66417-42-3Relevant academic research and scientific papers
Pd-catalyzed dearboxylative heck coupling with dioxygen as the terminal oxidant
Fu, Zhengjiang,Huang, Shijun,Su, Weiping,Hong, Maochun
supporting information; experimental part, p. 4992 - 4995 (2010/12/25)
Pd-catalyzed decarboxylative Heck coupling of aromatic carboxylic acids with various olefins is developed using O2 as the terminal oxidant. Enhancement of O2 pressure leads to improving reaction turnover in this transformation and allows significantly reducing catalyst loading for efficient conversion of electron-rich benzoic acids. A Pd catalyst supported by a carbene ligand enables using electron-deficient benzoic acids as coupling partners.
Pd-catalyzed decarboxylative arylation of silyl enol ester sp3 β-C-H bond under aerobic conditions
Fu, Zhengjiang,Huang, Shijun,Kan, Jian,Su, Weiping,Hong, Maochun
supporting information; experimental part, p. 11317 - 11321 (2011/02/16)
Pd-catalyzed aerobic oxidative coupling of various benzoic acids with silyl enol esters proceeds via a combination of decarboxylation with sp3 β-C-H bond activation to give Heck-type products. Mechanistic studies reveal this coupling involves in situ generation of olefin from aerobic oxidation of silyl enolate, followed by decarboxylative Heck coupling.
Structure-activity relationships of phenylpropanoids as antifeedants for the pine weevil Hylobius abietis
Bohman,Nordlander,Nordenhem,Sunnerheim,Borg-Karlson,Unelius
, p. 339 - 352 (2008/09/18)
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
Sunnerheim, Kerstin,Nordqvist, Anneli,Nordlander, Goeran,Borg-Karlson, Anna-Karin,Unelius, C. Rickard,Bohman, Bjoern,Nordenhem, Henrik,Hellqvist, Claes,Karlen, Anders
, p. 9365 - 9372 (2008/03/17)
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.
Acid-labile anchor groups for the synthesis of peptide amides by a solid-phase method
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, (2008/06/13)
The invention relates to new compounds of the formula STR1 in which R1 denotes (C1 -C8)-alkyl, R2 denotes an amino acid residue which is protected with a urethane protective group which can be eliminated with weak acid or base, or denotes an amino protective group which can be eliminated with weak acid or base, R3 denotes hydrogen or (C1 -C4)-alkyl, and Y1 -Y9 denote identical or different radicals hydrogen, (C1 -C4)-alkyl, (C1 -C4)-alkoxy or --O--(CH2)n --COOH (with n=1 to 6), with one of these radicals being --O--(CH2)n --COOH, or Y1, Y2 and Y5 -Y9 denote identical or different radicals hydrogen, (C1 -C4)-alkyl or (C1 -C4)-alkoxy, Y3 denotes hydrogen or (C1 -C8)-alkoxy and Y4 denotes --(CH2)n --COOH or --NH--CO--(CH2)n --COOH (with n=1 to 6). Processes for the preparation thereof and the synthesis of peptide amides by a solid-phase method using these new compounds (spacers) are described.
Synthesis and Experimental Ionization Energies of Certain (E)-3-Arylpropenoic Acids and Their Methyl Esters
Peterson, John R.,Russell, Morley E.,Surjasasmita, Irawan B.
, p. 534 - 537 (2007/10/02)
Ionization energies for several methoxy-substituted (E)-3-arylpropenoic acids and methyl (E)-3-arylpropenoates were experimentally determined by mass spectroscopy.The title compounds were prepared in excellent yield by Knoevenagel condensation of an aromatic aldehyde with malonic acid and by Fischer esterification of the acid with methanol.
2-Hydroxy-4-methoxy-trans-cinnamic Acid as a Precursor of Herniarin in Artemisia dracunculus
Hofer, Otmar,Szabo, Geza,Greger, Harald
, p. 1219 - 1222 (2007/10/02)
The isolation of (E)-2-hydroxy-4-methoxycinnamic acid (1) from Artemisia dracunculus L. supports strongly the assumption that this compound is an intermediate in the biosynthesis of 7-methoxycoumarin (herniarin, 3).The structure of the UV-unstable compound 1 was derived from 1H-NMR data and by comparison of the stable dimethylated derivative with synthetic (E)-2,4-dimethoxycinnamic acid methyl ester (2). - Keywords: Coumarins; Biosynthesis; Herniarin; Artemisia dracunculus; Compositae
