721884-82-8

Basic information

• Product Name: (1R,3R)-3-AMINO-CYCLOHEXANOL
• Synonyms: (1R,3R)-3-AMINO-CYCLOHEXANOL;Cyclohexanol, 3-amino-, (1R,3R)-;(1R,3R)-3-aminocyclohexan-1-ol;(1R,3R)-3-Aminocyclohexan-1-ol hydrochloride;(1R,3R)-3-Aminocyclohexanol(WX600038)
• CAS NO: 721884-82-8
• Molecular Formula: C₆H₁₃NO
• Molecular Weight: 115.17
• Mol File: 721884-82-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (1R,3R)-3-AMINO-CYCLOHEXANOL(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,3R)-3-AMINO-CYCLOHEXANOL(721884-82-8)
• EPA Substance Registry System: (1R,3R)-3-AMINO-CYCLOHEXANOL(721884-82-8)

Safety Data

• Hazardous Substances Data: 721884-82-8(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
(1R,3R)-3-AMINO-CYCLOHEXANOL is used as a building block in organic synthesis for the creation of various chemical compounds. Its cyclohexane ring and amine group provide a foundation for the development of new molecules with specific functionalities.
Used as a Chiral Auxiliary in Asymmetric Reactions:
In the field of asymmetric synthesis, (1R,3R)-3-AMINO-CYCLOHEXANOL serves as a chiral auxiliary, helping to control the stereochemistry of reactions and enabling the production of enantiomerically pure compounds. This is crucial for the synthesis of biologically active molecules with desired properties.
Used in Pharmaceutical Research for Drug Development:
(1R,3R)-3-AMINO-CYCLOHEXANOL is utilized in pharmaceutical research as a key intermediate for the development of new drugs. Its unique structure and properties make it a promising candidate for the design and synthesis of novel therapeutic agents with potential applications in medicine.
Used in Materials Science:
In materials science, (1R,3R)-3-AMINO-CYCLOHEXANOL can be employed in the development of new materials with specific properties, such as chiral polymers or self-assembling systems. Its cyclohexane ring and amine group contribute to the creation of materials with unique characteristics for various applications.

Upstream product

• 6850-39-1 (+/-)-trans-3-aminocyclohexanol 
• 13941-94-1 (rac)-trans-1-(3-hydroxycyclohexyl)benzamide 
• 13941-94-1 (R,R)-3-benzylamidocyclohexanol 
• 6850-39-1 3-aminocyclohexanol 
• 721884-88-4 (R,R)-3-benzylaminocyclohexanol 
• 750649-39-9 ((1R,3R)-3-hydroxycyclohexyl)carbamic acid benzyl ester 
• 106729-79-7 (+/-)-cis-2-(3-hydroxycyclohexyl)isoindole-1,3-dione 
• 750649-42-4 acetic acid (1R,3R)-3-(benzyloxycarbonylamino)cyclohexyl ester 
• 750649-39-9 (+/-)-trans-(3-hydroxycyclohexyl)carbamic acid benzyl ester 

Downstream Products

• 1315499-76-3 C₁₉H₂₀N₄O₅S 
• 1315497-35-8 (1R,3R)-3-(5-Amino-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-ylamino)cyclohexanol 
• 1315497-36-9 (1R,3R)-3-(2-methyl-6-(phenylsulfonyl)imidazo[4,5-d]pyrrolo[2,3-b]pyridin-1(6H)-yl)cyclohexanol 
• 1418002-96-6 (1R,3R)-3-(3-nitro-[1,5]naphthyridin-4-ylamino)-cyclohexanol 
• 1397342-59-4 (1R,3R)-3-(5,5,6,6-Tetramethyl-4,4-dioxo-5,6-dihydro-4H-4λ6-[1,4,3]oxathiazin-2-ylamino)cyclohexanol 
• 1315499-77-4 C₂₂H₂₄N₄O₄S 
• 1315491-19-0 (1R,3R)-3-(2-((R)-1-hydroxyethyl)imidazo[4,5-d]pyrrolo[2,3-b]pyridin-1(6H)-yl)cyclohexanol 
• 1418002-17-1 C₁₆H₁₈N₄O 
• 1418002-97-7 (1R,3R)-3-(3-amino-[1,5]naphthyridin-4-ylamino)-cyclohexanol 

Relevant articles and documents

Asymmetric Phase-Transfer Catalytic aza-Michael Addition to Cyclic Enone: Highly Enantioselective and Diastereoselective Synthesis of Cyclic 1,3-Aminoalcohols

The highly enantioselective aza-Michael reaction of tert-butyl β-naphthylmethoxycarbamate to cyclic enones has been accomplished by using a new cinchona alkaloid derived C(9)-urea ammonium catalyst under phase-transfer catalysis conditions with up to 98% ee at 0 °C. The resulting aza-Michael adducts can be converted to versatile intermediates by selective deprotection and the cyclic 1,3-aminoalcohols by diastereoselective reduction with up to 32:1, which have been widely used as important pharmacophores in pharmaceutical development.

Resolution of N-protected cis- and trans-3-aminocyclohexanols via lipase-catalyzed enantioselective acylation in organic media

The enzymatic acylation of N-protected cis-and trans-1,3-aminocyclohexanols using lipases in organic solvents is described. By modifying certain reaction parameters such as the solvent, the lipase and the N-protecting group, it is possible to achieve high enantioselectivities and to obtain enantiomerically pure 3-aminocyclohexanols. The influence of the N-protecting group and the conformation of the substrate on the reaction rate was also studied.

Resolution of trans-3-aminocyclohexanol

(R,R)- and (S,S)-trans-3-Aminocyclohexanol were prepared via an enzymatic resolution of (±)-trans-1-acetoxy-3-benzylamido-cyclohexane with >95% enantiomeric excess.