5992-23-4

Basic information

• Product Name: 4α-Phenyl-1α-aminocyclohexane
• Synonyms: 4α-Phenyl-1α-aminocyclohexane;cis-4-Phenyl-cyclohexylamine
• CAS NO: 5992-23-4
• Molecular Formula: C₁₂H₁₇N
• Molecular Weight: 175.27
• Mol File: 5992-23-4.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4α-Phenyl-1α-aminocyclohexane(CAS DataBase Reference)
• NIST Chemistry Reference: 4α-Phenyl-1α-aminocyclohexane(5992-23-4)
• EPA Substance Registry System: 4α-Phenyl-1α-aminocyclohexane(5992-23-4)

Safety Data

• Hazardous Substances Data: 5992-23-4(Hazardous Substances Data)

Upstream product

• 4500-20-3 4-phenylcyclohexanone oxime 
• 4894-75-1 1-phenyl-4-cyclohexanone 
• 494861-71-1 C₂₅H₂₇N 
• 67498-85-5 cis-N-benzyl-4-phenylcyclohexan-1-amine 

Downstream Products

• 4754-30-7 N-<4-Chlor-benzolsulfonyl>-N'-<4c-phenyl-cyclohexyl>-harnstoff 
• 5769-12-0 cis-N-Acetylamino-4-phenyl-cyclohexan 
• 59182-73-9 N-(cis-4-Phenylcyclohexyl)-3,3-diphenylpropylamin 
• 46817-68-9 cis-N-Butyl-4-phenyl-cyclohexylamin 
• 28142-37-2 trans-N-Butyl-4-phenyl-cyclohexylamin 
• 28142-10-1 trans-N-Butyl-N-butyryl-4-phenyl-cyclohexylamin 
• 28125-28-2 trans-N,N-Dibutyl-4-phenyl-cyclohexylamin 
• 5769-28-8 N-<4-Amino-benzolsulfonyl>-N'-<4c-phenyl-cyclohexyl>-harnstoff 
• 28142-06-5 trans-N-Butyryl-4-phenyl-cyclohexylamin 
• 28142-07-6 cis-N-Butyryl-4-phenyl-cyclohexylamin 
• 28142-17-8 cis-N-<2-(4)-Biphenylyl-butyryl>-4-phenyl-cyclohexylamin 
• 59182-76-2 N-(cis-4-Phenylcyclohexyl)-3,3-diphenylpropionamid 
• 5769-19-7 N-<4-Methyl-benzolsulfonyl>-N'-<4c-phenyl-cyclohexyl>-harnstoff 

Relevant articles and documents

Application of Transaminases in a Disperse System for the Bioamination of Hydrophobic Substrates

The challenging bioamination of hydrophobic substrates has been attained through the employment of a disperse system consisting of a combination of a low polarity solvent (e. g. isooctane or methyl-tert-butylether), a non-ionic surfactant and a minimal amount of water. In these conditions, amine transaminases (ATA) were shown to efficiently carry out the reductive amination of variously substituted cyclohexanones, providing good conversions often coupled with a superior stereoselectivity if compared with the corresponding chemical reductive amination. An array of synthetically useful 4-substituted aminocyclohexanes was consequentially synthesized through biocatalysis, analyzed and stereochemically characterized. (Figure presented.).

Reductive amination of ketonic compounds catalyzed by Cp*Ir(III) complexes bearing a picolinamidato ligand

Cp*Ir complexes bearing a 2-picolinamide moiety serve as effective catalysts for the direct reductive amination of ketonic compounds to give primary amines under transfer hydrogenation conditions using ammonium formate as both the nitrogen and hydrogen source. The clean and operationally simple transformation proceeds with a substrate to catalyst molar ratio (S/C) of up to 20,000 at relatively low temperature and exhibits excellent chemoselectivity toward primary amines.

Synthesis, GluN2B affinity and selectivity of benzo[7]annulen-7-amines

Due to their beneficial side effect profile, NMDA receptor antagonists interacting selectively with the allosteric ifenprodil binding site of the GluN2B subunit are of major interest for the treatment of neurological and neurodegenerative disorders. A series of benzo[7]annulen-7-amines 6 was designed by conformational restriction of ifenprodil (1). At first the benzo[7]annulen-7-one 11 was prepared in a three-step synthesis comprising of a double Knoevenagel condensation of phthalaldehyde (7) with dimethyl 3-oxoglutarate (8), hydrogenation of 9 and saponification/decarboxylation of 10. Reductive amination of the ketone 11 with primary amines and NaBH(OAc)3 led to the secondary amines 6a-d, cis-6h and trans-6i. The tertiary amines 6e-g were obtained by SN2-substitution of the nosylate 13. Although H-bond forming substituents in 2- and 5-position are missing, the amines 6 exhibit high affinity towards GluN2B containing NMDA receptors. A distance of four to five bond lengths between the basic amino moiety and the phenyl ring in the side chain appears to be optimal for high GluN2B affinity. The phenylcyclohexylamine cis-6h and the 4-benzylpiperidine 6g show the highest GluN2B affinities (Ki = 2.3 nM and 2.9 nM, respectively). With respect to selectivity against the PCP binding site, σ1 and σ2 receptors the phenylpiperazine 6f is the most promising GluN2B antagonist.