65953-99-3

Upstream product

• 10538-48-4 2,3-dimethoxyhydrocinnamic acid 
• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 7345-82-6 trans-2,3-dimethoxycinnamic acid 
• 15854-60-1 methyl 3-(2,3-dimethoxyphenyl)propenoate 

Downstream Products

• 52644-01-6 5,6-dimethoxy-2-tetralone 
• 63307-15-3 4-(2,3-Dimethoxy-phenyl)-1-methanesulfinyl-butan-2-one 

Relevant academic research and scientific papers

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.

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.

Solid-supported green synthesis of substituted hydrocinnamic esters by focused microwave irradiation

An efficient chemoselective hydrogenation protocol for substituted cinnamic esters is developed for the synthesis in quantitative yield of corresponding bioactive dihydrocinnamic esters with solid-supported palladium chloride/ammonium formate (cat.) in HCOOH/H2O 1:2 as a hydrogenating agent under focused-microwave irradiation for 10 min.

Synthesis and anticholinesterase activity of huperzine a analogues containing phenol and catechol replacements for the pyridone ring

Based upon modeling results obtained using the crystal structure of huperzine A in complex with acetylcholinesterase (AChE), two novel analogues of this potent AChE inhibitor were designed with phenol or catechol rings replacing the pyridone ring. From the modeling studies, the catechol analogue appeared capable of replacing one of the crystallographic waters bridging huperzine with Tyr 130 and Glu 199 of AChE. The synthesis of these materials by use of a palladium catalyzed bicycloannulation strategy is detailed together with the results of AChE inhibition assays.