4938-52-7

Usage

Uses

Used in Analytical Chemistry:
1-Hepten-3-ol is used as an analytical standard for the determination of the analyte in various products such as meat products, packaged vegetables, food products, wine, and fruit samples. This is achieved through gas chromatography (GC) based techniques, allowing for accurate identification and quantification of the compound in these samples.
Used in Flavor and Fragrance Industry:
1-Hepten-3-ol, with its unique aroma and taste profile, is used in the flavor and fragrance industry to add a green, sweet, and buttery note to various products. Its high strength odor makes it suitable for use in a diluted form, typically in a 1.00% solution or less.
Used in Food Industry:
In the food industry, 1-Hepten-3-ol is utilized for its characteristic taste and aroma, which can enhance the flavor of various food products. It is reported to be found in banana, beer, patchouli oil, green pepper, and red pepper, contributing to their unique flavor profiles.
Used in Agricultural Industry:
1-Hepten-3-ol may also be used in the agricultural industry, particularly in the cultivation and processing of crops such as green pepper and red pepper, where its presence can contribute to the overall quality and flavor of the produce.

InChI:InChI=1/C7H14O/c1-3-5-6-7(8)4-2/h4,7-8H,2-3,5-6H2,1H3/t7-/m1/s1

Upstream product

• 693-03-8 n-butyl magnesium bromide 
• 107-02-8 acrolein 
• 3739-64-8 allyl n-butyl ether 
• 110-52-1 1,4-dibromo-butane 
• 109-69-3 n-Butyl chloride 
• 1436-34-6 1,2-Epoxyhexane 
• 2181-42-2 trimethylsulphonium iodide 
• 109-72-8 n-butyllithium 
• 110-62-3 pentanal 
• 1826-67-1 vinyl magnesium bromide 
• 119204-45-4 (2S,3S)-1-Benzenesulfonyl-2-trimethylsilanyl-heptan-3-ol 
• 84782-62-7 [((E)-Hept-2-enyl)selanyl]-benzene 
• 24764-98-5 2-bromohexanal 
• 37675-31-3 (E)-1-bromo-3-chloroprop-1-ene 

Downstream Products

• 34686-77-6 1-bromo-2-heptene 
• 4938-52-7 (3R)-1-hepten-3-ol 
• 103404-57-5 1,2,3-heptanetriol 
• 106-35-4 heptan-3-one 
• 64-18-6 formic acid 
• 109-52-4 valeric acid 
• 4938-52-7 (S)-Hept-1-en-3-ol 
• 69361-38-2 ethyl (4E)-non-4-enoate 
• 159617-00-2 1-(2-nitrophenyl)-3-heptanone 
• 122016-54-0 1-Methyl-4-(1-vinyl-pentyloxymethanesulfonyl)-benzene 
• 55682-98-9 (+/-)-3-Chloro-1-heptene 
• 54620-75-6 (1-Vinyl-pentyloxymethyl)-benzene 
• 68703-33-3 (E)-1-chloro-2-heptene 
• 110-62-3 pentanal 

Relevant academic research and scientific papers

A stereospecific synthesis of 2,3-disubstituted tetrahydrofuran derivatives

A stereospecific synthesis of 2,3-difunctionalised tetrahydrofurans via a transmetallation-alkylation sequence of the corresponding 2-(tri-butylstannyl)tetrahydrofurans is described.

Highly Enantioselective Iridium-Catalyzed Coupling Reaction of Vinyl Azides and Racemic Allylic Carbonates

The iridium-catalyzed enantioselective coupling reaction of vinyl azides and allylic electrophiles is presented and provides access to β-chiral carbonyl derivatives. Vinyl azides are used as acetamide enolate or acetonitrile carbanion surrogates, leading to γ,δ-unsaturated β-substituted amides as well as nitriles with excellent enantiomeric excess. These products are readily transformed into chiral N-containing building blocks and pharmaceuticals. A mechanism is proposed to rationalize the chemoselectivity of this coupling reaction.

Asymmetric Synthesis of γ-Secondary Amino Alcohols via a Borrowing-Hydrogen Cascade

The borrowing-hydrogen (or hydrogen autotransfer) process, where the catalyst dehydrogenates a substrate and formally transfers the H atom to an unsaturated intermediate, is an atom-efficient and environmentally benign transformation. Described here is an example of an asymmetric borrowing-hydrogen cascade for the formal anti-Markovnikov hydroamination of allyl alcohols to synthesize optically enriched γ-secondary amino alcohols. By exploiting the Ru-(S)-iPrPyme catalyst with minimal stereogenicity, a cascade process including dehydrogenation, conjugate addition, and asymmetric reduction was developed. The mild conditions, functional group tolerance, and broad substrate scope (54 examples) demonstrate the synthetic practicality of the catalytic system.

Tailoring Interfacial Lewis Acid-Basic Pair on ZnO/4Mg1ZrOx Allows Dehydrogenative α-Methylenation of Alcohols with Methanol to Allylic Alcohols

Allylic alcohols are the essential building blocks widely used in diverse streams of organic inventions for pharmaceuticals, fragrances, agrochemicals and polymers. Currently, allylic alcohols are industrially produced from petroleum-based feedstocks via atom uneconomic processes. More sustainable synthesis route for allylic alcohols is limited. Herein, a methodology for the direct and highly selective production of allylic alcohols has been accomplished by controlled dehydrogenative α-methylenation of alcohols with methanol. This transformation is enabled by interfacial Lewis acid-basic pair on tailor-made ZnO/4Mg1ZrOx mixed oxide. High selectivity (83～92%) of allylic alcohols is the consequence of alcohols acceptorless dehydrogenation to liberation of H2 and Meerwein-Ponndorf-Verley type hydrogen transfer onto C = O bonds of unsaturated aldehydes. Furthermore, the prepared ZnO/4Mg1ZrOx mixed oxide shows good stability after 200 h time on stream test. These observations could additionally allow us to design multifunctional solid acid-basic catalysts for the transformations of renewable oxygenates into value-added chemicals.

Access to Saturated Thiocyano-Containing Azaheterocycles via Selenide-Catalyzed Regio-A nd Stereoselective Thiocyanoaminocyclization of Alkenes

An efficient route for the synthesis of saturated thiocyano-containing azaheterocycles by selenide-catalyzed regio-A nd stereoselective thiocyanoaminocyclization of alkenes is disclosed. The desired products were obtained in moderate to high yields under mild conditions. The generality of this method was elucidated by its efficient application in thiocyano oxycyclization of alkenes.

Visible light-induced diastereoselective semihydrogenation of alkynes to cis-alkenes over an organically modified titanium(IV) oxide photocatalyst having a metal co-catalyst

Hydrogen (H2)-free and poison (lead and quinoline)-free semihydrogenation of alkynes to cis-alkenes under gentle conditions is one of the challenges to be solved. In this study, a titanium(IV) oxide photocatalyst having two functions (visible light responsiveness and semihydrogenation activity) was prepared by modification with 2,3-dihydroxynaphthalene (DHN) and a copper (Cu) co-catalyst, respectively. The photocatalyst (DHN/TiO2-Cu) showed high performance for diastereoselective semihydrogenation of alkynes to cis-alkenes in water-acetonitrile solution under visible light irradiation without the use of H2 and poisons. Alkynes having reducible functional groups were converted to the corresponding alkenes with the functional groups being preserved. The addition of water to acetonitrile changed the amount of alkynes adsorbed on the photocatalyst, which was a decisive factor determining the rate of hydrogenation. A relatively large apparent activation energy, 27 kJ mol?1, was obtained by a kinetic study, indicating that the rate-determining step of this reaction was not an electron production process but a thermal catalytic semihydrogenation process over the Cu co-catalyst. Semihydrogenation and hydrogen evolution occurred competitively on Cu metals and the former became predominant at slightly elevated temperatures, which is discussed on the basis of the kinetic parameters of two reactions.

Stereodivergence in the Ireland-Claisen Rearrangement of α-Alkoxy Esters

A systematic investigation into the Ireland-Claisen rearrangement of α-alkoxy esters is reported. In all cases, the use of KN(SiMe3)2 in toluene gave rearrangement products corresponding to a Z-enolate intermediate with excellent diastereoselectivity, presumably because of chelation control. On the other hand, chelation-controlled enolate formation could be overcome for most substrates through the use of lithium diisopropylamide (LDA) in tetrahydrofuran (THF).

Enantioselective addition of selenosulfonates to α,β-unsaturated ketones

An organo-catalyzed enantioselective addition of selenosulfonates to α,β-unsaturated ketones was developed for the first time. With a chiral squaramide as an efficient catalyst, the desired α-selenylated ketones were obtained in a good yields with high enantioselectivity up to 89% ee, and good results could be obtained on a gram scale. The products could also be efficiently transformed into useful building blocks with a propenylic stereocenter; the strategy presented in this study may find further applications in organic synthesis.

A Re2O7catalyzed cycloetherification of monoallylic diols

A Re2O7catalyzed cycloetherification of monoallylic diols is described. The reaction features short reaction time, mild reaction conditions and exclusive E selectivity. A wide range of monoallylic alcohols with alkyl or aryl substituents on olefin smoothly undergo ring closure to deliver corresponding oxa-heterocycles. The reaction is also operationally simple and not sensitive to air and moisture.

A short and modular approach towards 3,5-disubstituted indolizidine alkaloids

3,5-Dialkyl indolizidines have been prepared in four linear steps from commercially available starting materials. The sequence involves two direct α-functionalization steps and a subsequent reductive amination and provides diastereoselective access to both C-3 epimers of the 5,9-trans-substituted indolizines. The naturally occurring indolizidines 195B and 223AB have been synthesized using this methodology.