62992-46-5

Basic information

• Product Name: 2-(4-PENTYNYLOXY)TETRAHYDRO-2H-PYRAN 9&
• Synonyms: 2-(Pent-4-yn-1-yloxy)tetrahydro-2H-pyran;2-(Pent-4-ynyloxy)tetrahydro-2H-pyran;Tetrahydro-2-(4-pentyn-1-yloxy)-2H-Pyran;2-(4-Pentynyloxy)tetrahydro-2H-pyran 97%;2-(4-PENTYNYLOXY)TETRAHYDRO-2H-PYRAN 9&;2-pent-4-ynoxyoxane
• CAS NO: 62992-46-5
• Molecular Formula: C₁₀H₁₆O₂
• Molecular Weight: 168.23284
• Product Categories: API intermediates;Building Blocks;Heterocyclic Building Blocks;Pyrans;Building Blocks;Chemical Synthesis;Heterocyclic Building Blocks
• Mol File: 62992-46-5.mol

Chemical Properties

• Melting Point: 84-88 °C(lit.)
• Boiling Point: 40-45 °C0.03 mm Hg(lit.)
• Flash Point: 177 °C
• Appearance: /
• Density: 0.968 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.048mmHg at 25°C
• Refractive Index: n20/D 1.4570(lit.)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 2-(4-PENTYNYLOXY)TETRAHYDRO-2H-PYRAN 9&(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-PENTYNYLOXY)TETRAHYDRO-2H-PYRAN 9&(62992-46-5)
• EPA Substance Registry System: 2-(4-PENTYNYLOXY)TETRAHYDRO-2H-PYRAN 9&(62992-46-5)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• Hazardous Substances Data: 62992-46-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
2-(4-Pentynyloxy)tetrahydro-2H-pyran 9& is used as a key reagent in the synthesis of (+)-Citrafungin A, an alkyl citrate compound with significant biological activity. (+)-Citrafungin A acts as a geranylgeranyltransferase (GGTase) inhibitor, which is an enzyme involved in the post-translational modification of proteins. This inhibition can lead to the disruption of essential cellular processes, making it a potential target for the development of antifungal agents.
Additionally, (+)-Citrafungin A exhibits antifungal properties, making it a promising candidate for the treatment of various fungal infections. The use of 2-(4-Pentynyloxy)tetrahydro-2H-pyran 9& in the synthesis of this compound highlights its importance in the development of novel antifungal drugs.
Used in Chemical Research:
2-(4-Pentynyloxy)tetrahydro-2H-pyran 9& is also utilized in chemical research as a versatile building block for the synthesis of various organic compounds. Its unique structure allows it to participate in a wide range of chemical reactions, including addition, substitution, and rearrangement reactions. This makes it a valuable tool for chemists working on the development of new molecules with potential applications in various fields, such as pharmaceuticals, materials science, and agrochemistry.

InChI:InChI=1/C10H16O2/c1-2-3-5-8-11-10-7-4-6-9-12-10/h1,10H,3-9H2

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 5390-04-5 pent-1-yn-5-ol 
• 42330-88-1 1-chloro-3-(2-tetrahydropyranyloxy)propane 
• 1216963-74-4 lithium acetylide-ethylenediamine complex 
• 33821-94-2 3-(tetrahydro-2H-pyran-2-yloxy)propyl bromide 
• 1066-54-2 trimethylsilylacetylene 
• 74-86-2 acetylene 
• 72039-61-3 trimethyl[5-[(tetrahydro-2H-pyran-2-yl)oxy]pent-1-ynyl]silane 
• 97-99-4 Tetrahydrofurfuryl alcohol 
• 3003-84-7 Tetrahydrofurfuryl chloride 
• 59287-66-0 4,5-dibromo-1-pentanol 
• 142-68-7 TETRAHYDROPYRANE 

Downstream Products

• 21890-96-0 7-(tetrahydro-2H-pyran-2-yloxy)hept-3-yn-1-ol 
• 75347-53-4 2,5-dichloro-3-(5-hydroxy-1-pentynyl)-6-methyl-1,4-benzoquinone 
• 928-93-8 4-hexyn-1-ol 
• 57981-61-0 (4E,7Z)-4,7-Tridecadien-1-ol 
• 202405-21-8 (6RS,13R)-6-hydroxy-13-benzyloxy-1-tetrahydropyranyloxytetradec-4-yne 
• 256510-14-2 O-tetrahydropyranyl-5-(3,5-dimethoxyphenyl)-4-pentyn-1-ol 
• 256510-58-4 O-(2-tetrahydropyranyl)-6-(3,5-dimethoxyphenyl)-4-hexyn-1-ol 
• 473542-79-9 2-(10-benzyloxydec-4-yn-1-yloxy)tetrahydropyran 
• 5390-04-5 pent-1-yn-5-ol 
• 622842-71-1 2-[5-(tetrahydropyran-2-yloxy)pent-1-ynyl]benzyl alcohol 
• 853929-20-1 (2S)-1-(benzyloxy)-8-((tetrahydro-2H-pyran-2-yl)oxy)oct-4-yn-2-ol 
• 198411-11-9 5-dimethylphenylsilyl-1-(2-tetrahydropyranyloxy)-4-pentyne 
• 198411-14-2 5-(p-methoxyphenyl)dimethylsilyl-1-(2-tetrahydropyranyloxy)-4-pentyne 
• 198411-13-1 5-dimethyl(p-methylphenyl)silyl-1-(2-tetrahydropyranyloxy)-4-pentyne 

Relevant articles and documents

Syntheses and stereochemical assignment of toxic C17-polyacetylenic alcohols, virols A, B, and C, isolated from water hemlock (Cicuta virosa)

In the course of our study on neurotoxic C17-polyacetylenic alcohols of the toxic plant, Cicuta virosa, virols A (1), B (2), and C (3) were synthesized by stereoselective routes to confirm their stereochemistry and to obtain supply of these compounds for pharmacological study. The syntheses used chiral 3-hydroxy-1-alkyne building blocks, Pd(0)CuI(I)-catalyzed coupling of acetylene with vinyl chloride, and heterocoupling reaction of acetylene mediated by CuI. As a result, the absolute configuration of the stereogenic center of virols A (1), B (2), and C (3) was confirmed as S, S, and S, respectively.

Total synthesis of the antimicrobial fatty acid (5Z,9Z)-14-methylpentadeca-5,9-dienoic acid and its longer-chain analog (5Z,9Z)-24-methylpentacosa-5,9-dienoic acid

The antimicrobial marine fatty acid (5Z,9Z)-14-methylpentadeca-5,9-dienoic acid, recently identified in the phospholipids of the Caribbean gorgonian Eunicea succinea, and its longer-chain analog (5Z,9Z)-24-methylpentacosa-5,9-dienoic acid, initially identified in the phospholipids of the sponge Petrosia ficiformis, have been synthesized for the first time through a common synthetic route. A combination of alkyne-bromide coupling and Wittig reaction resulted in the best combination for assembling the Δ5,9 functionality in high yield and stereoselectivity.

Use of Imidazo[1,5-a]pyridin-3-ylidene as a Platform for Metal-Imidazole Cooperative Catalysis: Silver-Catalyzed Cyclization of Alkyne-Tethered Carboxylic Acids

Silver complexes with 5-(4-(tert-butyl)-1H-imidazol-1-yl)-imidazo[1,5-a]pyridin-3-ylidene ligands were synthesized as metal-imidazole acid-base cooperative catalysts. Single crystal XRD analysis revealed that the silver atom was located in the vicinity of

Stereospecific synthesis of (4e,10z)-4,10-tetradecadienyl acetate, the major sex pheromone of apple leaf miner moth, phyllonorycter ringoniella

The main component of the sex pheromone of many lepidopteran pests, (4E,10Z)-4,10-tetradecadienyl acetate (1) has been synthesized stereoselectively by using a simple route with 4-pentynol as a starting material. The stereoselective formation of the 4E double bond is based on the stereospecific reduction of internal alkyne with lithium aluminium hydride (LAH) while Wittig reaction was used to achieve 10Z double bond in the target pheromone component. The GC purity of the final acetate was achieved 97.87% while isomeric purities are more than 99%. The green chemistry principle shows a new concept towards the multistep pheromone synthesis via green metrics calculations.

Synthesis method of caproic acid-D7

The invention provides a synthesis method of caproic acid-D7, which comprises the following steps of: 1) under the protection of N2, preparing a compound 2 from a compound 1 and DHP in the presence ofdextral camphorsulfonic acid, 2) performing substitution reaction on the compound 2 and deuterated methyl iodide in the presence of n-butyllithium to obtain a compound 3, 3) under the protection of N2, dissolving the compound 3 in methanol, and in the presence of p-toluenesulfonic acid monohydrate, preparing a compound 4, 4) carrying out reduction reaction on the compound 4 in methanol in the presence of 10wt% palladium on carbon and in a deuterium atmosphere to obtain a compound 5, and 5) carrying out oxidation reaction on the compound 5, TEMPO and Aliquat 336 in the presence of potassium bromide and sodium hypochlorite to prepare a compound 6, namely caproic acid-D7. According to the synthesis method disclosed by the invention, highly toxic products such as potassium cyanide are prevented from being used, and the reaction operation is relatively simple and controllable.

Site-Selective trans-Hydrostannation of 1,3- and 1,n-Diynes: Application to the Total Synthesis of Typhonosides E and F, and a Fluorinated Cerebroside Analogue

Propargyl alcohols are privileged substrates for stereochemically unorthodox trans-hydrostannation reactions catalyzed by [Cp*RuCl]4 (Cp=pentamethylcyclopentadienyl), because an incipient hydrogen bond between the -OH group and the polarized [Ru-Cl] unit assists substrate binding. For this very reason, it is also possible to subject diyne derivatives carrying one -OH group to site-selective stannylation, even if the acetylene units are conjugated and hence, electronically coupled. An unusual temperature dependence was observed in that heating tends to improve site-selectivity, whereas per-stannylation is favored when the reaction is carried out in the cold. This counterintuitive trend can be rationalized based on spectroscopic data; additional support comes from the isolation of the unusual bimetallic complex 11. The bridging fulvene and enynyl ligands in 11 are thought to reflect an interligand redox isomerization process likely triggered by synchronous activation of the 1,3-diyne substrate by two metal centers. The preparative relevance of site-selective trans-hydrostannation is illustrated by the total synthesis of two members of the typhonoside series of glycolipids, which are endowed with neuroprotective properties. Moreover, the preparation of a fluoroalkene sphingosine analogue shows that the tin residue also serves as a versatile handle for late-stage modification of a bioactive target compound.

Synthesis method for conopomorpha sinensis bradley sex pheromone compound

The invention discloses a synthesis method for a conopomorpha sinensis bradley sex pheromone compound. The synthesis method comprises the following steps: taking 4-pentyne-1-alcohol as a starting rawmaterial, protecting hydroxyl with 3,4-dihydropyran to obtain a compound 5 protected by THP on the hydroxyl, enabling the compound 5 to generate coupled reaction with trans-dichloroethylene under co-catalysis of a metal palladium compound and cuprous iodide to obtain a compound 6; under catalysis of a metal iron compound, enabling the compound 6 to generate further coupled reaction with bromo cis-3-nonene Grignard reagent to obtain a compound 7; removing a THP protective group of the compound 7 under catalysis of toluenesulfonic acid monohydrate to form a compound 8; reducing the compound 8 toprepare (4E,6E,10Z)-hexadecatriene alcohol, and enabling the (4E,6E,10Z)-hexadecatriene alcohol to generate esterification reaction to obtain (4E,6E,10Z)-hexadecatriene acetate. The synthesis raw materials are simple and easily available, are low in cost, and the synthesis steps are short; and meanwhile, stereoselectivity is high, the yield is obviously increased, and the post-treatment is simpleand convenient.

Structural diversification of the aminobicyclo[4.3.0]nonane skeleton using alkynylsilyl-derived allylic trichloroacetimidates

The amino substituted bicyclo[4.3.0]nonane is a molecular scaffold found in a wide range of natural products and medicinal agents. Despite this, synthetic methods for the general preparation of this structural motif are sparse. Here we evaluate a diastere

METHOD FOR PRODUCING EUSHEARILIDES

Provided are: eushearilides; a method for producing eushearilides; a production intermediate; and a pharmaceutical composition containing eushearilides. By having the Wittig reaction process, Mukaiyama Aldol reaction process and Macrolactonizaion process serve as key processes, eushearilides represented by formula (I) are efficiently produced.

A Gold(I)-Catalyzed Oxidative Rearrangement of Heterocycle-Derived 1,3-Enynes Provides an Efficient and Selective Route to Divinyl Ketones

The gold-catalyzed oxidation of N-tosyl-protected 6-alkynyl-3,4-dihydro-2H-pyridines was studied in detail to obtain divinyl ketones in which one of the double bonds is embedded in a heterocyclic framework. The best reaction conditions were then extended