112-38-9Relevant articles and documents
A facile and selective cleavage of prenyl esters catalyzed by CeCl3·7 H2O-NaI
Yadav,Subba Reddy,Venkateshwara Rao,Chand,Prasad
, p. 137 - 139 (2002)
A highly selective cleavage of prenyl esters has been achieved in high yields using CeCl3·7 H2O-NaI in refluxing acetonitrile under neutral conditions. This method is mild and compatible with a wide variety of functional groups such
Useful Direct Conversion of Tetrahydropyranyl Ethers of Fatty Alcohols into Fatty Acids
Gruiec, Regine,Noiret, Nicolas,Patin, Henri
, p. 1083 - 1085 (1995)
Tetrahydro-2-pyranyl ethers from fatty primary alcohols can be converted in a one-step procedure into the corresponding carboxylic acids in high yields.This process avoids the synthesis of symmetrical esters, particularly for long-chain compounds.This reaction proved to be useful, for instance, to produce polyunsaturated fatty acids immediately before their biological testing. - Key words: Oxidation; polyunsaturated fatty acids; tetrahydropyranyl ethers
Interaction of oxygen functionalized alkenes with a methylaluminoxane-zirconocene catalyst studied by NMR
Helaja, Tuulamari,Hakala, Kimmo,Helaja, Juho,Loefgren, Barbro
, p. 164 - 176 (1999)
Reactions of hydroxyl, ether and carbonyl functionalized alkenes with methylaluminoxane prepared in toluene-d8 (MAO) and zirconocenedichloride (Cp2ZrCl2) were investigated by 1H- and 13C-NMR spectroscopy at 27°C. The 11 alkenes studied bear a terminal C=C bond separated by 7-9 (-CH2-) units from the heteroatom moiety. Intramolecular connectivities in mono (alkene), bi (alkene and MAO) and tri (alkene, MAO and Cp2ZrCl2) component mixtures were determined by 2D HSQC, HMBC, ROESY and NOESY NMR techniques. The five studied alkenols formed aluminium alkoxides with MAO even in the case of a substantial steric hindrance around the OH group. Zirconocene enhanced the formation of aluminium alkoxides. Decomposition to free alkenol was observed only for the straight chain alkenol (10-undecen-1-ol). The OTMS derivatives formed dimers of the type CH2=CR1R2 along with methyl derivatives, CH2=C(Me)(R) and (Me)CH=CH(R), in the presence of MAO and Cp2ZrCl2. 10-Undecenyl methyl ether and methyl decenoate remained mainly as a free comonomer in the presence of MAO or MAO/Cp2ZrCl2, though a transient coordination of the former to MAO was deduced. Unsaturated species Me2C=CH-Al-X and CH2=CH(CH2)5CH2CH=C(t-Bu)O-Al-X (X = MAO oligomer) were formed in the reaction of t-butyl undecenoate or 2,2-dimethyl-11-dodecen-3-one with MAO or MAO/Cp2ZrCl2. Interaction of the CH2=CH part of the functionalized alkenes with zirconocene was not observed. A possible coordination of the C=C bond to MAO was observed only for the sec alkenols.
A simple, mild and efficient procedure for selective cleavage of prenyl esters using silica-supported sodium hydrogen sulphate as a heterogenous catalyst
Ramesh,Mahender,Ravindranath,Das, Biswanath
, p. 1465 - 1467 (2003)
Prenyl esters were selectively and efficiently cleaved under slightly acidic reaction conditions using silica-supported sodium hydrogen sulfate as a heterogenous catalyst at room temperature to regenerate the parent carboxylic acids in very high yields.
A New and Efficient Synthesis of Trifluoromethyl Ketones from Carboxylic Acids. Part I.
Boivin, Jean,El Kaim, Laurent,Zard, Samir Z.
, p. 2573 - 2584 (1995)
Trifluoromethyl ketones can be prepared in good yield from primary carboxylic acid chlorides by reaction with pyridine and trifluoroacetic anhydride followed by aqueous work up.
Bio-based α,ω-Functionalized Hydrocarbons from Multi-step Reaction Sequences with Bio- and Metallo-catalysts Based on the Fatty Acid Decarboxylase OleTJE
Bojarra, Samiro,Reichert, Dennis,Grote, Marius,Baraibar, álvaro Gómez,Dennig, Alexander,Nidetzky, Bernd,Mügge, Carolin,Kourist, Robert
, p. 1192 - 1201 (2018)
OleT from Jeotgalicoccus sp. ATCC 8456 catalyzes the decarboxylation of ω-functionalized fatty acids to the corresponding alkenols, which can themselves serve as starting material for the synthesis of polymers and fine chemicals. To show the versatility of possible reactions, a series of in vitro reaction cascades was developed where an alkenol produced by the decarboxylation of ω-hydroxy fatty acids can be further converted into alkenylamines and diols. By coupling OleT with an alcohol dehydrogenase or alcohol oxidase as well as an amino-transaminase, an oxidative decarboxylation followed by the oxidation of the terminal alcohol and a subsequent reductive transamination could be carried out. By using different cofactors or electron sources, the reactions could be performed sequentially or simultaneously. The combination of enzymatic decarboxylation with a ruthenium catalyst in a chemo-enzymatic cascade provides a novel way to synthesize long-chain diols.
Oxidation of Primary Alcohols and Aldehydes to Carboxylic Acids via Hydrogen Atom Transfer
Tan, Wen-Yun,Lu, Yi,Zhao, Jing-Feng,Chen, Wen,Zhang, Hongbin
supporting information, p. 6648 - 6653 (2021/09/08)
The oxidation of primary alcohols and aldehydes to the corresponding carboxylic acids is a fundamental reaction in organic synthesis. In this paper, we report a new chemoselective process for the oxidation of primary alcohols and aldehydes. This metal-free reaction features a new oxidant, an easy to handle procedure, high isolated yields, and good to excellent functional group tolerance even in the presence of vulnerable secondary alcohols and tert-butanesulfinamides.
Nitrogen-fixing of ultrasmall Pd-based bimetallic nanoclusters on carbon supports
Chen, Ping,Liang, Hai-Wei,Shen, Shan-Cheng,Wang, Lei,Xu, Shi-Long,Yin, Peng,Zhang, Le-Le
, p. 297 - 304 (2020/07/03)
Synthesis of supported Pd-based bimetallic catalysts is of great importance in the heterogeneous catalysis field owing to their optimal geometric and electronic effects. Downsizing active metals to ultrasmall nanocluster (2-reduction at 400–500 °C. Through the nitrogen-fixing strategy, we prepare 9 sub-2 nm Pd-based bimetallic nanocluster catalysts by conventional impregnation process. The prepared supported bimetallic Pd-Pb nanocluster catalyst exhibit a high turnover frequency of 1092 h?1 for the semihydrogenation of phenylacetylene under a mild condition (30 °C, 5 bar H2), along with a high selectivity of >93% to styrene, demonstrating the alloying and small-size effects in the bimetallic nanocluster catalysts.
Synthesis from Undecylenic Acid of Macroheterocycles with Diacylhydrazine and Ester Fragments
Mingaleeva,Yakovleva,Ishmuratov, G. Yu.
, p. 895 - 898 (2019/11/03)
A three-step synthesis of potentially biologically active 30- and 32-membered macroheterocycles with esters and acylhydrazines starting from methyl undecylenate was developed based on [1+1]-condensation of intermediate tetraesters, i.e., bis(10′ -methoxy-10′-oxodecyl)- or bis(11′-methoxy-11′ -oxoundecyl)hexanedioate, with hydrazine hydrate. The structures of the synthesized compounds were confirmed using IR and NMR spectroscopy and mass spectrometry.
Broadly Applicable Ytterbium-Catalyzed Esterification, Hydrolysis, and Amidation of Imides
Guissart, Céline,Barros, Andre,Rosa Barata, Luis,Evano, Gwilherm
, p. 5098 - 5102 (2018/09/13)
An efficient, broadly applicable, operationally simple, and divergent process for the transformation of imides into a range of carboxylic acid derivatives under mild conditions is reported. By simply using catalytic amounts of ytterbium(III) triflate as a Lewis acid promoter in the presence of alcohols, water, amines, or N,O-dimethylhydroxylamine, a broad range of imides is smoothly and readily converted to the corresponding esters, carboxylic acids, amides, and Weinreb amides in good yields. This method notably enables an easy cleavage of oxazolidinone-based auxiliaries.
