1851-90-7

Upstream product

• 3452-09-3 1-nonyne 
• 925-90-6 ethylmagnesium bromide 
• 124-38-9 carbon dioxide 
• 39247-28-4 1,1-dibromonon-1-ene 
• 15719-64-9 methylammonium carbonate 
• 74-96-4 ethyl bromide 
• 10297-09-3 oct-7-ynoic acid 
• 4117-14-0 2-decyn-1-ol 
• 124-13-0 Octanal 
• 4282-40-0 1-Iodoheptane 
• 471-25-0 Propiolic acid 

Downstream Products

• 3452-09-3 1-nonyne 
• 124-38-9 carbon dioxide 
• 7328-34-9 ethyl 2E,4E-decadienoate 
• 78910-33-5 sarmentine 
• 1374348-14-7 2-(non-1-ynyl)-5-phenyl-1,3,4-oxadiazole 
• 946434-95-3 C₁₈H₂₂O₃ 
• 67587-20-6 methyl 2-decynoate 

Relevant academic research and scientific papers

Synthesis of [1-11C]-2-octynoic acid, [1-11C]-2-decynoic acid and [1-11C]-3-(R,S)-methylocatanoic acid as potential markers for PET studies of fatty acid metabolism

[1-11C]-2-Octynoic acid, [1-11C]-2-decynoic acid and [1-11C]-3-(R,S)-methyloctanoic acid have been synthesized in order to evaluate these compounds as PET (Positron Emission Tomography) tracers for imaging in vivo medium-chain acyl-CoA dehydrogenase and medium-chain fatty acid utilization. The synthesis was performed by the Grignard reaction between alkylmagnesium bromides and [11C]CO2. The radiochemical yields of [1-11C]-2-octynoic acid, [1-11C]-2-decynoic acid, and [1-11C]-3-(R,S)-methyloctanoic acid were 10, 7 and 1% based on the [11C]CO2 used respectively. Radiochemical purity was >99% in all cases.

An Unsaturated Quinolone N-Oxide of Pseudomonas aeruginosa Modulates Growth and Virulence of Staphylococcus aureus

The pathogen Pseudomonas aeruginosa produces over 50 different quinolones, 16 of which belong to the class of 2-alkyl-4-quinolone N-oxides (AQNOs) with various chain lengths and degrees of saturation. We present the first synthesis of a previously proposed unsaturated compound that is confirmed to be present in culture extracts of P. aeruginosa, and its structure is shown to be trans-Δ1-2-(non-1-enyl)-4-quinolone N-oxide. This compound is the most active agent against S. aureus, including MRSA strains, by more than one order of magnitude whereas its cis isomer is inactive. At lower concentrations, the compound induces small-colony variants of S. aureus, reduces the virulence by inhibiting hemolysis, and inhibits nitrate reductase activity under anaerobic conditions. These studies suggest that this unsaturated AQNO is one of the major agents that are used by P. aeruginosa to modulate competing bacterial species.

CONTROLLING BIOFILMS WITH CYCLOPROPANATED FATTY ACIDS

Compositions and methods for using cyclopropanated structural analogs of fatty acid biofilm dispersal agents are characterized by superior biofilm dispersion. When used in combination with antimicrobials, these analogs decrease the minimum inhibitory concentration of antimicrobial agents required for eradication of the biofilm and/or treatment of infection. Methods for using these analogs include direct application to a surface, blending with lipid based carriers, or covalent anchoring the molecule to a surface.

Cu(I)-catalyzed macrocyclic Sonogashira-type cross-coupling

A macrocyclic Cu-catalyzed Sonogashira-type cross-coupling reaction has been developed that employs an operationally simple CuCl/phen/Cs 2CO3 catalyst system. Macrocyclizations can be performed at relatively high concentrations witho

Electrochemical selective incorporation of CO2 into terminal alkynes and diynes

Electrochemical incorporation of CO2 into terminal alkynes and diynes on silver cathodes occurred selectively, to afford monocarboxylic acid derivatives in good yields. The electrolyses were carried out in one-compartment cells fitted with magnesium anodes, under mild conditions.

Expedient synthesis of unsaturated amide alkaloids from Piper spp: Exploring the scope of recent methodology

The Sakai aryl aldehyde - cyclic ketone aldol - Grob fragmentation sequence was extended to cinnamaldehyde and cyclohexanone, and the product was elaborated to analogues of the alkaloid piperstachine. The effects of substituents on the reaction involving cinnamaldehyde were studied. The aldol-fragmentation sequence failed with benzaldehyde when cyclooctanone or cyclobutanone was substituted for cyclohexanone or cyclopentanone, and the reasons for this failure were examined. Four-carbon Wittig homologation of the piperonal-cyclobutanone aldol-fragmentation product, a hypothetical route to alkaloids such as retrofractamide A, was thus not viable. Instead, three-carbon homologation of the readily available piperonal-cyclopentanone product, using alkyne chemistry recently disclosed by Lu and Trost, afforded these alkaloids in excellent overall yield. The alkyne isomerization was also used to effect efficient syntheses of pellitorine and several other non-aromatic 2E,4E-dienoic Piper amide alkaloids. The Sakai aryl aldehyde - cyclic ketone aldol - Grob fragmentation sequence was extended to cinnamaldehyde and cyclohexanone, and the product was elaborated to analogues of the alkaloid piperstachine. The effects of substitutents on the reaction involving cinnamaldehyde were studied. The aldol-fragmentation sequence failed with benzaldehyde when cyclooctanone or cyclobutanone was substituted for cyclohexanone or cyclopentanone, and the reasons for this failure were examined. Four-carbon Wittig homologation of the piperonal-cyclobutanone aldol-fragmentation product, a hypothetical route to alkaloids such as retrofractamide A, was thus not viable. Instead, three-carbon homologation of the readily available piperonal-cyclopentanone product, using alkyne chemistry recently disclosed by Lu and Trost, afforded these alkaloids in excellent overall yield. The alkyne isomerization was also used to effect efficient syntheses of pellitorine and several other non-aromatic 2E,4E-dienoic Piper amide alkaloids.

Production of substituted acetylenic compounds

A method of producing substituted acetylenic compounds which comprises: reacting an organic compound having the general formula of wherein A represents a saturated or unsaturated aliphatic hydrocarbon residue of 1-20 carbon atoms which may have one or more substituents inactive in the reaction, and X represents a halogen atom or an arylsulfonyloxy group, with a metal acetylide having the general formula of wherein M represents an alkali metal, and B represents (a) a hydrogen, (b) a saturated or unsaturated hydrocarbon residue which may have one or more substituents inactive in the reaction, or (c) a saturated or unsaturated hydrocarbon residue which has a substituent having the general formula of wherein M represents an alkali metal, in the presence of an alkyl-2-imidazolidinone having the general formula of STR1 wherein R1 and R2 independently represent a lower alkyl, and R3 represents a hydrogen or a lower alkyl.