68274-97-5

Usage

Uses

Used in Fine Chemicals Industry:
5-Decyn-1-ol is used as a key intermediate in the synthesis of multi-substituted cyclopropanes, which are valuable compounds in the fine chemicals industry. Its presence in these reactions allows for the creation of complex molecular structures with potential applications in pharmaceuticals, agrochemicals, and other specialty chemical products.
Used in Electroplating Industry:
In the electroplating industry, 5-Decyn-1-ol is utilized as a component in the formulation of electroplating solutions. Its unique chemical properties contribute to the enhancement of the plating process, improving the quality and durability of the metal coatings applied to various substrates.
Used in Perfumery Industry:
5-Decyn-1-ol is also employed in the perfumery industry, where it serves as a raw material for the production of fragrances and scented compounds. Its distinctive chemical structure allows it to contribute to the creation of unique and complex aromas, adding depth and character to perfumes and other scented products.

InChI:InChI=1/C10H18O/c1-2-3-4-5-6-7-8-9-10-11/h11H,2-4,7-10H2,1H3

Upstream product

• 42049-41-2 1-iodo-5-decyne 
• 4117-14-0 2-decyn-1-ol 
• 82511-32-8 dec-1-en-5-yne 
• 61898-56-4 (S)-4-methyltetrahydro-2H-pyran-2-one 
• 109-72-8 n-butyllithium 
• 1352757-62-0 C₇H₁₀Cl₂O 
• 108864-78-4 (S)-5-Hydroxy-3-methyl-pentanoic acid 
• 626-51-7 3-methyl glutaric acid 
• 63473-60-9 (R)-3-methylpentanedioic acid monomethyl ester 
• 19013-37-7 dimethyl 3-methylglutarate 
• 100419-71-4 oct-3-ynyl 4-methylbenzenesulfonate 
• 17689-03-1 1-hexynyllithium 
• 14916-80-4 oct-3-yn-1-ol 
• 928-90-5 5-hexyl-1-ol 

Downstream Products

• 51721-39-2 3-decyn-1-ol 
• 4117-14-0 2-decyn-1-ol 
• 69222-06-6 4-decyne-1-ol 
• 69222-07-7 dec-6-yn-1-ol 
• 69222-08-8 7-decyn-1-ol 
• 17643-36-6 9-decyn-1-ol 
• 51652-47-2 (Z)-dec-5-en-1-ol 
• 56578-18-8 (E)-5-decen-1-ol 
• 1205551-40-1 C₁₇H₂₅N 
• 1310564-00-1 C₁₇H₂₅NO₂S 
• 1310563-85-9 1-benzyl-2-pentylpiperidine-2-carbonitrile 
• 1310564-02-3 1-tosyl-2-pentylpiperidine-2-carbonitrile 
• 1310563-91-7 1-benzyl-2-pentyl-2-(trifluoromethyl)piperidine 
• 1310563-92-8 2-pentyl-1-phenyl-2-(trifluoromethyl)piperidine 

Relevant academic research and scientific papers

Method for synthesizing sex pheromone of anarsia lineatella

The invention belongs to the technical field of green pesticide synthesis, and discloses a novel method for synthesizing sex pheromone of anarsia lineatella. The method comprises the following steps:with 5-hexyn-1-ol as a raw material, subjecting 5-hexyn-1-ol and1-bromobutane to a nucleophilic substitution reaction in the presence of n-butyllithium and HMPA to generate 5-decyn-1-ol, then performing reduction via lithium aluminum hydride to obtain (E)-5-decen-1-ol, and finally performing an acetylation reaction to obtain (E)-5-decen-1-ol acetate. According to the invention, a triple bond of alkyne is reduced into an E-type double bond by lithium aluminum hydride, so the method has the advantages of simple synthetic route, mild reaction conditions, good environmental compatibility and the like.

Synthesis of Tetrasubstituted Alkenes by Tandem Metallacycle Formation/Cross-Electrophile Coupling

Nickel-catalyzed cross-electrophile couplings have recently emerged as highly effective and practical methods for the formation of C-C bonds. By merging this process with well-established π-π coupling chemistry, a new method for the synthesis of tetrasubstituted alkenes has been developed. The procedure relies on the use of chlorosilanes as a means of generating reactive vinylnickel intermediates, which are capable of undergoing a reductive cross-electrophile coupling with alkyl halides. The method not only generates highly substituted allylic alcohol derivatives but also obviates the need for stoichiometric organometallic nucleophiles and provides greatly improved scope and functional group tolerance compared with previously developed methods.

A new method for the preparation of non-terminal alkynes: Application to the total syntheses of tulearin A and C

Lactones are known to react with the reagent generated in situ from CCl4 and PPh3 in a Wittig-type fashion to give gem-dichloro-olefin derivatives. Such compounds are now shown to undergo reductive alkylation on treatment with organolithium reagents RLi to furnish acetylene derivatives bearing the substituent R at their termini (R=Me, n-, sec-, tert-alkyl, silyl); the reaction can be catalyzed with either Cu(acac)2 or Fe(acac)3/1,2-diaminobenzene. Two alkynol derivatives prepared in this way from readily accessible lactone precursors served as the key building blocks for the total syntheses of the cytotoxic marine macrolides tulearin A (1) and C (2). The assembly of these fragile targets hinged upon ring closing alkyne metathesis (RCAM) followed by a formal trans-reduction of the resulting cycloalkynes via trans-hydrosilylation/protodesilylation.

Synthesis of heneicos-6(Z)-en-11-one, dec-5(Z)-en-l-yl acetate, dec-5(Z)-En-1-y1-3-methylbutanoate (insect sex pheromones)

Synthesis of heneicos-6(Z)-en-11-one 1, dec-5(Z)-en-l-yl acetate 2, dec-5(Z)-en-l-yl-3-methylbutanoate 3 has been accomplished by utilizing sodium acetoxyborohydride generated in situ from sodium borohydride and acetic acid as the key step for selective hydroboration-iodination/oxidation.

Deprotection of benzyl ethers using 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) under photoirradiation

The deprotection of benzyl ethers was effectively realized in the presence of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) in MeCN under photoirradiation using a long wavelength UV light.

Chemistry of natural compounds and bioorganic chemistry a convergent synthesis of octadeca-2E,13Z-dienyl acetate, a pheromone component of Synanthedon tipuliformis C

A convergent synthesis of octadeca-2E,13Z-dienyl acetate, a pheromone component of Synanthedon tipuliformis C., has been developed. The synthesis is based on cross-coupling of 8-iodooct-2E-en-1-ol THP ether with dec-57-enyl bromide catalyzed by CuBr.

A Tandem Synthesis of (+/-)-Euphococcinine and (+/-)-Adaline

Intramolecular hydroxylamine-alkyne cyclisation of the hydroxylamines 8 and 9 afforded six-membered cyclic nitrones which without isolation underwent a tandem intramolecular dipolar cycloaddition to produce the tricyclic isoxazolidines 6 and 7 respectively.These were converted in two steps into the ladybird defence alkaloids (+/-)-euphococcinine 4 and (+/-)-adaline 5.

Electrochemical Reduction and Intramolecular Cyclization of 1-Iodo-5-decyne and 1-Bromo-5-decyne at Vitreous Carbon Cathodes in Dimethylformamide

In dimethylformamide containing tetramethylammonium perchlorate, cyclic voltammograms for reduction of 1-iodo-5-decyne and 1-bromo-5-decyne at a vitreous carbon electrode each consist of a single irreversible wave due to two-electron scission of the carbon-halogen bond.Preparative-scale electrolyses of 1-iodo-5-decyne yield pentylidenecyclopentane, 5-decyne, 1-decen-5-yne, and a small amount of 5-decyn-1-ol, whereas reduction of 1-bromo-5-decyne affords mainly 5-decyne and 1-decen-5-yne along with a modest quantity of pentylidenecyclopentane.Differences in product distributions correlate with the extent to which the 5-decyn-1-yl radical persists as a transient species.Pentylidenecyclopentane arises via intramolecular cyclization of the 5-decyn-1-yl radical followed by hydrogen atom abstraction, 5-decyne is formed via protonation of the 5-decyn-1-yl carbanion by either water or the tetramethylammonium cation, and 1-decen-5-yne and 5-decyn-1-ol are obtained, respectively, via E2 and SN2 reactions between unreduced starting material and hydroxide ion (generated by deprotonation of water).In the presence of a proton donor (diethyl malonate or hexafluoroisopropyl alcohol), the quantities of pentylidenecyclopentane and 5-decyne rise noticeably and the yield of 1-decen-5-yne falls dramatically.

INSECT PHEROMONES AND THEIR ANALOGS. XII. SYNTHESIS OF THE ISOMERIC DEC-5-ENYL ACETATES - THE SEX PHEROMONES OF Anarsia lineatella AND Agrotis segetum

A new route for the synthesis of dec-5E- and -5Z-enyl acetates - the sex pheromones of the peach-tree borer and of the turnip moth - is proposed which is based on the two-stage hydroxyethylation of hex-1-yne using 2-chloroethyl vinyl ethers and ethylene oxide.