821-96-5

Usage

InChI:InChI=1/C11H22/c1-3-5-7-9-11-10-8-6-4-2/h3,5H,4,6-11H2,1-2H3/b5-3-

Upstream product

• 18495-28-8 1-bromoundec-2-yne 
• 62872-77-9 (E)-3-benzenesulfonyl-2-undecene 
• 74-88-4 methyl iodide 
• 107-01-7 butene-2 
• 112-62-9 Methyl oleate 
• 187737-37-7 propene 
• 1120-21-4 n-Undecane 
• 104900-75-6 [((E)-Undec-2-ene)-3-sulfonyl]-benzene 
• 73377-32-9 N-n-undecyl-5,6,8,9-tetrahydro-7-phenyldibenzacridinium trifluoromethanesulfonate 
• 56956-46-8 undeca-1,2-diene 
• 100207-71-4 lauroyl cyanide 
• 8001-22-7 soybean oil 

Relevant academic research and scientific papers

Integrated extraction and catalytic upgrading of microalgae lipids in supercritical carbon dioxide

Fatty acids from microalgae are attractive compounds for catalytic upgrading to chemicals, but their extraction often requires multi-step procedures and the use of various organic solvents. To relieve this bottleneck, we propose a straightforward approach of combined extraction and catalytic functionalization via olefin cross-metathesis (ethenolysis and butenolysis) in supercritical CO2 (scCO2). This is demonstrated for Phaeodactylum tricornutum microalgae biomass. ScCO2 at optimum conditions (90 °C, 620 atm, ρ(CO2) = 0.90 g mL-1) extracted the lipids selectively and quantitatively from previously disrupted cells, while organic solvent extraction for comparison additionally extracted polar diacylglycerides and chlorophylls. In a one-pot approach, olefin cross-metathesis of the unsaturated fatty acids (FA16:1, FA18:1 and FA20:5) by alkenolysis yielded the desirable mid-chain olefin and unsaturated ester products. The product spectrum compares to alkenolysis of individual model compounds in scCO2 as well as of separately scCO2 extracted microalgae oil. Both these ethenolysis and butenolysis proceed with conversions of more than 81% and high selectivities to the desired products. This biorefinery approach was further illustrated by the simultaneous extraction and catalytic isomerizing alkoxycarbonylation in scCO2.

Hydroindation of allenes and its application to radical cyclization

Hydroindation of allenes and radical cyclization of 1,2,7-trienes (allenenes) were accomplished by HInCl2 with high regioselectivity to afford a variety of cyclic compounds. The resulting vinylic indiums could be used for successive coupling reactions in a one-pot procedure. The use of HInCl2 generated slowly in situ is extremely effective for the radical cyclization. The Royal Society of Chemistry.

SYNTHESIS OF TERMINAL ALKENES FROM INTERNAL ALKENES VIA OLEFIN METATHESIS

This disclosure relates generally to olefin metathesis, and more particularly relates to the synthesis of terminal alkenes from internal alkenes using a cross-metathesis reaction catalyzed by an olefin metathesis catalyst. According to one aspect, for example, a method is provided for synthesizing a terminal olefin, the method comprising contacting, in the presence of a ruthenium alkylidene metathesis catalyst, an olefinic substrate comprised of at least one internal olefin with a cross metathesis partner comprised of an alpha olefinic reactant, under reaction conditions effective to allow cross-metathesis to occur, wherein the reaction conditions include a reaction temperature of at least 35 °C. The methods, compositions, reactions and reaction systems herein disclosed have utility in the fields of catalysis, organic synthesis, and industrial chemistry.

METHODS OF MAKING MONOUNSATURATED FUNCTIONALIZED ALKENE COMPOUNDS BY METATHESIS

Described is a method of chemically modifying a starting composition comprising polyunsaturated alkene compounds in order to convert at least a portion of the polyunsaturated alkene compounds into functionalized monounsaturated alkene compounds. The separated monounsaturated alkene compounds may be useful, for example, as a starting material in the synthesis of organic chemicals such as diacids, diesters, and the like.

REDUCTION DE DERIVES D'ALCOOLS PROPARGYLIQUES CATALYSEE PAR UN COMPLEXE DE PALLADIUM ZEROVALENT

Catalysis by tetrakis(triphenylphosphine)palladium of the reaction of hydride donnors with secondary propargylic bromides, mesylates and phosphates increases markedly the amount of allene produced.The best results in that direction are obtained with mesylates and phosphates by using lithium triethylborohydride.The reaction then occurs with an ANTI introduction of the hydride with respect to the leaving group.A mechanism is proposed which explains the influence of the various parameters of the reaction.

ORGANIC SYNTHESIS WITH SULFONES. XXXVIII. ON THE MECHANISM OF THE STEREOSPECIFIC HYDROGENOLYSIS OF VINYLIC SULFONES BY SODIUM DITHIONITE.

The stereospecific hydrogenolysis of vinylic sulfones by sodium dithionite in a protic medium proceeds by addition of HSO2- to give an intermediate which could be isolated after alkylation in situ to a 1,2-bissulfone.The mechanism is therefore of the β-addition-elimination type.In the case of E-2-benzenesulfonyl-2-butene and ethyl iodide a single crystalline diastereoisomer was obtained and shown to have the threo configuration by X-ray crystallography.The addition step follows the syn and the elimination step the anti stereochemistry, thus accounting for the overall retention of configuration observed.

Palladium-Catalyzed Decarbonylation of Acyl Cyanides

The palladium-catalyzed decarbonylation of aromatic and heteroaromatic acyl cyanides 1 gives the corresponding nitriles 2 in excellent yields.Alkylacyl cyanides can be converted into the corresponding alkenes via decarbonylation followed by β-elimination of hydrogen cyanide.Because of easy preparation of acyl cyanides by the oxidation of cyanohydrins, the present decarbonylation reaction provides an efficient method for the preparation of nitriles from aldehydes under mild and neutral conditions.The catalytic decarbonylation involves the following processes; oxidative addition of acyl cyanides 1 to Pd(PPh3)4 to give acylpalladium complexes 13, acyl-aryl rearrangement, reductive elimination.When an acyl cyanide has a β-hydrogen, the intermediate cyanoalkylcarbonylpalladium (15) undergoes β-elimination to give alkenes.

The Conversion of Primary Amines into Olefins: a Mild Alternative to the Hofmann Elimination

Use of the pentacyclic pyrylium salt (1) allows a two-step conversion of the amine RR'CHCH2NH2 into RR'C=CH2 in high yield under mild conditions.