128622-72-0

Upstream product

• 88116-46-5 1-butyl-2-cyclohexen-1-ol 
• 930-68-7 cyclohexenone 
• 108-05-4 vinyl acetate 
• 5323-87-5 3-Ethoxycyclohex-2-en-1-one 
• 504-02-9 1,3-cylohexanedione 
• 6301-49-1 3-butylcyclohexenone 

Downstream Products

• 141091-13-6 3-Allyl-1-butyl-cyclohexene 
• 1351381-79-7 4-(3-butyl-5-phenylfuran-2-yl)butanal 
• 1351381-80-0 4-(3-butyl-5-(4-methoxyphenyl)furan-2-yl)butanal 
• 141091-11-4 3-butylcyclohex-2-en-1-yl acetate 

Relevant academic research and scientific papers

Preparation of optically active cycloalkenes bearing all-carbon quaternary stereogenic centres: Via lipase-oxovanadium combo-catalysed dynamic kinetic resolution

In this study, a novel asymmetric synthesis of all-carbon quaternary stereogenic centres is developed by the connection of three prochiral or achiral components - conjugated enones, organometallic compounds and vinyl esters - at the C-1 position of the enones. This method involves three sequential steps: 1,2-nucleophilic addition of an organometallic compound to the enone, lipase-catalysed dynamic kinetic resolution (DKR) of the tert-allylic alcohol and the Ireland-Claisen rearrangement of the optically active allyl ester thus generated. This method features the effective use of acyl moieties installed by DKR for achieving high atom economy. The application of this method to the protective-group-free asymmetric total synthesis of (-)-crinane, a core structure of a class of natural alkaloids, has demonstrated that it can alter a known synthetic pathway of a racemate into an asymmetric synthesis of an optically pure molecule while reducing the total transformation steps and increasing the overall yield. With these advantages, this method is practical and attractive as a new environmentally benign protocol.

Catalytic stereospecific allyl-allyl cross-coupling of internal allyl electrophiles with allylB(pin)

Application of internal electrophiles in catalytic stereospecific allyl-allyl cross-coupling enable the rapid construction of multisubstituted 1,5-dienes, including those with all carbon quaternary centers. Compounds with minimal steric differentiation ca

Palladium-catalyzed oxidative rearrangement of tertiary allylic alcohols to enones with oxygen in aqueous solvent

A one-pot procedure for Pd(TFA)2-catalyzed 1,3-isomerization of tertiary allylic alcohols to secondary allylic alcohols followed by a Pd(TFA)2/neocuproine-catalyzed oxidative reaction to β-disubstituted-α,β-unsaturated kenones was developed. (Chemical Equation Presented).

1,n-rearrangement of allylic alcohols promoted by hot water: Application to the synthesis of navenone B, a polyene natural product

It was reported for the first time that hot water as a mildly acidic catalyst efficiently promoted 1,n-rearrangement (n = 3, 5, 7, 9) of allylic alcohols. In some cases, the rearrangement reactions joined isolated C-C double or triple bonds to generate conjugated polyene or enyne structure motifs. We used the 1,3-rearrangement reaction of an allylic alcohol in hot water as part of an attractive new strategy for construction of the polyene natural product navenone B by iterative use of a Grignard reaction, a 1,3-rearrangement of the resulting allylic alcohol, and subsequent oxidation of the rearranged product.

Domino reactions consisting of heterocyclization and 1,2-migration-redox- neutral and oxidative transition-metal catalysis

Two cats, two paths: Two novel domino reactions starting from 6-hydroxy-2-alkyl-2-alkynylcyclohexanones have been discovered. While redox-neutral platinum catalysis gives rise to furans through a sequence of cyclization, 1,2-shift, and Grob fragmentation, oxidative copper catalysis provides an entry to bicyclic 2,3-dihydrofurans. Upon cyclization and oxidation, an unusual benzilic acid rearrangement can take place in this case. Copyright

Mild and tunable benzoic acid catalysts for rearrangement reactions of allylic alcohols

An efficient and simple catalytic method for the isomerization of readily prepared allylic alcohols is described. We focus particularly on cyclic examples and the synthesis of unusual enyne and dienols. The benzoic acid catalysts employed are commercially available and very inexpensive and can be tuned for reactivity and substrate sensitivity.

Stereoselective aziridination of cyclic allylic alcohols using chloramine-T

The stereoselective aziridination of a range of cyclic allylic alcohols using two different chloramine salts (4-MeC6H4SO 2NClNa, TsNClNa and t-BuSO2NClNa, BusNClNa) has been explored. The stereoselectivity of these reactions was highly dependent on the structure of the allylic alcohol and the chloramine salt. Generally, mixtures of cis- and trans-hydroxy aziridines were obtained, in which the major diastereomer was the cis-hydroxy aziridine, whilst complete cis- diastereoselectivity was observed in the aziridination of 1,3-disubstituted allylic alcohols. In each case studied, aziridination using BusNClNa gave higher cis-stereoselectivity than that observed for the same reaction using TsNClNa. Unexpectedly, application of the aziridination conditions to 1-substituted cyclopen-2-en-1-ols did not generate the aziridines. Instead, epoxy sulfonamides were obtained.

Chemo-enzymatic preparation of optically active endo- bicyclo[4.1.0]heptan-2-ols

Resolutions of endo-bicyclo[4.1.O]heptan-2-ols were achieved by acylation in the presence of lipase from Candida antarctica (Novozym). The (1S,2R,6R) enantiomers reacted faster and the enantiomeric ratios were between 60 and 800 for the 6-substituted bicycloalkanols.

Synthesis of Carbocyclic Systems via Radical-Induced Epoxide Fragmentation

Cis-fused bicyclic compounds are synthesized from simple monocyclic enone precursors.The key step involves a tandem radical-mediated epoxide fragmentation, radical translocation, and cyclization.