103197-98-4

Usage

Uses

Used in Pharmaceutical Industry:
(5E)-Hept-5-en-3-yn-1-ol is used as a synthetic intermediate for the development of pharmaceutical compounds. Its unique structure with both alkene and alkyne functional groups allows for versatile chemical reactions, facilitating the synthesis of a wide range of bioactive molecules.
Used in Fragrance Production:
(5E)-Hept-5-en-3-yn-1-ol is used as a component in the production of fragrances. Its specific chemical structure contributes to the creation of unique scents, making it a valuable ingredient in the formulation of various fragrances.
Used in Flavoring Agents:
(5E)-Hept-5-en-3-yn-1-ol is also utilized in the production of flavoring agents. Its chemical properties allow it to impart distinct tastes and flavors to food and beverage products, enhancing their overall sensory appeal.

Upstream product

• 4447-21-6 Ethylbiacetylen 
• 5073-11-0 (E)-5-(tetrahydropyran-2-yloxy)pent-3-en-1-yne 
• 35042-52-5 (E)-2-penten-4-yn-1-ol 
• 107-00-6 but-1-yne 
• 106-89-8 epichlorohydrin 
• 120569-51-9 hepta-2,4-diyn-1-ol 
• 54664-99-2 1-hepten-4-yn-3-ol 
• 37428-55-0 (E)-3-bromoprop-2-en-1-ol 

Downstream Products

• 33580-05-1 1,3-trans,5-cis-octatriene 
• 54364-62-4 (7E,9Z)-7,9-dodecadien-1-yl acetate 
• 70979-88-3 (2E,4Z)-hepta-2,4-dien-1-ol 

Relevant academic research and scientific papers

1H and 13C NMR spectra and one-bond 13C,13C coupling constants of (E)-2-alken-4-yn-1-ols, (E)-2-alken-4-yn-1-yl acetates and (E)-2-alken-4-yn-1-als

13C and some selected 1H NMR chemical shifts of conjugated (E)-enynes of the type of (E)-2-alken-4-yn-1-ols (RC≡CCH=CHCH2OH; R=H, Me, Et, n-Pr, n-Bu, SiMe3), (E)-2-alken-4-yn-1-yl acetates (RC≡CCH=CHCH2OAc; R=H, Me, Et, n-Pr, n-Bu) and (E)-2-alken-4-yn-1-als (RC≡CCH=CHCH=O; R=Et, n-Pr) and of (2Z,4E)-deca-2,4-dien-6-yne as a conjugated (Z,E)-dienyne were measured. The unequivocal assignment of the 13C NMR chemical shifts is based on the application of standard techniques such as H,H-COSY, C,H-COSY and APT and, above all, on the investigation of the C,C connectivities by determination of the one-bond 13C,13C coupling constants 1Jc.c. These coupling constants show typical values for the different structural fragments. The effect of increments of the alkyl group on the resonances of the acetylenic carbon atoms are compared with those of the n-alkynes. The shift effects observed on going from (E)-2-alken-4-yn-1-ols to (E)-2-alken-4-yn-1-als are discussed in comparison with results from other classes of compounds.

Synthesis of 7E,9Z-dodecadienyl acetate, the sex pheromone of Lobesia botrana Shiff

Two syntheses of 7E,9Z-dodecadienyl acetate from 1,3-butadiyne were carried out using either 2E,4Z-heptadienyl acetate or 1-bromo-3E,5Z-octadiene as the key intermediates.The latter underwent organocopper cross-coupling with the respective complementary Grignard reagents (prepared from the corresponding 1-tert-butoxy-ω-chlorohydrins) as alkylating agents.

A comparative study of the synthetic paths from 1-butyne to 2E,4Z-heptadien-1-ol

2E,4Z-Heptadien-1-ol (1), the key intermediate in the synthesis of the grapevine moth sex pheromone, was obtained from 1-butyne by a number of alternative procedures, including various variants of the stereocontrolled building of the conjugated E,Z-diene system (Cadiot-Chodkiewicz cross-coupling, alkyne-vinyl halide cross-coupling catalyzed by palladium complexes, anionotropic allylic rearrangement, partial cis- and trans-reduction of the triple bond).None of them could provide for configurational uniformity of 1.The most acceptable path to obtain 1 in multigram amounts appears to be that which proceeds via the conjugated diynol and enynol intermediates with subsequent catalytic cis-hydrogenation.