334-20-3Relevant articles and documents
New approach to the synthesis of 9-oxo-2E-decenoic acid, a multifunctional pheromone of queen honeybee, from the telomer of butadiene and water
Ishmuratov,Vydrina,Nasibullina,Yakovleva,Muslukhov,Tolstikov
, p. 789 - 791 (2012/03/27)
A new approach was proposed for the synthesis of 9-oxo-2E-decenoic acid, a multifunctional pheromone of queen honeybee (Apis mellifera L.), starting from the available telomer of butadiene and water (2E,7-octadien-1-ol) using in the key steps partial ozonolysis of the corresponding carbonyl compound, selective oxidation of the conjugated aldehyde into a carboxylic acid, and alkylation of acetoacetic ester to introduce the oxo group.
Practical synthesis of (E)-α,β-unsaturated carboxylic acids using a one-pot hydroformylation/decarboxylative Knoevenagel reaction sequence
Kemme, Susanne T.,?mejkal, Tomá?,Breita, Bernhard
supporting information; experimental part, p. 989 - 994 (2009/05/27)
Combining the regioselective room temperature/ambient pressure hydroformylation and a modification of the Doebner-Knoevenagel reaction allowed for the development of an efficient, one-pot procedure for the synthesis of (E)-α,β-unsaturated carboxylic acids. The reaction proceeds under mild conditions, tolerates a variety of functional groups and gives (E)-α,β-unsaturated carboxylic acids in good yields and with excellent regio-and stereocontrol. The practicability of this process has been demonstrated by a short protecting group-free synthesis of the queen honeybee pheromones 9-ODA[( E)-9-oxodec-2-enoic acid] and 9-HDA[( E)-9-hydroxydec-2-enoic acid].
Synthesis of a multifunctional pheromone of the honeybee Apis mellifera via condensation of 7-oxooctanal with malonic acid
Ishmuratov,Yakovleva,Botsman,Ishmuratova,Muslukhov,Khambalova,Tolstikov
, p. 28 - 30 (2007/10/03)
Condensation of 7-oxooctanal with malonic acid in a Doebner reaction produces 9-oxo-2E-decenoic acid (42% yield) and a comparable amount of products from Tishchenko disproportionation of the starting aldehyde (7-oxooctyl-7- oxooctanoate) and re-esterification by acetic acid (7-oxooct-1-ylacetate and 7-oxooctanoic acid).