488703-59-9

Basic information

• Product Name: (R,R)-2-Carbamoylcyclohexanecarboxylic acid
• Synonyms: (R,R)-2-Carbamoylcyclohexanecarboxylic acid;Cyclohexanecarboxylic acid, 2-(aminocarbonyl)-, (1R,2R)-
• CAS NO: 488703-59-9
• Molecular Formula: C₈H₁₃NO₃
• Molecular Weight: 171.19372
• Mol File: 488703-59-9.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R,R)-2-Carbamoylcyclohexanecarboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (R,R)-2-Carbamoylcyclohexanecarboxylic acid(488703-59-9)
• EPA Substance Registry System: (R,R)-2-Carbamoylcyclohexanecarboxylic acid(488703-59-9)

Safety Data

• Hazardous Substances Data: 488703-59-9(Hazardous Substances Data)

Usage

General Description

(R,R)-2-Carbamoylcyclohexanecarboxylic acid is a chemical compound with the molecular formula C9H15NO3. It is a carboxylic acid derivative that contains both a carbamoyl group and a cyclohexane ring. (R,R)-2-Carbamoylcyclohexanecarboxylic acid is commonly used as a chiral building block in organic synthesis, particularly in the production of pharmaceuticals and other bioactive molecules. Its unique structure and properties make it a valuable tool for creating complex molecular structures with specific stereochemical arrangements. Additionally, (R,R)-2-Carbamoylcyclohexanecarboxylic acid has potential applications in the development of new materials and chemical processes. Overall, this compound plays an important role in various areas of chemical research and development.

Upstream product

• 85-42-7 trans-1,2-cyclohexanedicarboxylic anhydride 

Downstream Products

• 389057-34-5 trans-(R,R)-2-aminocyclohexane carboxylic acid 
• 233661-54-6 (1R,2R)-2-((tert-butoxycarbonyl)amino)cyclohexane-1-carboxylic acid 
• 158414-45-0 (R,R)-trans-2-aminocyclohexanecarboxylic acid hydrochloride 

Relevant articles and documents

Enantiomerically pure β-amino acids: A convenient access to both enantiomers of trans-2-aminocyclohexanecarboxylic acid

Enantiomerically pure trans-2-aminocyclohexanecarboxylic acid is an important building block for helical β-peptides. We report here that this amino acid can be obtained from trans-cyclohexane-1,2-dicarboxylic acid in good yield by a simple one-pot procedure comprising cyclization to the anhydride, amide formation with ammonia, and a subsequent Hofmann-type degradation with phenyliodine(III) bis(trifluoroacetate) (PIFA) as the oxidant. The N-Fmoc- and N-BOC-protected derivatives were obtained by treatment of the amino acid with Fmoc-OSu and BOC2O, respectively. The N-BOC derivative could be prepared in even better overall yield by a one-pot procedure leading directly from trans-cyclohexane-1,2-dicarboxylic acid to the N-BOC-protected amino acid. Both enantiomers of the starting trans-1,2-cyclohexanedicarboxylic acid can be obtained easily and in large quantities by separating commercially available racemic trans-1,2-cyclohexanedicarboxylic acid using either (R)- or (S)-1-phenethylamine. X-ray crystallography of the diastereomerically pure salt obtained from (R)-1-phenethylamine revealed that the configuration of the diacid component is (1R,2R), and not (1S,2S) as reported in the literature. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.