328010-06-6

Usage

Uses

Used in Pharmaceutical Industry:
(1R, 2R, 5S, 7R)-2,8,8,TRIMETHYL-3-AZATRICYCLO[5.1.1.0(2,5)]NONANE-4-ONE is used as a chiral building block for the synthesis of biologically active molecules. Its unique stereochemistry and functional groups make it a valuable starting material for the development of new drugs and pharmaceuticals.

Upstream product

• 1189-71-5 isocyanate de chlorosulfonyle 
• 7785-26-4 (-)-α-pinene 

Downstream Products

• 705948-99-8 C₁₁H₁₉NO₂ 
• 327611-82-5 (1R,2R,3S,5R)-2,6,6-Trimethyl-2-(3-phenyl-ureido)-bicyclo[3.1.1]heptane-3-carboxylic acid ethyl ester 
• 327611-80-3 1-((1R,2R,3S,5R)-3-Hydroxymethyl-2,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl)-3-phenyl-thiourea 
• 327611-76-7 (1R,2R,3S,5R)-2-amino-3-hydroxymethyl-2,6,6-trimethylbicyclo[3.1.1]heptane 

Relevant academic research and scientific papers

Synthesis, antimicrobial evaluation, and structure-activity relationship of α-pinene derivatives

Several (+)- and (-)-α-pinene derivatives were synthesized and evaluated for their antimicrobial activity toward Gram-positive bacteria Micrococcus luteus and Staphylococcus aureus, Gram-negative bacterium Escherichia coli, and the unicellular fungus Cand

Synthesis, antimicrobial evaluation, and structure-activity relationship of α-pinene derivatives

Several (+)- and (-)-α-pinene derivatives were synthesized and evaluated for their antimicrobial activity toward Gram-positive bacteria Micrococcus luteus and Staphylococcus aureus, Gram-negative bacterium Escherichia coli, and the unicellular fungus Candida albicans using bioautographic assays. (+)-α-Pinene 1a showed modest activity against the test organisms, whereas (-)-α-pinene 1b showed no activity at the tested concentration. Of all the α-pinene derivatives evaluated, the β-lactam derivatives (10a and 10b) were the most antimicrobial. The increase in the antimicrobial activity of 10a compared to 1a ranged from nearly 3.5-fold (C. albicans) to 43-fold (S. aureus). The mean ± standard deviation for the zone of inhibition (mm) for 10a (C. albicans) was 31.9 ± 4.3 and that for S. aureus was 51.1 ± 2.9. Although (-)-α-pinene 1b was not active toward the test microorganisms, the corresponding β-lactam 10b, amino ester 13b, and amino alcohol 14b showed antimicrobial activity toward the test microorganisms. The increase in the antimicrobial activity of 10b compared to 1b ranged from 32-fold (S. aureus) to 73-fold (M. luteus). The mean ± standard deviation for the zone of inhibition (mm) for 10b (S. aureus) was 32.0 ± 0.60 and that for M. luteus was 73.2 ± 0.30.

New chiral Schiff bases derived from (+)- and (-)-α-pinenes in the metal complex catalyzed asymmetric oxidation of sulfides

New chiral Schiff bases were derived from (+)- and (-)-α-pinenes for the first time. Coordinated to vanadium ions, they can be used as ligands in catalytic oxidation of sulfides into chiral sulfoxides. Conditions for the asymmetric oxidation of thioanisole to methyl phenyl sulfoxide in optical purity up to 32% were found. Variation of substituents in the ligand has a significant effect not only on enantioselectivity of the reaction, but also on absolute configuration of the sulfoxide formed.

Synthesis and transformations of enantiomeric 1,2-disubstituted monoterpene derivatives

Regio- and stereospecific addition of chlorosulfonyl isocyanate to (+)- and (-)-α-pinene 1 resulted in enantiomerically pure β-lactams 2, which were converted to enantiomeric β-amino esters 3 and 1,3-amino alcohols 4 and 6 with ee >99%. The resulting 1,3-