140-10-3Relevant articles and documents
CINNAMAMIDE DERIVATIVES FROM CLAUSENA LANSIUM
Lin, Jer-Huei
, p. 621 - 622 (1989)
From the ether extract of the seeds of Clausena lansium, three new amide derivatives have been isolated, and their structures elucidated by chemical and spectroscopic methods.They were shown to be N-cis-styryl-cinnamamide, N-methyl-N-cis-styryl-cinnamamide and N-methyl-N-phenethyl-cinnamamide, which we have named lansiumamides A, B and C, respectively.In addition, a known amide, lansamide-I was identified. - Keywords: Clausena lansium; Rutaceae; cinnamamide; lansiumamides; lansamide-I; cinnamic acid derivative.
A Rapid and Efficient Microwave-Assisted Synthesis of Substituted 3-Phenylpropionic Acids from Benzaldehydes in Minutes
Sharma, Anuj,Joshi, Bhupendra P.,Sinha, Arun K.
, p. 1186 - 1187 (2003)
A convenient, inexpensive, and efficient synthesis of 3-phenylpropionic acids (1a-1f) by reacting benzaldehyde (2a-2f) and malonic acid in acetic acid and piperidine into cinnamic acid (3a-3f) in 77 to 89% followed by its reduction with PdCl2 in the biphase of formic acid and aqueous sodium hydroxide is reported under microwave irradiation which utilizes short reaction time ranging 5 to 7 min to provide 1a-1f in moderate to high yield (69-86%) depending upon methoxy, methylenedioxy, and hydroxy groups present at the phenyl ring.
Batatins I and II, ester-type dimers of acylated pentasaccharides from the resin glycosides of sweet potato
Escalante-Sanchez, Edgar,Pereda-Miranda, Rogelio
, p. 1029 - 1034 (2007)
Batatins I (1) and II (2), two ester-type dimers of acylated pentasaccharides, have been isolated by recycling HPLC from the hexane-soluble extract of sweet potato (Ipomoea batatas var. batatas). The structures were elucidated by a combination of high-resolution NMR spectroscopy and mass spectrometry. Complete analysis and unambiguous assignments of the 1H and 13C NMR spectra of 1 and 2 were achieved by 2D shift correlation measurements. The glycosidic acid forming each branched pentasaccharide monomelic unit was confirmed as simonic acid B. Three different fatty acids esterify this core at the same positions in both batatins: C-2 on the second rhamnose unit and C-4 and C-2 (or C-3) on the third rhamnose moiety. The acylating residues were identified as (+)-(2S)-methylbutanoic, dodecanoic (lauric), and cinnamic acids. The site of lactonization by the aglycon in unit A was placed at C-3 of the second saccharide. The position for the ester linkage for monomelic unit B on the macrocylic unit A was identified as C-3 of the terminal rhamnose?. Through spectroscopic simulation of these complex oligosaccharides, the chemical shifts and coupling constants were deduced for the overlapped proton resonances with a non-first-order resolution. The experimental NMR spectroscopic values registered for batatinoside I (3), a new polyacylated macroyclic pentasaccharide also isolated from this plant, were used as the starting point for spectral simulation of 1 and 2. Both polymers 1 and 2 represent dimers of compound 3.
Nickel-mediated regio- and chemoselective carboxylation of alkynes in the presence of carbon dioxide
Saito, Shinichi,Nakagawa, Satomi,Koizumi, Toru,Hirayama, Kyoko,Yamamoto, Yoshinori
, p. 3975 - 3978 (1999)
Alkynes are carboxylated in a highly regio- and chemoselective manner in the presence of Ni(cod)2, DBU, and CO2 to give the carboxylated products in good yields. The reaction was carried out under very mild conditions (CO2 1 atm, 0°C) in the presence of a stoichiometric amount of alkynes, conjugated enynes, or diynes. The high selectivity observed in the reaction would be explained in terms of the stability and the reactivity of the intermediates.
Alkylacylimidazoles in Claisen–Schmidt and Knoevenagel Condensations
Mei, X.,Ning, J.,Quan, H.,She, D.,Wang, L.,Wang, Zh.
, p. 1462 - 1467 (2020)
Abstract: Alkylacylimidazoles were shown to be good reagents for Claisen–Schmidt and Knoevenagel-like condensations. The Claisen–Schmidt condensation of N-acetylimidazole with benzaldehyde followed by acidification with HCl gave cinnamic acid. The Knoevenagel-like condensation of N-(acetoacetyl)imidazole with hydrated aldehydes resulted in a fast and efficient formation of β-hydroxyketones. The studied reactions provide a new and general synthetic approach to cinnamic acid derivatives and β-hydroxyketones, as well as a new application field of alkylacylimidazoles.
New iridoid glycoside from Gratiola officinalis
Ali, Liaqat,Rizvi, Tania Shamim,Ahmad, Manzoor,Shaheen, Farzana
, p. 1191 - 1195 (2012)
A new iridoid glycoside, 1β,6β-di-O-trans-cinnamoyl-9-O-β-D- glucopyranosyl-3-iridene-5β-ol (1), along with four known compounds loliolide (2), β-sitosterol-3-O-β-D-glucopyranoside (3), betulinic acid (4), and β-amyrin (5), was isolated from the aerial parts of Gratiola officinalis L. The structure of the new compound was deduced on the basis of 1D 1H and 13C NMR and 2D HMQC, HMBC, and COSY experiments, and mass spectrometric techniques (EI-MS and HR-EI-MS). The relative configuration of 1 was assigned by comparative analysis of the NMR spectral data with known analogs, together with NOESY experiments.
An Equilibrium Study of the Conversion of L-Phenylalanine to trans-Cinnamic Acid and Ammonia
Tewari, Yadu B.,Gajewsi, Ewa,Goldberg, Robert N.
, p. 904 - 909 (1987)
The thermodynamics of the enzymatic conversion (L-phenylalanine ammonia-lyase) of aqueous L-phenylalanine to trans-cinnamic acid and ammonia has been investigated by using high-performance liquid chromatography (HPLC).The reaction was carried out in 0.1 M Tris/HCl buffer containing ammonium chloride over the pH range 7.0-7.7, at ionic strength from 1.0 to 2.1 mol kg-1, and over the temperature range 285-316 K.Analysis of the HPLC data using an estimated heat capacity change of 50 J mol-1 K-1 and an ion-size parameter of 1.6 mol-1/2 kg1/2 leads to an equilibrium constant of 1.16 +/- 0.3 mol kg-1 and an enthalpy change of 24.8 +/- 2.0 kJ mol-1 at 298.15 K for the process L-phenylalanine+/-(aq) = trans-cinnamic acid-(aq) + NH4+(aq).The use of these thermodynamic parameters in an equilibrium model for this system allows for the prediction of values of the apparent equilibrium constant as a function of pH, temperature, and composition and also of the effect of these parameters on the optimal product yield of L-phenylalanine during its manufacture from trans-cinnamic acid and ammonia.The available thermochemical data for this generic type of reaction can be rationalized in terms of a scheme which views the entropy changes for related processes to be comparable and then attributes differences in Gibbs energy changes to differences in enthalpy changes which can be influenced by effects such as resonance stabilization of the double bonds which are formed.
Solid-supported reagents for the oxidation of aldehydes to carboxylic acids
Takemoto,Yasuda,Ley
, p. 1555 - 1556 (2001)
Solid-supported reagents such as phosphate-buffered (PB) silica gel (SiO2) supported potassium permanganate (KMnO4) and polymer-supported (PS) chlorite have been prepared and used in the conversion of aldehydes to carboxylic acids, affording products without any need for conventional work-up procedures.
Highly regioselective Friedel-Crafts alkylation of indoles with α,β-unsaturated N-acylbenzotriazoles
Zou, Xuefei,Wang, Xiaoxia,Cheng, Cungui,Kong, Lichun,Mao, Hui
, p. 3767 - 3771 (2006)
The Friedel-Crafts alkylation rather than acylation of indoles was realized with α,β-unsaturated acylbenzotriazoles catalyzed by samarium(III) iodide under reflux in anhydrous THF. The reaction was highly regioselective, and a series of new 3-substituted indole derivatives were obtained in moderate to good yields with the potential to be further transformed into various indole derivatives due to the presence of active acylbenzotriazole moiety.
"Fishing and hunting"-selective immobilization of a recombinant phenylalanine ammonia-lyase from fermentation media
Sánta-Bell, Evelin,Molnár, Zsófia,Varga, Andrea,Nagy, Flóra,Hornyánszky, Gábor,Paizs, Csaba,Balogh-Weiser, Diána,Poppe, László
, (2019)
This article overviews the numerous immobilization methods available for various biocatalysts such as whole-cells, cell fragments, lysates or enzymes which do not require preliminary enzyme purification and introduces an advanced approach avoiding the costly and time consuming downstream processes required by immobilization of purified enzyme-based biocatalysts (such as enzyme purification by chromatographic methods and dialysis). Our approach is based on silica shell coated magnetic nanoparticles as solid carriers decorated with mixed functions having either coordinative binding ability (a metal ion complexed by a chelator anchored to the surface) or covalent bond-forming ability (an epoxide attached to the surface via a proper linker) enabling a single operation enrichment and immobilization of a recombinant phenylalanine ammonia-lyase from parsley fused to a polyhistidine affinity tag.
