3857-14-5

Upstream product

• 52426-83-2 2-vinyltetrahydro-2H-pyran 
• 76928-53-5 (+/-)-2-cyanoterahydropyran 
• 171557-95-2 Toluene-4-sulfonic acid 1-ethyl-pent-4-enyl ester 
• 19781-77-2 hept-6-en-3-ol 
• 171557-64-5 N-(6-Heptenyl-3-oxy)pyridine-2(1H)-thione 
• 5631-95-8 2,3-dichlorotetrahydro-2H-pyran 
• 74-96-4 ethyl bromide 
• 110-87-2 3,4-dihydro-2H-pyran 
• 67-56-1 methanol 

Downstream Products

• 1622-10-2 1,5-dibromoheptane 

Relevant academic research and scientific papers

Catalytic synthesis of oxygenate from alcohol

The present invention discloses a method for catalytic synthesis of oxygenate from alcohol. At first, a feeding material comprising at least one alcohol is provided. Next, a copper-containing catalyst is provided and the catalyst further comprises at least one metal element selected from the group consisting of the following: zinc, magnesium, and aluminum elements. Following that, a catalytic reaction of the feeding material over the copper-containing catalyst is carried out to synthesize at least one oxygenate.

Ring closure reactions of substituted 4-pentenyl-1-oxy radicals. The stereoselective synthesis of functionalized disubstituted tetrahydrofurans

N-(Alkyloxy)pyridine-2(1H)-thiones 3 and benzenesulfenic acid O-esters 5 have been synthesized from substituted 4-pentenols 1 or the derived tosylates. Compounds 3 and 5 are efficient sources of free alkoxy radicals 6 which undergo synthetically useful fast ring closure reactions 6 → 8 [k(exo) = (2 ± 1) x 108 s-1 to (6 ± 2) x 109 s-1 (T = 30 ± 0.2°C)]. Tetrahydrofurfuryl radicals 8 can be trapped with, e.g., hydrogen or chlorine atom donors to afford either trans- or cis-disubstituted tetrahydrofurans 10 or 12 depending on the substitution pattern of the 4-pentenyloxy radical. Substituted tetrahydropyrans 11 or 13 are formed in the minor 6-endo-trig cyclization. According to the data of competition kinetics, the observed stereoselectivities in free alkoxy radical cyclizations arise from steric interactions between the substituents in the transition state of the ring closure reactions. Alkyl substituents cause small differences in the measured relative rate constants of 5-exo cyclizations which are reminiscent of the data obtained from the rearrangements of alkyl-substituted 5-hexenyl radicals. Likewise, a stereochemical model for oxygen radical cyclization is proposed where the pentenyloxy chain adopts a six-membered, chairlike transition state with the alkyl substituents preferentially situated in the pseudoequatorial positions leading to 2,5-trans-, 2,4-cis-, and 2,3-trans-substituted tetrahydrofurfuryl radicals 8 as the major intermediates.

β-Halogeno Ether Synthesis of Olefinic Alcohols: Stereochemistry and Conformation of 2-Substituted 3-Halogenotetrahydro-pyran and furan Precursors

Ring-scission of cis- or trans-2-alkyl- (or aryl-) 3-chlorotetrahydropyrans proceeds regioselectively and highly stereoselectively to give (E)-alk-4-en-1-ols, but in the parallel tetrahydrofuran series (Z)-/(E)-mixtures, dependent on percursor geometry, are formed.In this paper the stereochemistry and conformation of the tetrahydro-pyran and - furan precursors are considered.The cis/trans-composition of 2,3-dihalogenotetrahydro-pyrans and-furans made by various routes is reported.Reaction with Grignard reagents gives separable cis-/trans-mixtures the stereoisomeric composition of which, in the cases examined, does not depend on the stereoisomeric composition of the dihalide, but does vary with the halogen and the composition of the Grignard or dialkylmagnesium; possible reasons are discussed.The stereochemistry and conformation of the 2-alkyl- (or aryl-)3-chlorotetrahydropyrans is analysed by n.m.r. methods (J2a,3acis ca. 1.5 Hz; J2a,3atrans ca. 9.8 Hz) but assignments for the two tetrahydrofuran series with J2,3 2.6-3.6 and 4.3-5.9 are made uncertain by pseudorotation.The stereochemical identity of the two series is rigorously proved by isolation of cis- and trans-2-allyl-3-chlorotetrahydrofuran.On the one hand the former is hydrogenated to the cis-2-propyl compound, correlated with other members of the alkyl series, but on the other it is oxidised and the acid is converted into the cis-p-bromophenyl ester.The stereochemistry and conformation of the latter is rigorously demonstrated by an X-ray structure.The stereochemistries and conformations of the 2-deuterio- and 2-methoxy-3-chlorotetrahydropyrans are discussed, and consideration is then extended to the 2-alkyl-3-chloro-2-methyltetrahydro-pyran and -furan series.

Carbon-13 NMR Spectra of Saturated Heterocycles. XI - Tetrahydropyrans (Oxanes)

The 13C NMR spectra of 62 oxanes (tetrahydropyrans) with and without methyl substituents at various ring positions, some of them bearing in addition (or instead) ethyl, vinyl, ethynyl, carbomethoxy and methylol substituents at C-2, have been recorded, and the 294 resulting chemical shifts have been correlated by multiple linear regression analysis.Axial and equatorial α-, β-, γ-, δ-, gem- and vic-parameters for shifts caused by methyl groups at all ring positions, and similar parameters for Et, -CH=CH2, -CCH, CO2Me and CH2OH groups at C-2, are reported.Standard deviations of the parameters are, in most cases, within 0.3 ppm and the agreement of calculated and experimental shifts is excellent.This is probably the largest parameter set of this type extant. 13C NMR spectra of a number of additional substituted tetrahydropyrans, and of 3,6-dihydro-2H-pyrans and 3,4-dihydro-2H-pyrans, are tabulated and discussed.