29417-96-7

Upstream product

• 67-56-1 methanol 
• 3029-79-6 3-methylcinnamic acid 
• 292638-85-8 acrylic acid methyl ester 
• 108-88-3 toluene 
• 3751-48-2 3-(3-methylphenyl)propanoic acid 
• 100-80-1 3-methylstyrene 
• 201230-82-2 carbon monoxide 
• 34386-38-4 1-(1-methoxyethyl)-3-methylbenzene 
• 529-20-4 2-methylphenyl aldehyde 
• 1779-58-4 (methyloxycarbonylmethyl)triphenylphosphonium bromide 
• 82444-40-4 (E)-methyl 3-methylcinnamate 

Downstream Products

• 95416-60-7 3-(3-methylphenyl)propanal 
• 111171-94-9 3-(m-methylphenyl)-1-propanol 

Relevant academic research and scientific papers

Aldehyde as a Traceless Directing Group for Regioselective C-H Alkylation Catalyzed by Rhodium(III) in Air

The aromatic aldehyde as a traceless directing group for the regionselective C-H alkylation catalyzed by rhodium(III) under aerobic atmospheric conditions has been developed. The process involves an aldehyde assisted direct addition of C-H bond to unsaturated electrophiles of acrylates or acrylic acids, and the subsequent decarbonylation. A trace amount of water is found to favor the reaction.

Palladium-Catalyzed Alkoxycarbonylation of sec-Benzylic Ethers

Herein, we report the palladium-catalyzed synthesis of 3-arylpropionate esters starting from secondary benzylic ethers. With this investigation it could be shown that ethers are suitable starting materials in addition to the established carbonylation reactions of olefins, alcohols, or aryl halides.

Cobalt(II)-Catalyzed Alkoxycarbonylation of Aliphatic Amines via C-N Bond Activation

The first cobalt-catalyzed deaminative alkoxycarbonylation reaction was described for the conversion of readily available primary alkyl amines to synthetically versatile esters with moderate to high yields. This transformation shows good functional group compatibility and can serve as a powerful tool for the modification of alkyl amine-containing complex natural products and drug molecules.

Synthesis method of dihydrocinnamate type compound

The invention discloses a synthesis method of a dihydrocinnamate type compound. The method takes a dichloro(pentamethylcyclopentadienyl)rhodium dimer as a catalyst and a formyl o-C-H bond of aromaticaldehyde and alpha,beta-unsaturated ester type compound

Comparison of Phenylacetates with Benzoates and Phenylpropanoates as Antifeedants for the Pine Weevil, Hylobius abietis

This study concludes an extensive investigation of antifeedants for the pine weevil, Hylobius abietis (Coleoptera: Curculionidae), an economically important pest of planted conifer seedlings. Building on the previously reported antifeedant effects of benzoates and phenylpropanoids (aromatic compounds with one- or three-carbon-atom substituents on the benzene ring), we here report the antifeedant effects of compounds with two-carbon-atom side chains (i.e., phenylacetates). We also present new results; the best antifeedants from the benzoate class were tested at 10-fold lower concentrations in order to find the optimal antifeedants. Generally, for all three compound classes, efficient antifeedants were found to have one or two methyl, chloro, or methoxy substituents on the aromatic ring. For monosubstituted phenylpropanoids, the substituent preferably should be in the para-position. In the search for synergistic antifeedant effects among the three compound classes, combinations of compounds from the three classes were tested in binary and ternary mixtures.

A recyclable CO surrogate in regioselective alkoxycarbonylation of alkenes: Indirect use of carbon dioxide

Herein, we report a Pd-catalysed alkoxycarbonylation of alkenes based on the use of a recyclable CO2 reduction product, the crystalline and air-stable N-formylsaccharin, as a CO surrogate. The carbonylation proceeds under ambient conditions in an exceptionally complementary regioselective fashion yielding the desired branched products from styrene derivatives and valuable linear esters from alkyl-substituted alkenes.

Structure-activity relationships of phenylpropanoids as antifeedants for the pine weevil Hylobius abietis

Ethyl cinnamate has been isolated from the bark of Pinus contorta in the search for antifeedants for the pine weevil, Hylobius abietis. Based on this lead compound, a number of structurally related compounds were synthesized and tested. The usability of the Topliss scheme, a flow diagram previously used in numerous structure-activity relationship (SAR) studies, was evaluated in an attempt to find the most potent antifeedants. The scheme was initially followed stepwise; subsequently, all compounds found in the scheme were compared. In total, 51 phenylpropanoids were tested and analyzed for SARs by using arguments from the field of medicinal chemistry (rational drug design). Individual Hansch parameters based on hydrophobicity, steric, and electronic properties were examined. The effects of position and numbers of substituents on the aromatic ring, the effects of conjugation in the molecules, and the effects of the properties of the parent alcohol part of the esters were also evaluated. It proved difficult to find strong SARs derived from single physicochemical descriptors, but our study led to numerous new, potent, phenylpropanoid antifeedants for the pine weevil. Among the most potent were methyl 3-phenylpropanoates monosubstituted with chloro, fluoro, or methyl groups and the 3,4-dichlorinated methyl 3-phenylpropanoate.

Novel Compounds

There is provided a compound of formula (I): processes for the manufacture thereof, pharmaceutical compositions thereof and uses in therapy.

Quantitative structure-activity relationships of pine weevil antifeedants, a multivariate approach

Antifeedant activity of mainly phenylpropanoic, cinnamic, and benzoic acids esters was tested on the pine weevil, Hylobius abietis (L.). Of 105 compounds screened for activity, 9 phenylpropanoates, 3 cinnamates, and 4 benzoates were found to be highly active antifeedants. To understand the structure-activity relationships of these compounds, a multivariate analysis study was performed. A number of molecular and substituent descriptors were calculated and correlated to results from two-choice feeding tests with H. abietis. Three local models were developed that had good internal predictive ability. External test sets showed moderate predictivity. In general, low polarity, small size, and high lipophilicity were characteristics for compounds having good antifeedant activity.

Synthesis and biological activity of new 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) synthase inhibitors: 2-oxetanones with a side chain mimicking the folded structure of 1233A.

To mimic the folded side chain conformation of 1233A (1), which is a 3-hydroxy-3-methylglutaryl coenzyme A (HMG-CoA) synthase inhibitor, 1233A analogs with aromatic rings in the side chain were synthesized. The 2-oxetanone moiety was kept intact. Among 1233A and its synthetic analogs, trans-3-hydroxymethyl-4-[2-(7-methoxycarbonyl-1-naphthyl)ethyl]-2-oxe tanone (23) showed the highest HMG-CoA synthase inhibitory activity in vitro. The structure-activity relationship at the side chain is discussed.