328010-05-5

Usage

Uses

Used in Medicinal Chemistry:
(1S, 2S, 5R, 7S)-2,8,8,TRIMETHYL-3-AZATRICYCLO[5.1.1.0(2,5)]NONANE-4-ONE is used as a complex organic molecule for the development of new drugs and pharmaceutical agents. Its unique structure and chiral centers may offer novel interactions with biological targets, leading to the discovery of new therapeutic agents.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, (1S, 2S, 5R, 7S)-2,8,8,TRIMETHYL-3-AZATRICYCLO[5.1.1.0(2,5)]NONANE-4-ONE is used as a key intermediate in the synthesis of various drug candidates. Its complex structure and chirality can be leveraged to create innovative medicines with improved efficacy and selectivity.
Used in Chemical Research:
(1S, 2S, 5R, 7S)-2,8,8,TRIMETHYL-3-AZATRICYCLO[5.1.1.0(2,5)]NONANE-4-ONE is used as a research compound in chemical studies, where its unique properties and structure can be explored for understanding molecular interactions, chirality, and the development of new synthetic methods.

Upstream product

• 1189-71-5 isocyanate de chlorosulfonyle 
• 7785-70-8 (+)-α-pinene 
• 62697-75-0 (-)-isopinocamphyl tosylate 
• 7785-26-4 (-)-α-pinene 
• 37500-21-3 (1S,2S,5R,7S)-2,8,8-Trimethyl-4-oxo-3-aza-tricyclo[5.1.1.0^2,5]nonane-3-sulfonyl chloride 

Downstream Products

• 705949-09-3 C₁₂H₂₁NO₂ 
• 1474047-41-0 tert-butyl (1S,2S,3R,5S)-2,6,6-trimethyl-3-{[(R)-1-phenylethyl]carbamoyl}bicyclo[3.1.1]heptan-2-ylcarbamate 
• 1474047-44-3 methyl (S)-2-{(1S,2S,3R,5S)-2-[(tert-butoxycarbonyl)amino]-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ylcarboxamido}-3-phenylpropanoate 
• 1474047-58-9 benzyl (S)-2-({(1S,2S,3R,5S)-2-[(tert-butoxycarbonyl)amino]-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ylcarboxamido}methyl)pyrrolidine-1-carboxylate 
• 1474047-45-4 (1S,2S,3R,5S)-2-amino-2,6,6-trimethyl-N-[(R)-1-phenylethyl]bicyclo[3.1.1]heptane-3-carboxamide 
• 1474047-48-7 methyl (S)-2-{(1S,2S,3R,5S)-2-amino-2,6,6-trimethylbicyclo[3.1.1]heptan-3-ylcarboxamido}-3-phenylpropanoate 
• 1474047-49-8 benzyl (S)-2-({(1S,2S,3R,5S)-2,6,6-trimethyl-3-{[(R)-1-phenylethyl]carbamoyl}bicyclo[3.1.1]heptan-2-yl}carbamoyl)pyrrolidine-1-carboxylate 
• 1474047-51-2 benzyl (S)-2-({(1S,2S,3R,5S)-3-{[(R)-3,3-dimethylbutan-2-yl]carbamoyl}-2,6,6-trimethylbicyclo[3.1.1]heptan-2-yl}carbamoyl)pyrrolidine-1-carboxylate 
• 1474047-52-3 benzyl (S)-2-({(1S,2S,3R,5S)-3-{[(S)-1-methoxy-1-oxo-3-phenylpropan-2-yl]carbamoyl}-2,6,6-trimethylbicyclo[3.1.1]heptan-2-yl}carbamoyl)pyrrolidine-1-carboxylate 
• 1474047-53-4 benzyl (S)-2-{[(1S,2S,3R,5S)-3-(methoxycarbonyl)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-yl]carbamoyl}pyrrolidine-1-carboxylate 
• 1474047-54-5 (1S,2S,3R,5S)-2-{(S)-1-[(benzyloxy)carbonyl]pyrrolidin-2-ylcarboxamido}-2,6,6-trimethylbicyclo[3.1.1]heptane-3-carboxylic acid 
• 1474047-59-0 (S)-N-{(1S,2S,3R,5S)-2,6,6-trimethyl-3-{[(R)-1-phenylethyl]carbamoyl}bicyclo[3.1.1]heptan-2-yl}pyrrolidine-2-carboxamide 
• 1474047-62-5 methyl (S)-3-phenyl-2-{(1S,2S,3R,5S)-2,6,6-trimethyl-2-[(S)-pyrrolidin-2-ylcarboxamido]bicyclo[3.1.1]heptan-3-ylcarboxamido}propanoate 
• 1474047-56-7 (S)-3-phenyl-2-{(1S,2S,3R,5S)-2,6,6-trimethyl-2-[(S)-pyrrolidin-2-ylcarboxamido]bicyclo[3.1.1]heptan-3-ylcarboxamido}propanoic acid 

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.

Stereoselective synthesis of chiral pyrrolidine derivatives of (+)-α-pinene containing a β-amino acid moiety

We report the synthesis of several enantiopure pyrrolidine derivatives containing a β-amino acid moiety. These novel chiral compounds were prepared through stereospecific chlorosulfonyl isocyanate (CSI) addition to the readily available, natural terpene (+)-α-pinene. Coupling of N-Boc-protected β-amino acid derivatives with various bulky amines and amino acids using the mixed anhydride activation method, followed by N-deprotection, afforded the corresponding chiral amino amides in good yields. Despite the severe steric hindrance anticipated in α-pinene-based heterocycles, efficient coupling of the amino amides and an amino ester with the acyl chloride of N-Cbz-protected (S)-proline provided the corresponding pyrrolidinic pinene derivatives in good yields. Moreover, a convenient synthesis of N-Cbz- and N-Boc-monoprotected (S)-prolinamine is reported. Georg Thieme Verlag Stuttgart New York.

α-Pinene-type chiral Schiff bases as tridentate ligands in asymmetric addition reactions

A group of tridentate Schiff bases derived from (+)-α-pinene were synthesized. The steric effects in the transition state, the importance of π-π stacking interactions as well as the electronic effects of aryl aldehydes according to Hammett constant values in the enantioselective addition of Et2Zn to aldehydes with the use of Schiff bases as chiral ligands are described. Also, a variety of aldehydes were cyanated using a catalyst prepared in situ from titanium tetraisopropoxide and chiral Schiff bases. The influence of a conjugated double-bond in the cyanation substrates on enantioselectivity was observed. The chemical structures of the chiral Schiff base-titanium alkoxide complexes are discussed based on their 1H and 13C NMR spectra. 3D models of the Zn2-complex catalyst and Ti-complex catalyst containing α-pinane-type Schiff bases based on X-ray diffraction experiments are postulated. The models presented were consistent with the reported chirality of the addition product and observed ee.

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.

Regio- and stereoselective synthesis of the enantiomers of monoterpene-based β-amino acid derivatives

The regio- and stereospecific addition of chlorosulfonyl isocyanate to cis-δ-pinene enantiomers has furnished monoterpene-fused β-lactams. The observed regioselectivity can be explained by ab initio DFT modeling of transition state structures. In contrast with the less reactive α-pinane-fused β-lactam 4, the resulting β-lactams 5 and 13 containing an amino group connected to a secondary carbon possess similar reactivity to the cycloalkane-fused analogues and can be easily converted to the β-amino acid and its protected derivatives. The base-catalyzed isomerization of the cis-amino ester afforded the corresponding trans-amino ester in moderate yield.

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-