54385-25-0

Upstream product

• 79-10-7 acrylic acid 
• 78-79-5 isoprene 
• 56980-32-6 3-methyl-3-cyclohexene-1-carbonylaldehyde 
• 57-57-8 β-Propiolactone 
• 861575-47-5 3-bromo-3-methyl-cyclohexanecarboxylic acid 
• 814-68-6 acryloyl chloride 
• 1120-56-5 methylidenecyclobutane 
• 71-43-2 benzene 
• 110-86-1 pyridine 

Downstream Products

• 117015-88-0 (3R,4R)-4-Bromo-3-methoxy-3-methyl-cyclohexanecarboxylic acid methyl ester 
• 115664-07-8 3-Brom-4-methoxy-4-methyl-cyclohexan-1-carbonsaeuremethylester 
• 6493-78-3 3-methyl-3-cyclohexene-1-carboxylic acid methyl ester 
• 147118-85-2 3-methyl-3-phenylcyclohexanecarboxylic acid 
• 54446-42-3 3-Methyl-N-methyl-3-cyclohexencarboxamid 

Relevant academic research and scientific papers

Synthesis of the new (cyclopenta[b]pyrrolo[1,2-d])azepino[4,5-b]indole ring system

The 2-oxo functionalized title compound 1 was synthesised in 7 steps from tryptamine via rearrangement of the bromoiminium ion 13 in alkaline medium to azepinone 14 with concomitant formation of ketone 15. The ratio 14:15 was shown to depend on the nature of the hydroxide counter-ion.

Dehydro-aromatization of cyclohexene-carboxylic acids by sulfuric acid: Critical route for bio-based terephthalic acid synthesis

A novel dehydro-aromatization reaction under mild reaction conditions was successfully developed using sulfuric acid as a cost-effective and efficient oxidant. This reaction simplified the synthesis of terephthalic acid (TA, an important aromatic monomer precursor) from biomass-derived isoprene and acrylic acid.

Toward Diels-Alder reactions on a solid support using polymer bound N-substituted 3-hydroxy-4,4-dimethyl-2-pyrrolidinone acrylate derivatives

Several N-substituted 3-hydroxy-4,4-dimethyl-2-pyrrolidinone acrylate derivatives, selected to allow their attachment to a polymer, have been prepared and tested as dienophiles in the Diels-Alder reaction. The experiments, performed under TiCl4 catalysis in solution or the solid phase with isoprene and cyclopentadiene as dienes, pointed out the difficulties associated with some of these compounds that failed to give the corresponding cycloadduct. 13C NMR studies provided some evidence regarding the nature of the interactions between the acrylate compounds and TiCl4. It appears that the outcome of the reaction is dependent on the acrylate structure and that the 4-(3-hydroxy-4,4-dimethyl-2-oxopyrrolidin-1-yl)benzoic acid acrylate derivatives are highly efficient to give the cycloadduct in good yield and with high regio- or endoselectivity in both solution and solid-phase reaction conditions. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

(R)- or (S)-4-(3-hydroxy-4,4-dimethyl-2-oxopyrrolidin-1-yl)benzoic acid as a new chiral auxiliary for solid phase asymmetric Diels-Alder reactions

The synthesis of enantiopure (R)- and (S)-4-(3-hydroxy-4,4-dimethyl-2- oxopyrrolidin-1-yl)benzoic acid is described and the corresponding supported chiral acrylate derivative has been used as a dienophile in solid phase asymmetric Diels-Alder reactions wi

Diels-Alder reactions in pyridinium based ionic liquids

Diels-Alder reactions have been investigated in pyridinium based ionic liquids. These solvents are found to be more effective compared to the organic solvent studied, in enhancing the reaction rate and product yields. Recycled ionic liquids also gave exce

Fructose-derived ionic liquids: Recyclable homogeneous supports

A new homogeneous support has been developed that is based on a fructose-derived ionic liquid. It has been applied to the preparation of a series of supported Diels-Alder adducts. The cleavage of these adducts from the ionic liquid has resulted in some interesting observations regarding the base stability of imidazolium cations. Using a transesterification cleavage, the ionic support can be recovered and recycled.

ORGANOMANGANESE (II) REAGENTS XIV: A SHORT AND EFFICIENT SYNTHESIS OF DIASTEREOISOMERIC (+/-)-α-BISABOLOLS AND (+/-)-CHLORPHENOXAMINE

Diastereomeric (+/-)-α-bisabolols (7), a sesquiterpenoid alcohol, and (+/-)-chlorphenoxamine (12), an antihistamine, have been prepared in excellent yields.Both these short and convenient syntheses involve as a key step the one-pot elaboration of a dissymetrical tertiary alcohol via an organomanganese reagent (5 to 7 and 9 to 10 respectively).

Acyloxyborane: An Activating Device for Carboxylic Acids

We chose α,β-unsaturated acids and investigated the reactivity of their borane adducts in Diels-Alder reactions.The reaction did proceed smoothly and has been found to be a useful method for synthesis of carboxylic acids.