327611-65-4

Basic information

• Product Name: (1S,2S,3R,5S)-(2-AMINO-2,6,6-TRIMETHYL-BICYCLO[3.1.1]HEPT-3-YL)-METHANOL
• Synonyms: (1S,2S,3R,5S)-(2-AMINO-2,6,6-TRIMETHYL-BICYCLO[3.1.1]HEPT-3-YL)-METHANOL
• CAS NO: 327611-65-4
• Molecular Formula: C₁₁H₂₁NO
• Molecular Weight: 183.29
• Mol File: 327611-65-4.mol

Chemical Properties

• Boiling Point: 257.5°C at 760 mmHg
• Flash Point: 109.6°C
• Appearance: /
• Density: 0.973g/cm³
• Vapor Pressure: 0.00215mmHg at 25°C
• Refractive Index: 1.486
• CAS DataBase Reference: (1S,2S,3R,5S)-(2-AMINO-2,6,6-TRIMETHYL-BICYCLO[3.1.1]HEPT-3-YL)-METHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (1S,2S,3R,5S)-(2-AMINO-2,6,6-TRIMETHYL-BICYCLO[3.1.1]HEPT-3-YL)-METHANOL(327611-65-4)
• EPA Substance Registry System: (1S,2S,3R,5S)-(2-AMINO-2,6,6-TRIMETHYL-BICYCLO[3.1.1]HEPT-3-YL)-METHANOL(327611-65-4)

Safety Data

• Hazardous Substances Data: 327611-65-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(1S,2S,3R,5S)-(2-AMINO-2,6,6-TRIMETHYL-BICYCLO[3.1.1]HEPT-3-YL)-METHANOL could be used as a building block or intermediate in the synthesis of pharmaceutical compounds due to its unique structure and functional groups, which may allow for the development of new drugs with specific therapeutic properties.
Used in Chemical Synthesis:
In the field of organic chemistry, (1S,2S,3R,5S)-(2-AMINO-2,6,6-TRIMETHYL-BICYCLO[3.1.1]HEPT-3-YL)-METHANOL might be used as a reactant or catalyst in various chemical reactions, taking advantage of its reactivity and stereochemistry to produce desired products with high selectivity.
Used in Material Science:
The unique structural features of (1S,2S,3R,5S)-(2-AMINO-2,6,6-TRIMETHYL-BICYCLO[3.1.1]HEPT-3-YL)-METHANOL could make it a candidate for the development of new materials with specific properties, such as polymers with tailored characteristics or advanced materials for various applications.

InChI:InChI=1/C11H21NO/c1-10(2)7-4-8(6-13)11(3,12)9(10)5-7/h7-9,13H,4-6,12H2,1-3H3/t7-,8+,9+,11-/m1/s1

Upstream product

• 327611-64-3 ethyl (1S,2S,3R,5S)-2-amino-2,6,6-trimethylbicyclo[3.1.1]heptane-3-carboxylate 
• 35182-62-8 (1S,2S,5R,7S)-2,8,8-trimethyl-3-azatricyclo[5.1.1.0^2,5]nonan-4-one 
• 7785-70-8 (+)-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

• 327611-69-8 1-((1S,2S,3R,5S)-3-Hydroxymethyl-2,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl)-3-phenyl-thiourea 
• 1174375-56-4 6-[(1S,2S,7R,9S)-2,10,10-trimethyl-5-oxa-3-azatricyclo[7.1.1.0(2,7)]undec-4-yl]-2,4-dinitrophenol 
• 1092822-22-4 2-{[(1S,2S,3R,5S)-3-hydroxymethyl-2,6,6-trimethylbicyclo[3.1.1]hept-2-ylimino]methyl}phenol 
• 1254176-18-5 2-tert-butyl-6-({(1S,2S,3R,5S)-3-hydroxymethyl-2,6,6-trimethylbicyclo[3.1.1]hept-2-ylimino}methyl)-4-(2-methoxyethyl)phenol 
• 1312714-84-3 2-((E)-((1S,2S,3R,5S)-3-(hydroxymethyl)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ylimino)methyl)-6-methylphenol 
• 1174375-54-2 2,4-di-tert-butyl-6-((E)-((1S,2S,3R,5S)-3-(hydroxymethyl)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ylimino)methyl)phenol 
• 1312714-85-4 2-tert-butyl-6-((E)-((1S,2S,3R,5S)-3-(hydroxymethyl)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ylimino)methyl)-4-methylphenol 
• 1174375-63-3 5-(diethylamino)-2-((E)-((1S,2S,3R,5S)-3-(hydroxymethyl)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ylimino)methyl)phenol 
• 1174375-57-5 2-((E)-((1S,2S,3R,5S)-3-(hydroxymethyl)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ylimino)methyl)phenol 
• 1312714-86-5 4-bromo-2-((E)-((1S,2S,3R,5S)-3-(hydroxymethyl)-2,6,6-trimethylbicyclo[3.1.1]heptan-2-ylimino)methyl)phenol 

Relevant articles and documents

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.

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.

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-