64396-97-0

Usage

Structure

Cyclobutyl ring with an acetyl group and a carboxylic acid group attached

Derivative

Cyclobutylacetic acid

Potential use

Intermediate for the synthesis of pharmaceuticals and other organic compounds

Value

Unique structure and properties for medicinal and research purposes

Need for further research

To fully understand potential applications and effects.

Upstream product

• 80-56-8 Pinene 
• 18680-27-8 pinanediol 
• 21803-49-6 (1S,2S,3R,5S)-(+)-pinanediol 
• 7785-26-4 (-)-α-pinene 
• 18358-53-7 pinocamphone 
• 74281-22-4 2-((1R,3R)-3-acetyl-2,2-dimethylcyclobutyl)acetaldehyde 
• 7785-70-8 (+)-α-pinene 
• 22422-34-0 (1R,2R,3S,5R)-2,3-pinane diol 
• 28899-97-0 triphenylbismuth(V) diacetate 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 1845-25-6 (1S,2S,5S)-(-)-2-hydroxypinan-3-one 
• 67-63-0 isopropyl alcohol 
• 54-85-3 isoniazid 
• 936-02-7 2-Hydroxybenzoylhydrazine 

Downstream Products

• 473-72-3 (-)-trans-pinonoic acid 
• 21660-24-2 ((1S)-2.2-dimethyl-3c-acetohydroximoyl-cyclobutyl-(r))-acetic acid 
• 80408-87-3 (+)-5,5-dimethyl-4-(3-oxobutyl)tetrahydrofuran-2-one 
• 4436-81-1 homoterpenylmethylketone 
• 126892-32-8 1-((1S,3R)-3-Hydroxymethyl-2,2-dimethyl-cyclobutyl)-ethanone 
• 126892-29-3 1-((1S,3R)-2,2-Dimethyl-3-phenylselanylmethyl-cyclobutyl)-ethanone 
• 4951-98-8 ((1S)-2.2-dimethyl-3c-ethoxycarbonyl-cyclobutyl-(r))-acetic acid ethyl ester 

Relevant academic research and scientific papers

Molecular Chirality and Cloud Activation Potentials of Dimeric α-Pinene Oxidation Products

The surface activity of ten atmospherically relevant α-pinene-derived dimers having varying terminal functional groups and backbone stereochemistry is reported. We find ～10% differences in surface activity between diastereomers of the same dimer, demonstrating that surface activity depends upon backbone stereochemistry. Octanol-water (KOW) and octanol-ammonium sulfate partitioning coefficient (KOAS) measurements of our standards align well with the surface activity measurements, with the more surface-active dimers exhibiting increased hydrophobicity. Our findings establish a link between molecular chirality and cloud activation potential of secondary organic aerosol particles. Given the diurnal variations in enantiomeric excess of biogenic emissions, possible contributions of such a link to biosphere:atmosphere feedbacks as well as aerosol particle viscosity and phase separation are discussed.

Transformations of Peroxide Ozonolysis Products of (–)-α-Pinene and (+)-3-Carene by the Action of 4-Hydroxybenzohydrazide

Abstract: Treatment of peroxide ozonolysis products of the bicyclic monoterpenes (–)-α-pinene and (+)-3-carene with 4-hydroxybenzohydrazide in methylene chloride or tetrahydrofuran gave the corresponding keto acids, whereas keto esters were formed in methanol.

Synthesis of Isonicotinic and Salicylic Acids Derivatives from (–)-α-Pinene and (+)-Δ3-Carene

Abstract: Optically active cyclobutanediyl- and cyclopropanediylbisalkylidenedihydrazides of isonicotinic and salicylic acids were synthesized when theperoxide products of ozonolysis of (–)-α-pinene and(+)-Δ3-carene were reduced with isonicotin

Synthesis of optically active macrolides bearing di- and triethylene glycol and dicarboxylic acid hydrazide moieties from (-)-α-pinene

Six optically active macroheterocycles bearing ester and dihydrazide moieties were synthesized from available natural (-)-α-pinene through the intermediate keto acid, (31R,33R)- 1-hydroxy-32,32-dimethyl-1,4-dioxopentaphane, using the [2+1] reaction of this keto acid with di- or triethylene glycols and the [1+1] condensation of the resulting α,ω-diketo diesters with dicarboxylic acid dihydrazides in the key steps.

Sodium Hypochlorite Pentahydrate as a Reagent for the Cleavage of trans-Cyclic Glycols

Sodium hypochlorite pentahydrate (NaOCl·5H2O) can be used toward the efficient glycol cleavage of trans-cyclic glycols, which are generally resistant to this transformation. Interestingly, the reaction of cis-cyclic glycols with NaOCl·5H2O is slower than that observed for the corresponding trans-isomer. This trans selectivity is in sharp contrast to traditional oxidants used for glycol cleavage. Acyclic glycols can also react efficiently with NaOCl·5H2O to form their corresponding carbonyl compounds in high yield.

Transformations of (-)-α-pinene peroxide ozonolysis products by hydrazines of HCL and H2SO4

The reactivities of hydrazines of HCl and H2SO4 for (-)-α-pinene peroxide ozonolysis products were studied. It was shown that these reagents were less effective and selective than semicarbazide hydrochloride for transformations into cis-pinonic acid and its esters.

Transformations of peroxide products of olefin ozonolysis in tetrahydrofuran in reactions with hydroxylamine and semicarbazide hydrochlorides

Treatment with hydroxylamine and semicarbazide hydrochlorides of peroxide products obtained by ozonolysis of olefins in tetrahydrofuran gives mainly carboxylic acids and their derivatives.

Transformation of peroxide products of olefin ozonolysis under treatment with hydroxylamine and semicarbazide hydrochlorides in acetic acid

Hydrochlorides of hydroxylamine and semicarbazide efficiently reduce peroxide products of olefin ozonolysis in a system CH2Cl2-AcOH leading to the formation of carboxylic acids and their derivatives. The application of water as the solvent component favors the increase in the fraction of nitrogen-containing organic compounds (semicarbazones, keto- and aldoximes, nitriles) and reduction in the yield of carboxylic acids.

Oxidation of terpenoid diols with chlorine dioxide: Preparation of ketols and α-chlorohydroxyketones of carane and pinane structures

Vicinal terpenoid diols of carane- and pinane-type structures have been oxidized with chlorine dioxide in pyridine to form the corresponding ketols in the preparative yield of 52-72%, the selectivity of α-hydroxyketones formation being 80-90%. It has been shown that the diols reactivity towards oxidation with ClO2 depends mainly on the stereochemistry of hydroxy groups. The catalysts, VO(acac)2, Mo(CO6), and MoCl 5 have practically no effect on the oxidation process. When the reaction has been performed in dimethylformamide, the hydroxyketone chlorination occurred at high conversion.

Efficient synthesis of chiral Δ2-1,3,4-thiadiazolines from α-pinene and verbenone

The synthesis of chiral cyclobutane 1,3,4-thiadiazoline derivatives starting from (-)-α-pinene and (-)-verbenone was studied. The diastereoisomeric excesses of the products obtained depended strongly upon the starting chiral ketone. The stereochemical assignments of the synthesized compounds were performed by NMR spectroscopy, X-ray analysis, and theoretical calculations.