327611-76-7

Basic information

• Product Name: (1R,2R,3S,5R)-(2-AMINO-2,6,6-TRIMETHYL-BICYCLO[3.1.1]HEPT-3-YL)-METHANOL
• Synonyms: (1R,2R,3S,5R)-(2-AMINO-2,6,6-TRIMETHYL-BICYCLO[3.1.1]HEPT-3-YL)-METHANOL
• CAS NO: 327611-76-7
• Molecular Formula: C₁₁H₂₁NO
• Molecular Weight: 183.29
• Mol File: 327611-76-7.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: (1R,2R,3S,5R)-(2-AMINO-2,6,6-TRIMETHYL-BICYCLO[3.1.1]HEPT-3-YL)-METHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R,3S,5R)-(2-AMINO-2,6,6-TRIMETHYL-BICYCLO[3.1.1]HEPT-3-YL)-METHANOL(327611-76-7)
• EPA Substance Registry System: (1R,2R,3S,5R)-(2-AMINO-2,6,6-TRIMETHYL-BICYCLO[3.1.1]HEPT-3-YL)-METHANOL(327611-76-7)

Safety Data

• Hazardous Substances Data: 327611-76-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(1R,2R,3S,5R)-(2-AMINO-2,6,6-TRIMETHYL-BICYCLO[3.1.1]HEPT-3-YL)-METHANOL is used as a building block for the synthesis of pharmaceuticals, contributing to the development of new drugs due to its unique structure and reactivity.
Used in Agrochemical Industry:
(1R,2R,3S,5R)-(2-AMINO-2,6,6-TRIMETHYL-BICYCLO[3.1.1]HEPT-3-YL)-METHANOL is also utilized as a building block in the synthesis of agrochemicals, playing a role in the development of effective and innovative products for agricultural applications.
Used as a Chiral Auxiliary:
(1R,2R,3S,5R)-(2-AMINO-2,6,6-TRIMETHYL-BICYCLO[3.1.1]HEPT-3-YL)-METHANOL serves as a chiral auxiliary in asymmetric synthesis, a technique crucial for producing enantiomerically pure compounds, which is essential in many chemical and pharmaceutical processes.
Used in Medicinal Chemistry Research:
Due to its potential biological activity, (1R,2R,3S,5R)-(2-AMINO-2,6,6-TRIMETHYL-BICYCLO[3.1.1]HEPT-3-YL)-METHANOL is employed in medicinal chemistry research to explore and develop new drugs, further expanding its applications in the field of pharmaceuticals.

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-/m0/s1

Upstream product

• 7785-26-4 (-)-α-pinene 
• 705949-02-6 C₁₂H₂₁NO₂ 
• 328010-06-6 (1R,2R,5S,7R)-2,8,8-trimethyl-3-azatricyclo[5.1.1.0^2,5]nonan-4-one 
• 327611-75-6 ethyl (1R,2R,3S,5R)-2-amino-2,6,6-trimethylbicyclo[3.1.1]heptane-3-carboxylate 

Downstream Products

• 327611-80-3 1-((1R,2R,3S,5R)-3-Hydroxymethyl-2,6,6-trimethyl-bicyclo[3.1.1]hept-2-yl)-3-phenyl-thiourea 

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 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 and Cytoselective toxicity of Monoterpene-fused 2-Imino-1,3-Thiazines

Starting from pinane-, apopinane- and carane-based 1,3-amino alcohols obtained from monoterpene-based ?-amino acids, a library of monoterpene-fused 2-imino-1,3-Thiazines as main products and 2-Thioxo-1,3-oxazines as side-products were prepared via two- or

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-