29293-06-9

Usage

InChI:InChI=1/C6H12O2/c1-6(2-4-7)3-5-8/h2,7-8H,3-5H2,1H3/b6-2+

Upstream product

• 10021-22-4 3,6-dihydro-4-methyl-2H-pyran-2-one 
• 67116-19-2 3-methyl-pentenedioic acid anhydride 
• 52313-87-8 3-methyl-2-pentene-1,5-diacid dimethyl 
• 50-00-0 formaldehyd 
• 115-11-7 isobutene 
• 2381-87-5 4-methyl-5,6-dihydro-2H-pyran-2-one 
• 6158-90-3 5-hydroxy-3-methyl-pent-3t-enoic acid 
• 763-32-6 2-methyl-1-buten-4-ol 
• 674-26-0 mevalonolactone 
• 53120-74-4 3,3-dimethylpent-1,5-diol 
• 372-42-9 3-methylpent-2-enedioic acid 
• 53358-18-2 (Z)-2-methyl-pentenedioic acid diethyl ester 

Downstream Products

• 133545-68-3 3,3-dimethyl-2(cis-3-methyl-5-bromo-2-ene)pentyl cyclohexanone 

Relevant academic research and scientific papers

Facile synthesis of anhydromevalonolactone from ethyl acetoacetate

Ethyl acetoacetate was transformed to 3-methylglutaconic anhydride, which upon LAH reduction and Jones oxidation afforded anhydromevalonolactone.

POLYMERS PREPARED FROM MEVALONOLACTONE AND DERIVATIVES

Described herein polymer precursor compounds (aka polymer building blocks) of derived from biobased compounds, and specifically biobased mevalonolactone and its related derivatives. Through oxidation these biobased precursors can be reacted to yield building blocks for (unsaturated-) polyesters, polyester polyols and polyamides, as well as precursors for glycidyl esters and omega-alkenyl esters. Through reduction, these biobased precursors can be reacted to yield building blocks for (unsaturated-) polyesters, polyester polyols, polycarbonates, as well as precursors for glycidyl ethers and omega-alkenyl ethers. Through nucleophilic ring opening and/or amidation, these biobased precursors can be reacted to yield building blocks for polyester polyols, chain-extender for polyurethanes, or polyester-amides.

POLYMERS PREPARED FROM MEVALONOLACTONE AND DERIVATIVES

Described herein polymer precursor compounds (aka polymer building blocks) of derived from biobased compounds, and specifically biobased mevalonolactone and its related derivatives. Through oxidation these biobased precursors can be reacted to yield building blocks for (unsaturated-) polyesters, polyester polyols and polyamides, as well as precursors for glycidyl esters and omega-alkenyl esters. Through reduction, these biobased precursors can be reacted to yield building blocks for (unsaturated-) polyesters, polyester polyols, polycarbonates, as well as precursors for glycidyl ethers and omega-alkenyl ethers. Through nucleophilic ring opening and/or amidation, these biobased precursors can be reacted to yield building blocks for polyester polyols, chain-extender for polyurethanes, or polyester-amides.

Quaternary Stereogenic Centers through Enantioselective Heck Arylation of Acyclic Olefins with Aryldiazonium Salts: Application in a Concise Synthesis of (R)-Verapamil

We describe herein a highly regio- and enantioselective Pd-catalyzed Heck arylation of unactivated trisubstituted acyclic olefins to provide all-carbon quaternary stereogenic centers. Chiral N,N ligands of the pyrimidine- and pyrazino-oxazoline class were developed for that purpose, providing the desired products in good to high yields with enantiomeric ratios up to >99:1. Both linear and branched substituents on the olefins were well-tolerated. The potential of this new method is demonstrated by the straightforward synthesis of several O-methyl lactols and lactones containing quaternary stereocenters, together with a concise enantioselective total synthesis of the calcium channel blocker verapamil.

SYNTHESIS OF (+/-)-α-CHAMIGRENE

Regiospecific spiroalkylation of the selectively generated enolate arising from the 1,4-addition of lithium dimethylcuprate to 3-methylcyclohex-2-en-1-one allows an efficient preparation of spiroketones, including a key intermediate for the synthesis of (+/-)-α-Chamigrene.

DIMETHYLALUMINUM CHLORIDE CATALYZED ENE REACTIONS OF ALDEHYDES.

Dimethylaluminum chloride, which is a mild Lewis acid and a proton scavenger, catalyzes the ene reactions of aliphatic and aromatic aldehydes with alkenes containing a disubstituted vinylic carbon. Proton-initiated rearrangements do not occur, since the alcohol-Lewis acid complex formed in the ene reaction reacts rapidly to give methane and a nonacidic aluminum alkoxide. Formaldehyde and excess Me//2AlCl give good yields of ene adducts with all types of alkenes. With 1 equiv of Me//2AlCl, formaldehyde and mono- and 1,2-disubstituted alkenes give gamma -chloro alcohols resulting from cis addition of chlorine and hydroxymethyl groups to the double bond. This work is pertinent to the synthesis of alcohols.

Reaction of Dinitrogen Tetraoxide with Hydrophilic Olefins: Synthesis of Citric and 2-Hydroxy-2-methylbutanedioic Acids

Liquid olefins typically react with N2O4 by free-radical reactions to form dinitro and nitronitrite derivatives.Introduction of hydrophilic substituents into 1-olefins altered the course of the reaction of the olefins with N2O4 in aqueous HNO3.Citric acid was formed in 64 mol percent yield by the reaction of 3-methylene-1,5-pentanediol with N2O4 in aqueous HNO3.Similarly, 2-hydroxy-2-methylbutanedioic acid was made from 3-methyl-3-buten-1-ol in 88percent yield.These results are explained by solution of the hydrophilic olefins in aqueous HNO3-N2O4 and addition of N2O4 to the double bond as NO+ and NO3- ions to yield nitrosonitrates, which react further to give the final products.