166432-52-6

Usage

Uses

Used in Fragrance Industry:
(3E)-Undeca-1,3-dien-5-yne is used as a fragrance ingredient for its nice fruity, green, and strong violet-leaf note. It adds a unique and pleasant aroma to various products, making it a valuable component in the creation of perfumes, colognes, and other scented products.
Used in Flavor Industry:
In the flavor industry, (3E)-undeca-1,3-dien-5-yne is used as an additive to enhance the taste and aroma of various food and beverage products. Its fruity and green notes contribute to a more complex and appealing flavor profile, making it a sought-after ingredient in the development of new and innovative flavors.
Used in Alternative Compounds:
(3E)-Undeca-1,3-dien-5-yne is also used as an alternative to other compounds like methyl octynoate and methyl nonynoate. This makes it a versatile option for chemists and researchers looking to explore new possibilities in the synthesis of various chemical compounds and materials.

Synthesis Reference(s)

Synthetic Communications, 24, p. 2273, 1994 DOI: 10.1080/00397919408019052

Trade name

Violettyne MIP (Firmenich).

InChI:InChI=1/C11H16/c1-3-5-7-9-11-10-8-6-4-2/h3,5,7H,1,4,6,8,10H2,2H3/b7-5+

Upstream product

• 110-53-2 1-Bromopentane 
• 10420-90-3 1,3-hexadien-5-yne 
• 66426-94-6 diethyl-undec-2-en-4-ynyl-amine 
• 1846-68-0 oct-2-ynal 
• 13361-64-3 trimethyl(propargyl)silane 
• 53915-69-8 allenyltributylstannane 
• 628-71-7 1-Heptyne 
• 78651-47-5 (E)-dec-2-en-4-yn-1-al 
• 19493-09-5 Methylenetriphenylphosphorane 
• 16195-87-2 (E)-dec-2-en-4-yl-1-ol 
• 16503-25-6 1-chloro-1E,3-butadiene 
• 10033-99-5 (1Z)-1-chloro-1,3-butadiene 
• 64146-57-2 1-heptynylzinc chloride 
• 3536-96-7 vinylmagnesium chloride 

Downstream Products

• 85615-64-1 undecatriene-2Z,4Z,6E 

Relevant academic research and scientific papers

Stereospecific Syntheses and Spectroscopic Properties of Isomeric 2,4,6,8-Undecatetraenes. New Hydrocarbons from the Marine Brown Alga Giffordia mitchellae

Giffordene (=(2Z,4Z,6E,8Z)-2,4,6,8-undecatetraene; 9f) and five stereoisomers are new C11H16 hydrocarbons from the marine brown alga Giffordia mitchellae.Their synthesis is based on non-stereoselective Wittig reactions of (E)-2-alkenals with appropriate acetylenic phosphoranes and subsequent chromatographic separation of the resulting (E/Z)-pairs.The uniform enynes (>98percent purity) are then stereospecifically reduced to (Z)-alkenes with Zn(Cu/Ag) in aq.MeOH at r.t. 13C- and 1H-NMR data of the new tetraenes are presented.Biosynthetically, giffordene (9f) originates from dodeca-3,6,9-trienoic acid via an unstable (3Z,5Z,8Z)-1,3,5,8-undecatetraene followed by a thermally allowed antarafacial 1,7-sigmatropic hydrogen shift to the (2Z,4Z,6E,8Z)-isomer 9f.

A short and efficient synthesis of (3E,5Z)-1,3,5-undecatriene from (1E)- 1-chloro-1,3-butadiene

A short synthesis of (3E,5Z)-1;3,5-undecatriene (cis-galbanolene) is described. The key step is the Pd/Cu-catalyzed coupling reaction of (E)-1- chloro-1,3-butadiene with 1-alkynes followed by stereoselective zinc reduction of the triple bond.

PROCESS FOR PREPARING DIENE

The present invention relates to the field of organic synthesis and more specifically it concerns a process for preparing compound of formula (I) catalyzed by a nickel complex. The compound of formula (II) is also part of the invention.

METHOD FOR PRODUCING 1,3-UNDECADIEN-5-YNE

PROBLEM TO BE SOLVED: To provide a method for producing 1,3-undecadien-5-yne useful as a fragrance material or a raw material therefor, the method being able to be carried out industrially in a short process from raw materials which are easy both to acquire and to handle. SOLUTION: The method for producing 1,3-undecadien-5-yne of formula 4 comprises: reacting croton aldehyde of formula 1 with a 1-heptynyl metal reagent such as 1-heptynyl magnesium bromide of formula 2 and the like to obtain an unsaturated alcohol of formula 3; and, thereafter, making an acid catalyst such as p-toluenesulfonic acid and the like on the unsaturated alcohol to perform a dehydration reaction. In the formula 2, M is lithium, sodium, zinc halide, or magnesium halide. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT

An efficient synthesis of stereodefined enynes and dienes via Pd-catalyzed reaction of chloroenynes and chlorodienes with Grignard reagents

In the presence of PdCl2(PPh3)2 and Et3N, chloroenynes and chlorodienes react rapidly under mild conditions with various Grignard reagents to give isomerically pure conjugated enynes, dienes, dienynes and triene

AgAsF6 as safe alternative to AgClO4 for generating cationic zirconocene species: Utilities in Lewis acid-promoted selective C---C bond forming reactions

For generating cationic zirconocene species that are useful for organic synthesis, AgAsF6 proved to be an efficient catalyst that serves as a safe alternative to AgClO4. Scope and limitation is discussed on this new catalyst in the processes including (1) alkyl/alkenyl transfer reaction from organozirconocene chloride to aldehyde, (2) two- and four-carbon homologation of aldehyde, (3) dual synthetic methods of 1,3-dienes from aldehydes/ketones via 1,3-bimetallic species, and (4) three-component alkylative cycloaddition via o-quinodimethane species.

HIGHLY STEREO- AND REGIOSELECTIVE PALLADIUM-CATALIZED SYNTHESES OF (3E,5Z)-(3E,5E)-,AND (3Z,5E)-1,3,5-UNDECATRIENE

(3E,5Z)-1,3,5-Undecatriene (3) having 98.2percent stereoisomeric purity has been prepared by a new and expeditious route involving two selective Pd-catalyzed carbon-carbon bond forming reactions.The key step of this synthesis is a highly diastereoselective Pd-catalyzed cross-coupling reaction between 1-heptynylzinc chloride (11a) and a molar excess of (E)/(Z)-1,2-dibromoethylene (12). Another highly diastereoselective Pd-catalyzed reaction, which involves a cross-coupling between trimethylsilylethynylzinc chloride (15) and molar excesses of stereoisomeric mixtures of 1-bromo-1-alkenes (16), has been used to prepare (E)-1-trimethylsilyl-3-nonen-1-yne (10a), a key intermediate for the synthesis of (3E,5E)- and (3Z,5E)-undecatriene, (4) and (5).Compounds 3 and 4, isolated from the essential oil of Ferula galbaniflua, also occur together with compound 5 in the male attracting oils of seaweeds.These substances have odors highly appreciated in perfumery.