37982-23-3

Basic information

• Product Name: (+)-(1S,2R)-2-Phenylcyclohexanamine
• Synonyms: (+)-(1S,2R)-2-Phenylcyclohexanamine
• CAS NO: 37982-23-3
• Molecular Weight: 175.274
• Mol File: 37982-23-3.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: (+)-(1S,2R)-2-Phenylcyclohexanamine(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-(1S,2R)-2-Phenylcyclohexanamine(37982-23-3)
• EPA Substance Registry System: (+)-(1S,2R)-2-Phenylcyclohexanamine(37982-23-3)

Safety Data

• Hazardous Substances Data: 37982-23-3(Hazardous Substances Data)

Upstream product

• 34713-97-8 (+/-)-trans-2-phenyl-cyclohexanecarbonyl chloride 
• 25022-23-5 phenyl-1 aza-7 bicyclo<4.1.0>heptane 
• 1444-65-1 (RS)-2-phenylcyclohexanone 
• 93-92-5 1-phenylethyl acetate 
• 6290-49-9 methyl methoxyacetate 
• 1011-11-6 trans-2-phenylcyclohexylamine 
• 771-98-2 1-Phenylcyclohexene 
• 286-20-4 cyclohexane-1,2-epoxide 
• 2362-61-0 trans-2-Phenylcyclohexanol 
• 5670-71-3 1-nitro-2-phenylcyclohex-1-ene 
• 2362-61-0 cis-2-phenylcyclohexanol 
• 22591-17-9 2-phenylcyclohexanone oxime 
• 56923-15-0 1-hydroxyimino-2-phenyl-2-cyclohexene 
• 100-58-3 phenylmagnesium bromide 

Downstream Products

• 92321-01-2 trans-1-(N,N-dimethylamino)-2-phenylcyclohexane 
• 92321-01-2 cis-1-(N,N-dimethylamino)-2-phenylcyclohexane 
• 966-89-2 (+/-)-N-(trans-2-phenyl-cyclohexyl)-benzamide 
• 82771-32-2 C₂₄H₃₃N₃O₄S₂ 
• 69743-67-5 (1R,2S)-trans-2-phenylcyclohexylamine 
• 312611-48-6 (1R,2S)-N-(2-phenylcyclohexyl)acetamide 
• 37982-29-9 (1S,2S)-(+)-cis-2-Phenyl-cyclohexanamin 
• 37982-28-8 (1R,2R)-(-)-cis-2-Phenyl-cyclohexanamin 
• 121841-17-6 1R,2R-cis-N-Acetyl-2-phenylcyclohexanamin 
• 121841-18-7 1S,2S-cis-N-Acetyl-2-phenylcyclohexanamin 
• 70113-90-5 (1S,2R)-N-(2-phenylcyclohexyl)acetamide 
• 101427-67-2 (+/-)-N,N-dimethyl-N'-(trans-2-phenyl-cyclohexyl)-ethylenediamine 
• 107151-59-7 (+/-)-N,N-dimethyl-glycine-(trans-2-phenyl-cyclohexylamide) 
• 102753-41-3 (+/-)-N-benzyl-N',N'-dimethyl-N-(trans-2-phenyl-cyclohexyl)-ethylenediamine 

Relevant articles and documents

Nickel-Catalyzed Dearomative trans -1,2-Carboamination

We describe the development of an arenophile-mediated, nickel-catalyzed dearomative trans-1,2-carboamination protocol. A range of readily available aromatic compounds was converted to the corresponding dienes using Grignard reagents as nucleophiles. This strategy provided products with exclusive trans-selectivity and high enantioselectivity was observed in case of benzene and naphthalene. The utility of this methodology was showcased by controlled and stereoselective preparation of small, functionalized molecules.

METAL CATALYZED DEAROMATIVE 1,2-CARBOAMINATION

Described herein is the development of an arenophile-mediated, nickel-catalyzed dearomative trans-1,2-carboamination protocol. A range of readily available aromatic compounds was converted to the corresponding dienes using Grignard reagents as nucleophiles. This strategy provided products with exclusive trans-selectivity and high enantioselectivity was observed in case of benzene and naphthalene. The utility of this methodology was showcased by controlled and stereoselective preparation of small, functionalized molecules. A concise synthesis of (+)-pancratistatin and (+)-7-deoxypancratistatin from benzene using an enantioselective, dearomative carboamination strategy has been achieved. This approach, in combination with the judicious choice of subsequent olefin-type difunctionalization reactions, permits rapid and controlled access to a hexasubstituted core. Finally, minimal use of intermediary steps as well as direct, late stage C-7 hydroxylation provides both natural products in six and seven operations.

Enantioselective acylation of rac-2-phenylcycloalkanamines catalyzed by lipases

The kinetic resolution of some 2-phenylcycloalkanamines was performed by means of aminolysis reactions catalyzed by lipases, with Kazlauskas' rule being obeyed in all cases. The size of the ring and the stereochemistry of the stereogenic centers of the amines had a strong influence on both the enantiomeric ratio and the reaction rate of these aminolysis processes. Lipase B from Candida antarctica (CAL-B) showed excellent enantioselectivities toward trans-2-phenylcyclohexanamine in a variety of reaction conditions (E >150), whereas lipase A from C. antarctica (CAL-A) was the best catalyst for the acylation of cis-2-phenylcyclohexanamine (E = 34) and trans-2- phenylcyclopropanamine (E = 9).