17879-35-5

Usage

Uses

Used in Pharmaceutical Industry:
[(1S,3S)-3-acetyl-2,2-dimethylcyclobutyl]acetic acid is used as a potential component in the development of anti-inflammatory drugs due to its unique structural properties and the presence of the 2,2-dimethylcyclobutyl group. [(1S,3S)-3-acetyl-2,2-dimethylcyclobutyl]acetic acid's potential to alleviate inflammation and associated conditions is currently under investigation, with further research required to fully understand its uses and effects.
Used in Chemical Research:
In addition to its pharmaceutical applications, [(1S,3S)-3-acetyl-2,2-dimethylcyclobutyl]acetic acid is also utilized in chemical research for studying the properties and reactions of complex organic compounds with cyclobutyl rings and acetic acid functional groups. This research can contribute to the advancement of synthetic chemistry and the development of new compounds with various applications.

Upstream product

• 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 
• 80-56-8 Pinene 
• 22422-34-0 (1R,2R,3S,5R)-2,3-pinane diol 
• 28899-97-0 triphenylbismuth(V) diacetate 
• 18680-27-8 pinanediol 
• 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 
• 74281-23-5 1-((1R,3R)-3-(2,2-dimethoxyethyl)-2,2-dimethylcyclobutyl)ethan-1-one 

Downstream Products

• 4436-81-1 homoterpenylmethylketone 
• 21660-24-2 ((1S)-2.2-dimethyl-3t-acetohydroximoyl-cyclobutyl-(r))-acetic acid 
• 16978-11-3 methyl [(1SR,3SR)-3-acetyl-2,2-dimethylcyclobutyl]acetate 
• 4426-02-2 2,2-dimethyl-3-ethylcyclobutaneacetic acid 
• 2302-79-6 (+/-)-(3c-amino-2,2-dimethyl-cyclobut-r-yl)-acetic acid 
• 473-72-3 trans-(2,2-dimethyl-3-acetylcyclobutyl)acetic acid 
• 21660-24-2 (+/-)-[3c-(1-hydroxyimino-ethyl)-2,2-dimethyl-cyclobut-r-yl]-acetic acid 
• 938-94-3 (R,S)-2-(4'-methylphenyl) propionic acid 
• 28664-02-0 pinic acid 
• 144-62-7 oxalic acid 
• 79-91-4 terebic acid 
• 116-51-8 terpenylic acid 
• 61612-37-1 [3-(1-hydroxy-1-methyl-ethyl)-2,2-dimethyl-cyclobutyl]-acetic acid methyl ester 
• 24894-37-9 2-((1S,3S)-3-Acetyl-2,2-dimethyl-cyclobutyl)-N-benzyl-acetamide 

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.

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.

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.

Tetrapropylammonium perruthenate catalyzed glycol cleavage to carboxylic (Di)acids

A new method to accomplish glycol cleavage to carboxylic (di)acids in one step using catalytic amounts of tetrapropylammonium perruthenate (TPAP) together with N-methylmorpholine N-Oxide (NMO) as the stoichiometric oxidant is presented. In addition to regenerating the active catalyst, the N-oxide stabilizes intermediary carbonyl hydrates and thereby shifts a crucial equilibrium. The mild oxidation protocol is applicable to a broad range of substrates providing the respective acids, diacids, or keto acids in high yields.

2-Azapinanes: Aza Analogues of the Enantiomeric Pinyl Carbocation Intermediates in Pinene Biosynthesis

The enantiomeric 2-azapinanes, aza analogues of the pinyl carbocation intermediates in pinene biosynthesis, were synthesized from (-)-and (+)-cis-pinonic acids. The individual reactions in the 5-step sequence were Beckmann rearrangement of the pinonic acid oximes, cyclization to the N-acetyl lactams, hydrolysis to the NH-lactams, N-methylations, and LiAlH4 reductions. The anti stereochemistry of the N-methyl groups in the salts with respect to the gem-dimethyl bridge was established by NOE measurements and by X-ray diffraction analysis.(Figure Presented)