849924-51-2

Usage

Physical State

Colorless liquid

Odor

Strong

Usage

Production of fragrances, chemical intermediate in the synthesis of other organic compounds

Classification

Volatile organic compound (VOC)

Flammability

Flammable

Obtained Through

Catalytic cracking of petroleum fractions, pyrolysis of natural gas liquids

Environmental Impact

Contributes to smog and ground-level ozone formation, regulated in some regions due to negative air quality impact.

Upstream product

• 56318-73-1 (Z)-3-undeca-1,3-dien-5-yne 
• 1457-42-7 pyridazinyl-N-oxide 
• 61307-38-8 1-heptynylmagnesium bromide 
• 109921-65-5 (Z)-hept-1-enylmagnesium bromide 
• 85615-59-4 (Z)-1-(Prop-2-ene-1-sulfonyl)-oct-2-ene 
• 19883-26-2 (3Z,5Z)-1,3,5-undecatriene 
• 141695-20-7 (2E,4Z)-nona-2,4-dienoyltriphenylsilane 
• 132213-08-2 (Z)-1-Chloro-undec-2-en-5-yne 
• 132213-11-7 (Z)-Undec-5-en-3-yn-1-ol 
• 132213-12-8 (3E,5Z)-Undeca-3,5-dien-1-ol 
• 132213-13-9 1-Heptynylmagnesium chloride 
• 85615-56-1 (E)-1-(Prop-2-ene-1-sulfonyl)-buta-1,3-diene 
• 141695-23-0 (2Z,4E,6Z)-3-triphenyl-2,4,6-undecatriene 
• 138039-05-1 (Z)-1,5-undecadien-3-yne 

Relevant academic research and scientific papers

Acetylenic silyl ketone as polysynthetic equivalent of useful building blocks in organic synthesis

Ethynyl silyl ketone 1 proved to be a very efficient Michael acceptor in carbocupration and metallocupration reactions. In particular, when using carbocuprates, a smooth entry to polyenals can be obtained, while, when using metallocuprates, silyl- and stannylpropenoyl silanes may be obtained, very powerful intermediates in organic synthesis.

STEREOSPECIFIC SYNTHESIS OF 1,5-DIEN-3-YNES AND 1,3,5-TRIENES. APPLICATION TO THE STEREOCHEMICAL IDENTIFICATION OF TRIENIC SEX PHEROMONES

A one-pot sterospecific synthesis of 1,5-dien-3-ynes (Z) or (E) is described, based upon a palladium-catalyzed cross-coupling reaction between butenynylzinc bromide, generated in situ from 1,1-difluoroethylene, and an adequate iodoalkene.These dienynes are converted into the corresponding trienic compounds by (Z) semi-hydrogenation.

Two new stereoselective syntheses of (3E,5Z)-1,3,5-undecatriene

Two new and short syntheses of (3E,5Z)-1,3,5-undecatriene 1 are presented. Both approaches are based on the coupling between a C7 and a C4 synthon and afford 1 in 92-96% stereoisomeric purity.

NOUVELLE SYNTHESE DES UNDECATRIENES-1,3,5 NATURELS

The two natural 1,3,5-undecatrienes have been synthesized starting from pyridazine-1-oxide.The methode allows us to obtain a mixture, in which the 1,3E,5Z isomer predominates.

A NOVEL SYNTHESIS OF LINEAR POLYENES VIA CONJUGATE ADDITION OF CUPRATES TO α,β-γ,δ-DIUNSATURATED SULFONES FOLLOWED BY SO2 EXTRUSION

The two 1,3-butadienyl 2-propenyl sulfones 5 and 6, 1,3,5-heptatriene synthons, have been transformed into the tri- and tetraenes 1 - 4 by alkylcuprate addition and Ramberg-Baecklund SO2 extrusion.The reaction stereochemistry is discussed.