64869-66-5

Basic information

• Product Name: (1R,3R)-1-amino-3-methylcyclohexane
• Synonyms: (1R,3R)-1-amino-3-methylcyclohexane
• CAS NO: 64869-66-5
• Molecular Weight: 113.203
• Mol File: 64869-66-5.mol

Chemical Properties

• CAS DataBase Reference: (1R,3R)-1-amino-3-methylcyclohexane(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,3R)-1-amino-3-methylcyclohexane(64869-66-5)
• EPA Substance Registry System: (1R,3R)-1-amino-3-methylcyclohexane(64869-66-5)

Safety Data

• Hazardous Substances Data: 64869-66-5(Hazardous Substances Data)

Upstream product

• 13368-65-5 (3R)-3-methylcyclohexanone 
• 89-82-7 pulegone 
• 64825-78-1 5-methyl-5-hexen-1-al 
• 1193-18-6 3-methylcyclohexen-2-one 
• 24965-91-1 cis-3-methylcyclohexanol 
• 591-24-2 3-Methylcyclohexanone 

Downstream Products

• 2523-64-0 (1R)-trans-dimethylamino-1-methyl-cyclohexane 
• 90204-18-5 (1R)-trans-3-formylamino-1-methyl-cyclohexane 
• 854428-32-3 (1R)-trans-3-butyrylamino-1-methyl-cyclohexane 

Relevant articles and documents

Synthesis of (1R,3R)-1-amino-3-methylcyclohexane by an enzyme cascade reaction

Amine transaminases (ATAs) are powerful enzymes for the synthesis of chiral amines. Although the request for amines with more than one chiral center is increasing, their synthesis is still challenging. Here we show a casacde reaction combining an enoate r

Expedient Synthesis of Bridged Bicyclic Nitrogen Scaffolds via Orthogonal Tandem Catalysis

Bridged nitrogen bicyclic skeletons have been accessed via unprecedented site- and diastereoselective orthogonal tandem catalysis from readily accessible reactants in a step economic manner. Directed Pd-catalyzed γ-C(sp3)-H olefination of aminocyclohexane with gem-dibromoalkenes, followed by a consecutive intramolecular Cu-catalyzed amidation of the 1-bromo-1-alkenylated product delivers the interesting normorphan skeleton. The tandem protocol can be applied on substituted aminocyclohexanes and aminoheterocycles, easily providing access to the corresponding substituted, aza- and oxa-analogues. The Cu catalyst of the Ullmann-Goldberg reaction additionally avoids off-cycle Pd catalyst scavenging by alkenylated reaction product. The picolinamide directing group stabilizes the enamine of the 7-alkylidenenormorphan, allowing further product post functionalizations. Without Cu catalyst, regio- and diastereoselective Pd-catalyzed γ-C(sp3)-H olefination is achieved.

Two subtle amino acid changes in a transaminase substantially enhance or invert enantiopreference in cascade syntheses

Amine transaminases (ATAs) are powerful enzymes for the stereospecific production of chiral amines. However, the synthesis of amines incorporating more than one stereocenter is still a challenge. We developed a cascade synthesis to access optically active

Biomimetic Polyene Cyclizations. Asymmetric Induction during the Acid-Catalyzed Cyclization of Chiral Imines

This paper reports the details of a basic study showing that an imino function is suitable to initiate acid-catalyzed cyclizations of polyenes, affording high yields of cyclized products.The additional advantage of such a function is to introduce very easily a chirality on the polyene skeleton by the way of a chiral group linked to nitrogen.The extent of asymmetric induction by a chiral phenethyl group on nitrogen is from 36percent to 65percent, according to the monocyclic or bicyclic nature of the substrate.