence of 2,6-di-t-butylpyridine in CH3CN afforded the [5+2] cycloadduct, which was hydrolyzed to give 13% of cartorimine (1).

A practical, chemoselective approach to O-methylation of carboxylic acids with dimethyl malonate

A practical and chemoselective method is described for the O-methylation of carboxylic acids. Dimethyl malonate, a low toxic and commercially available compound was found to be an effective methylating reagent for a variety of carboxylic acids affording methyl ester products in good to high yields and with excellent chemoselectivity, without the use of strong bases as additives. A mechanism involving the utilization of potassium bromide is tentatively proposed.

Synthesis and DPPH radical scavenging activity of novel compounds obtained from tyrosol and cinnamic acid derivatives

Tyrosol, a naturally occurring phenolic compound poorly attractive as an antioxidant because of its weak efficacy, was used as starting material to obtain novel compounds. The synthesis is based on a trifluoroacetic acid-mediated hydroarylation of cinnamic esters with tyrosol to produce 4-aryl-3,4-dihydrocoumarins, molecules of biological interest, followed by a basic hydrolysis to give the corresponding ring opening products. Unreported mechanistic investigations confirmed that the first step resulted from an electrophilic aromatic substitution and an intramolecular transesterification. Final products exhibited DPPH radical scavenging activity significantly higher than tyrosol.

Pd-catalyzed sequential C-C bond formation and cleavage: Evidence for an unexpected generation of arylpalladium(II) species

A Pd(II)-catalyzed reaction engaging alkenyl β-keto esters is reported that leads to the formation of 1-naphthols and an unexpected generation of arylpalladium(II) species. Interception of the in situ generated arylpalladium(II) species in a Mizoroki-Heck reaction, together with additional mechanistic studies, provided strong evidence in support of the first aromatization-driven β-carbon elimination process. A single Pd catalyst served to promote a series of both C-C bond forming and cleavage events in an unprecedented manner.

CYCLOPROPANECARBOXYLIC ACID COMPOUND

A compound of the formula (I): wherein each symbol is as defined in the description, a salt thereof, and a prodrug thereof of the present invention unexpectedly have a superior GPR40 receptor agonist activity and superior properties as pharmaceutical prod

Synthesis of the 5-hydroxymethyl-6-aryl-8-oxabicyclo[3.2.1]oct-3-en-2-one natural products descurainin and cartorimine

Reaction of pyranulose 6 with styrenes 12c or 13 and Et3N in CH2Cl2 at 25 °C afforded the [5+2] cycloadducts 14c and 15, which were hydrolyzed to give the natural products 1 and descurainin (2) in 24 and 27% overall yield, respectively. Heating pyranulose 6 with cinnamate ester 21 in the presence of 2,6-di-t-butylpyridine in CH3CN at 175 °C afforded the [5+2] cycloadduct, which was hydrolyzed to give cartorimine (3) in 13% yield.

Assembled catalyst of palladium and non-cross-linked amphiphilic polymer ligand for the efficient heterogeneous Heck reaction

The efficient heterogeneous Heck reaction was achieved by a new networked and supramolecular catalyst PdAS-V (1b). Employing of PdAS-V in 5.0×10-5molequiv. efficiently progressed the heterogeneous Heck reaction of a series of aryl iodides with acrylates, styrenes and acrylic acid. PdAS-V was successfully recycled five times without any decrease in its activity, and showed good stability in toluene and water, and hence the Heck reaction was efficiently performed in both reaction media. The use of 8.0×10-7molequiv. of PdAS-V resulted in the coupling product in 92% yield with the turnover number (TON) and the turnover frequency (TOF) of PdAS-V reached up to 1,150,000 and 12,000, respectively. The efficient synthesis of resveratrol was achieved via the PdAS-V-promoted Heck reaction.

An efficient heterogeneous Heck reaction promoted by a new assembled catalyst of palladium and non-cross-linked amphiphilic polymer

A newly assembled insoluble catalyst 1b composed of palladium and non-cross-linked amphiphilic polymer was developed. It was named PdAS-V: a supramolecular complex of (NH4)2PdCl4 (2) and poly[(N-isopropylācrylamide)5?