14211-72-4

Upstream product

• 52908-82-4 5-methyl-5-pentyldihydro-2(3H)-furanone 
• 51575-16-7 decane-2,5-dione 
• 100054-95-3 3-butyl-2-methyl-4-oxo-cyclopent-2-enecarboxylic acid amide 
• 100532-91-0 3-butyl-2-methyl-4-oxo-cyclopent-2-enecarboxylic acid ethyl ester 
• 69065-35-6 dec-3t-en-5-one 
• 854854-35-6 2-acetonyl-3-oxo-octanoic acid methyl ester 
• 64-19-7 acetic acid 
• 142-62-1 hexanoic acid 
• 20577-46-2 4,7-dioxooctanoic acid 
• 133849-26-0 N-hexanoyl-DL-valine 
• 488-09-5 2-(2-butenyl)-3-methyl-2-cyclopentenone 
• 142-61-0 Hexanoyl chloride 
• 539-88-8 4-oxopentanoic acid ethyl ester 
• 693-25-4 n-pentylmagnesium bromide 

Downstream Products

• 123-76-2 levulinic acid 
• 101428-55-1 2-butyl-3-methyl-cyclopent-2-enone-(2,4-dinitro-phenylhydrazone) 

Relevant academic research and scientific papers

Mechanism of Ru(II)-Catalyzed Rearrangements of Allenyl- and Alkynylcyclopropanols to Cyclopentenones

A comparison study of the Ru(II)-catalyzed rearrangements of allenyl- and alkynylcyclopropanols to the corresponding cyclopentenones has been undertaken with the aid of an alkyl substituent on the three-membered ring. These ring expansion reactions proceed with exceptional regioselectivity irrespective of the cis/trans stereochemistry of the substituents on the three-membered ring. β-Carbon elimination is the common feature in the absence of a chelating group at the 4′-position in the alkyne chain.

Synthesis of Pyrethroids and Jasmonoids through Palladium-Catalyzed Cross-Coupling Reactions

The synthesis of jasmone and related jasmonoids and pyrethroids is described. These compounds play a defensive role in plants and share a common cyclopentenone core with variations in the side chains. Jasmone, cinerone, allylrethrone, and derivatives were synthesized through -allyl palladium cross-coupling of stannane derivatives. With selective hydrogenation, dihydrojasmone, and dihydrocinerone were also synthesized.

A novel tandem [2 + 2] cycloaddition-Dieckmann condensation with ynolate anions. Efficient synthesis of substituted cycloalkenones and naphthalenes via formal [n + 1] cycloaddition

A novel tandem [2 + 2] cycloaddition-Dieckmann condensation via ynolate anions is described. Ynolate anions are useful for the formation of reactive β-lactone enolates via a pathway not involving the enolization of the corresponding β-lactones. The [2 + 2] cycloaddition of ynolate anions with δ- or σ-keto esters, followed by Dieckmann condensation, gives bicyclic β-lactones, which are easily decarboxylated to produce synthetically useful 2,3-disubstituted cyclopentenones and cyclohexenones in one pot. This tandem reaction was applied to a novel, one-pot synthesis of highly substituted naphthalenes.

Strictly regiocontrolled α-monosubstitution of cyclic carbonyl compounds with alkynyl and alkyl groups via Pd-catalyzed coupling of cyclic α-iodoenones with organozincs

The conditions for the Pd-catalyzed cross coupling of cyclic α-iodoenones, such as 2-iodo-2-cyclohexenone, with alkynylzincs have been optimized. The use of tris(o-furyl)phosphine (TFP) as a ligand and DMF as a solvent has led to the formation of α-alkynylenones in excellent yields. This optimized procedure has been applied to the synthesis of (±)-harveynone and (±)-tricholomenyn A in high yields. Investigation of related α-alkylation reactions using alkylzincs has revealed the following. Methylzinc and primary alkylzinc derivatives readily undergo Pd-catalyzed cross coupling with α-iodoenones. Although (s-Bu)2Zn also undergoes Pd-catalyzed cross coupling, only the n-Bu-substituted products were obtained, α-Benzylation and α-homobenzylation can proceed satisfactorily, whereas allylzinc and propargylzinc derivatives undergo only addition to the carbonyl group. Although some promising results have been obtained in α-homoallylation and α-homopropargylation, these reactions need to be further improved. (C) 2000 Elsevier Science Ltd.

Synthesis of bis(1,2,3-substituted cyclopentadienyl)zirconium dichloride derivatives and their use in ethylene polymerization

Catalytic Pauson-Khand reaction products with norbornadiene could be effectively transformed to trisubstituted cyclopentadienes, which have been used to synthesize a series of unbridged bis(1-R′-2-R-3-R′-trisubstituted cyclopentadienyl)zirconium dichlorid

Reaction of cyclic α-hydroxy epoxides with a strong base: A new 1,2-rearrangement, evidence for a carbenoid pathway

Several substituted five- and six-membered cyclic α,β-unsaturated ketones are readily available by treatment of the corresponding α-hydroxy epoxides with an organolithium reagent. The reaction involves a new carbenoid 1,2-alkyl rearrangement. Evidence for the carbenoid intermediate has been obtained by an intramolecular trapping of the highly reactive species.

A NEW SYNTHESIS OF DIHYDROJASMON

Strictly controlled hydrolysis of 5-methylene-4,5-dihydrofurans 3 allows an efficient approach to 2-acetonyl-1,3-dicarbonyl compounds 4, key intermediates in the synthesis of cyclopentenone derivatives.

A SIMPLE SYNTHESIS OF DIHYDROJASMONE

Acetalization of a γ-substituted α,β-unsaturated ketone, followed by acid hydrolysis gave a cyclopentenone.

A Convenient Preparative Method of Jasmone and its Related Compounds

The reaction of (Z)-hept-4-enoic acid (1) with vinylmagnesium bromide gave (Z)-undeca-1,8-dien-5-one (2).The oxidation of the terminal vinylic group of (2) affords (Z)-undec-8-ene-2,5-dione (3).Jasmone (4) was obtained by the usual alkali cyclization of (3).A variety of alkylcyclopentenones were prepared by the same method.