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Usage

Uses

Used in Flavoring and Fragrance Industry:
1-(furan-2-yl)pentan-1-ol is used as a flavoring agent and fragrance in the food and beverage industry for its appealing aroma, enhancing the sensory experience of various products.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, 1-(furan-2-yl)pentan-1-ol is utilized as a key intermediate in the synthesis of various organic compounds and pharmaceuticals, contributing to the development of new drugs and medicinal agents.
Used in Antioxidant and Antimicrobial Applications:
1-(furan-2-yl)pentan-1-ol is studied for its potential antioxidant and antimicrobial properties, making it a compound of interest for applications in medicine and healthcare, where it could be used to improve health outcomes and prevent infections.

Upstream product

• 98-01-1 furfural 
• 693-03-8 n-butyl magnesium bromide 
• 110-00-9 furan 
• 78508-98-2 lithium (2S,3R)-2,3-(N,O-benzylidyne)-2-amino-3-hydroxy-butyrate 
• 109-65-9 1-bromo-butane 
• 103560-62-9 (2E)-4-oxo-2-nonenal 
• 614-99-3 Ethyl 2-furoate 
• 693-04-9 butyl magnesium bromide 
• 109-72-8 n-butyllithium 

Downstream Products

• 14032-66-7 5-hydroxy-2-(5H)-furanone 
• 110-62-3 pentanal 
• 3194-17-0 1-furan-2-yl-pentan-1-one 
• 623-93-8 5-nonanol 
• 13686-96-9 nonane-1,5-diol 
• 4940-17-4 2-butyl-3-hydroxy-4-pyrone 
• 99062-45-0 1-(furan-2-yl)pentan-1-amine 
• 134340-65-1 N-(1-(furan-2-yl)pentyl)-4-methylbenzenesulfonamide 
• 132381-19-2 2-(1-Phenylsulfanyl-pentyl)-tetrahydro-furan 
• 16695-34-4 (E)-4-none-1-ol 
• 37174-92-8 4-oxo-nonanoic acid ethyl ester 

Relevant academic research and scientific papers

Reaction products of γ-tocopherol with (E)-4-oxo-2-nonenal in acidic acetonitrile

γ-Tocopherol was reacted with (E)-4-oxo-2-nonenal (ONE) at 37 °C in an acidic acetonitrile solution. The reaction products were isolated by reversed-phase high-performance liquid chromatography and their structures were characterized to be 5-substituted γ

Manganese=Catalyzed Achmatowicz Rearrangement Using Green Oxidant H2O2

Oxidation reactions have been extensively studied in the context of the transformations of biomass=derived furans. However, in contrast to the vast literature on utilizing the stoichiometric oxidants, such as m=CPBA and NBS, catalytic methods for the oxidative furan=recyclizations remain scarcely investigated. Given this, we report a means of manganese=catalyzed oxidations of furan with low loading, achieving the Achmatowicz rearrangement in the presence of hydrogen peroxide as an environmentally benign oxidant under mild conditions with wide functional group compatibility.

Photooxygenation of azidoalkyl furans: Catalyst-free triazole and new endoperoxide rearrangement

Photooxygenation of azidoalkyl furans has revealed both a novel triazole formation method and a unique endoperoxide rearrangement. The key step of this method is a 3 + 2 cycloaddion of the azide to the endoperoxide intermediate. The reduction of the peroxide bond and two subsequent C-C bond cleavages provide a triazole having a newly formed carboxylic acid functionality. The reactions are clean and efficient with yields ranging from 60% to 90%.

Using water, light, air and spirulina to access a wide variety of polyoxygenated compounds

A new set of completely green methods utilising air, light, water and spirulina to transform readily accessible furan substrates into a diverse range of synthetically useful polyoxygenated motifs commonly found in natural products is presented herein. The Royal Society of Chemistry 2012.

A novel one-pot synthesis of secondary alcohols from esters

Alkylation or vinylation by using organometallic reagents after partial reduction of carboxylic esters with LDBBA gave secondary alcohols, also involving allyl alcohols, without any isolation of intermediates in good yield (54-78%).

Efficient chemoselective addition of grignard reagents to carbonyl compounds in 2-methyltetrahydrofuran

Compared with tetrahydrofuran (THF) as a solvent for the addition reactions between Grignard reagents and carbonyl compounds 2-methyltetrahydrofuran affords the corresponding adducts in higher yields with higher chemoselectivities. Moreover, 2-methyltetrahydrofuran can be readily recycled and reused, which lowers the cost of the process and makes the reaction greener.

Enantioselective addition of tris(TADDOL) organocerium reagents to aldehydes

A significant improvement in enantioselectivity (up to 92% ee) was achieved in butyl additions to a range of aldehydes with a novel tris(TADDOL) organocerium reagent.

Singlet Oxygen Oxidation of Substituted Furans to 5-Hydroxy-2(5H)-furanone

The conditions for the regiospecific singlet oxygen oxidation of various 2,4-disubstituted furans 9 to 4-substituted-2(5H)-furanones 3 are developed.The presence of a C-2 substituent (e.g., trimethylsilyl, tert-butyldimethylsilyl, or tributylstannyl) in 9 is an absolute requirement for the formation of the 4-substituted-5-hydroxy-2(5H)-furanone regioisomer 3.When the C-2 substituent is triethylsilyl (TES) or TBDMS, however, apart from 3, the corresponding 5-trialkylsiloxy derivative 11 is also isolated in a significant amount.These silyl acetals are unexpectedly stable but can be hydrolyzed back to 3 on stirring with dilute acid.The formation of silyl acetals, to our knowledge, has never been reported in the singlet oxygen oxidation of (trialkylsilyl)furan.A plausible mechanism for their formation is proposed.The presence of a catalytic amount of water in the oxidation of 2-(trialkylsilyl)-4-substituted-furans not only eliminates the formation of the silyl acetals but also speeds up the rate of the oxidation process.Moreover, the oxidation can then be carried out at 0 deg C instead of at -78 deg C.Oxidation of 2-(1-hydroxyalkyl)-4-substituted-furans in the absence of a reducing agent gives little or no sign of 2,5-disubstituted-6-hydroxy-3(2H)-pyranone 23 but instead 26 selectively.Thus, the (1-hydroxy)alkyl group can be utilized as the trialkylsilyl or trialkylstannyl group in dictating the regioselectivity in the singlet oxygen oxidation of substituted furans.

Carbon-Carbon Bond-Forming Reactions Using Cerium Metal or Organocerium(III) Reagents

Carbon-carbon bond-forming reactions using cerium metal or organocerium(III) reagents have been investigated.Cerium amalgam is an effective reagent for the chemoselective preparation of homoallylic alcohols from allyl halides and carbonyl compounds.These same reagent can also be satisfactorily employed for the Reformatsky-type reaction of α-halo esters with carbonyl compounds.It has been shown that organocerium(III) reagents are conveniently generated by the reaction of organolithiums with cerium(III)iodide or cerium(III)chloride.The reagents are less basic thanorganolithiums or Grignard reagents, and they react cleanly at -78 to -65 deg C with various carbonyl compounds to afford the addition products in high yields, even though the substrates are susceptible to enolization or metal-halogen exchange with simple organolithiums.The same reagents react also with α,β-unsaturated compounds to yield 1,2-addition products in high selectivity.

Generation and Reactivities of Organocerium Reagents

Organocerium reagents, prepared in situ by the treatment of organolithium compounds with cerium(III) iodide, exhibit characteristic reactivities toward ketones; at -65 deg C, nucleophilic additions give the corresponding tertiary alcohols in excellent yields; while, at 0 deg C to ca. room temperature, reductive coupling and/or reduction of the ketones prevail.