886-51-1

Upstream product

• 186581-53-3 diazomethane 
• 71555-80-1 3-((R)-1-Hydroxy-6,6,9-trimethyl-6a,7,10,10a-tetrahydro-6H-benzo[c]chromen-3-yl)-propionic acid 
• 29584-65-4 methyl (E)-3-[3,5-dimethoxyphenyl]-2-propenoate 
• 705-76-0 3,5-dimethoxybenzyl alcohol 
• 877-88-3 3,5-dimethoxybenzyl bromide 
• 2150-37-0 methyl 3,5-dimethoxybenzoate 
• 292638-85-8 acrylic acid methyl ester 
• 613-45-6 2,4-Dimethoxybenzaldehyde 
• 10272-07-8 3.5-dimethoxyaniline 
• 93092-27-4 methyl α-bromohydrocynnamate 
• 67-56-1 methanol 
• 730-01-8 2-(3',5'-Dimethoxyphenyl)-ethane-1,1-dicarboxylic acid 

Downstream Products

• 1080-05-3 3-(3,5-dimethoxyphenyl)-1-propanol 
• 436155-32-7 3-(3,5-dimethoxyphenyl)propanoylhydrazine 
• 156141-40-1 phenyl 2-[3-(3,5-dimethoxyphenyl)propanoyl]hydrazinecarboxylate 
• 156141-49-0 phenyl (6,8-dimethoxy-2-oxo-1,2,3,4-tetrahydroquinolin-1-yl)carbamate 
• 889-24-7 5-(3,5-dimethoxyphenyl)pentanoic acid 
• 91555-31-6 4-(3,5-dimethoxyphenyl)butanoic acid 
• 831-78-7 3-(3,5-dimethoxyphenyl)-1-bromopropane 
• 717-94-2 3-(3,5-dimethoxyphenyl)propionic acid 

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.

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.

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.

(+)-CANNABISPIRENONE-A: SYNTHESIS AND ABSOLUTE CONFIGURATION

An efficient asymmetric synthesis of cannabispirenone-A (1a) has been accomplished.The absolute configuration of the (+)-(1a) is assigned as R.The magnitude of rotation calls the optical purity of the natural product into question.

Synthesis of Methyl 4'',5''-Bisnor-Δ1,6-tetrahydrocannabinol Methyl Ether 3''-Oate - An Intermediate Cannabis Metabolite

The title compound (III), a convenient intermediate for metabolite synthesis, has been prepared by the condensation of 3-(3',5'-dihydroxyphenyl)propionic acid with (-)-trans-verbenol in the presence of boron trifluoride etherate and subsequent isolation a