90192-96-4

Usage

Uses

Used in Organic Synthesis:
[S,(+)]-4-Heptyne-2-ol is utilized as a reagent in organic synthesis, where its capacity to undergo various chemical reactions makes it a valuable component in creating different compounds.
Used in Pharmaceutical Production:
[S,(+)]-4-Heptyne-2-ol is also employed in the production of pharmaceuticals, where its unique properties can be harnessed to develop new drugs with specific therapeutic effects.
Used in Agrochemicals:
[S,(+)]-4-Heptyne-2-ol finds application in the agrochemical industry, potentially contributing to the development of new pesticides or other agricultural chemicals that can enhance crop protection and yield.
Used in Flavor and Fragrance Industry:
Its utilization extends to the flavor and fragrance sector, where it may be used to create or modify scents and tastes in various consumer products.
Used in Antimicrobial Applications:
[S,(+)]-4-Heptyne-2-ol has been investigated for its potential antibacterial and antifungal properties, suggesting that it could be used in the development of new antimicrobial agents to combat infections.

Upstream product

• 53723-18-5 (+/-)-5-octyn-3-ol 
• 107-00-6 but-1-yne 
• 16088-62-3 (S)-Propylene oxide 

Downstream Products

• 65756-08-3 (S)-(+)-6-Heptyn-2-ol 

Relevant academic research and scientific papers

Synthesis and biological evaluation of 12-, 13-, 14-membered macrolides and open chain 2,6-trans-disubstituted dihydropyran analogues for aspergillides

Stereoselective synthesis of twenty (three 12-, five 13- and twelve 14-membered) macrolides and seventeen functionalized 2,6-trans-disubstituted dihydropyran derivatives have been achieved. The key reactions include an Achmatowicz rearrangement, Ferrier-type alkynylation, Yamaguchi macrolactonization and Lindlar's hydrogenation. Biological screening of the synthesised compounds showed moderate activity against human cancer cell-lines.

Total Synthesis of Chaetoglobin A via Catalytic, Atroposelective Oxidative Phenol Coupling

The first total synthesis of chaetoglobin A (1), which features a chiral axis between two identical highly oxygenated bicyclic cores, was successfully completed in 12 steps from 2,6-dimethoxytoluene. Vanadium-catalyzed oxidative phenol coupling, as a key

Total synthesis of (+)-brefeldin a

(+)-Brefeldin A was synthesized through an efficient route, which features (1) construction of the five-membered ring from a Crimmins aldol via tandem Li-I exchange and carbanion-mediated cyclization with concurrent removal of the chiral auxiliary, (2) introduction of the lower side chain (C10 to C16) via a Rh-catalyzed Michael addition of a vinyl boronic acid, (3) stereoselective reduction of the C7 ketone with Sml2, and (4) a 2-methyl-6- nitrobenzoic anhydride-mediated (Shiina) lactonization.

Enantioselective esterifications of unsaturated alcohols mediated by a lipase prepared from Pseudomonas sp.

Competition experiments and measurements of enantioselectivities were used to develop a simple active-site model (Figure 1) for resolutions of β-hydroxy-α-methylene carbonyl compounds III via acyl transfers mediated by lipase from Pseudomonas sp. (AK). Further experiments were used to test and refine this model with respect to resolutions of allylic, propargylic, homopropargylic, and other alcohols (Tables I-IV, respectively). The model proved extremely reliable for predicting the sense of the asymmetric induction, and the combined data collected in this paper give an indication of what structural features of the substrates can be correlated with high enantioselectivities in these resolutions. Furthermore, the results account for the conspicuous reversal of enantioselectivity previously observed in resolutions of γ-hydroxy-α,β-unsaturated esters 35. Kinetic resolutions of two substrates (allenol 14 and dienol 9) via asymmetric epoxidations were performed for comparison with the methodology presented in this paper.

Facile synthesis of (+)-Brefeldin A

(+)-Brefeldin A (1) was synthesized by using (+)-4-cyanomethylcyclopent-2-en-1-one (2) as a key compound. 4-Hydroxy-2-enoate functionality was built by the reaction of the aldehyde (7) with (S)-ethyl p-chlorophenylsulfinylacetate.

Synthesis of Z,Z-Skipped Diene Macrolide Pheromones for Cryptolestes and Oryzaephilus Grain Beetles (Coleoptera Cucujidae)

Three macrolide aggregation pheromones for Cryptolestes pusillus, Cryptolestes turcicus, and Oryzaephilus mercator were synthesized stereoselectively from acyclic precursors.The first, 13-methyl-(5Z,8Z)-tridecadienolide (I), is an aggregation pheromone for C. turcicus and had been tentatively identified previously in Phoracantha synonyma.The second, 11-methyl-(3Z,6Z)-undecadienolide (II), is an aggregation pheromone for O. mercator.The third, (3Z,6Z)-dodecadienolide (III) is an aggregation pheromone for O. mercator and is also slightly attractive to C. pusillus.The racemic and enantiomeric forms of I were synthesized.