77657-78-4

Usage

Uses

Used in Fragrance and Flavor Industry:
(2Z,4E)-undeca-2,4-dien-1-ol is used as a key ingredient in the production of fragrances and flavors due to its pleasant, floral scent. It adds a unique aroma to various products, enhancing their appeal to consumers.
Used in Organic Synthesis:
(2Z,4E)-undeca-2,4-dien-1-ol serves as a precursor in the synthesis of other organic compounds. Its unique structure allows for further chemical reactions, making it a valuable building block in the creation of new molecules with diverse applications.
Used in Biomedicine:
(2Z,4E)-undeca-2,4-dien-1-ol has potential applications in the field of biomedicine due to its antimicrobial and antifungal properties. It can be utilized in the development of new treatments and therapies to combat infections and improve overall health.

Upstream product

• 82994-41-0 (E)-3-(tri-n-butylstannyl)-2-propen-1-ol 
• 52356-93-1 (Z)-1-octenyl iodide 
• 73303-09-0 lithium di(n-hexyl)cuprate 
• 107-19-7 propargyl alcohol 
• 629-05-0 n-octyne 
• 107-18-6 allyl alcohol 
• 55976-14-2 (Z)-1,4-undecadiene 
• 31508-11-9 undeca-1-en-4-yne 

Relevant academic research and scientific papers

Ligand effects on the stereochemistry of Stille couplings, as manifested in reactions of Z-alkenyl halides

Unexpected losses in stereochemistry from Stille reactions involving Z-alkenyl halides have been shown to be ligand dependent. A new set of reaction conditions has been developed that, in most cases, leads to highly stereoselective cross-couplings under mild conditions, along with improved yields.

Highly selective synthesis of conjugated dienoic and trienoic esters via alkyne elementometalation - Pd-catalyzed cross-coupling

All four stereoisomers (7-10) of ethyl undeca-2,4-dienoate were prepared in ≥98% isomeric purity by Pd-catalyzed alkenylation (Negishi coupling) using ethyl (E)- and (Z)-β-bromoacrylates. Although the stereoisomeric purity of the 2Z,4E-isomer (8) prepared by Suzuki coupling using conventional alkoxide and carbonate bases was ≤95%, as reported earlier, the use of CsF or nBu4NF as a promoter base has now been found to give all of 7-10 in ≥98% selectivity. Other widely known methods reveal considerable limitations. Heck alkenylation was satisfactory for the syntheses of the 2E,4E and 2E,4Z isomers of ≥98% purity, but the purity of the 2Z,4E isomer was ≤95%. Mutually complementary Horner-Wadsworth-Emmons and Still-Gennari (SG) olefinations are also of considerably limited scopes. Neither 2E,4Z nor 2Z,4Z isomer is readily prepared in ≥90% selectivity. In addition to (2Z,4E)-dienoic esters, some (2Z,4E,6E)- and (2Z,4E,6Z)-trienoic esters have been prepared in ≥98% selectivity by a newly devised Pd-catalyzed alkenylation-SG olefination tandem process. As models for conjugated higher oligoenoic esters, all eight stereoisomers for ethyl trideca-2,4,6-trienoate (23-30) have been prepared in ≥98% overall selectivity.

Palladium-catalysed Reaction of Vinylic Halides with Allylic Alcohols: A Highly Chemo-, Regio- and Stereo-controlled Synthesis of Conjugated Dienols

A new, direct, highly chemo-, regio- and stereo-controlled method for the construction of (E,E) and (E,Z) conjugated dienols from vinylic halides and allylic alcohols is described.

Structural Dynamics of Pentadienyl Metal-Compounds Bearing a Terminal Alkyl Substituent: Both 'Stereoselective' and 'Stereodefensive' Synthesis of a Natural Perfume

The (2Z,4E)-, (2E,4Z)- and (2E,4E)-isomers of 2,4-decandien-1-ol (5) have been obtained with high and predictable stereochemical homogeneity starting from both (Z)- and (E)-1,4-decadiene.These hydrocarbons were hydroxylated in a reaction sequence consisting of metallation (by means of s-butyllithium or butyllithium/potassium-t-butoxide, giving rise to organometallic intermediates of specific conformations), dimethoxyborylation and oxidation.The different decadienols as well as (2E,4Z)-2,4-undecadien-1-ol were converted into the isovalerates, the ester derived from (2E,4Z)-2,4-decadien-1-ol being a natural flavor component.