189101-43-7

Basic information

• Product Name: Cyclohexanecarboxylic acid, 2-amino-, (1R,2S)- (9CI)
• Synonyms: Cyclohexanecarboxylic acid, 2-amino-, (1R,2S)- (9CI);2-Amino-(1R,2S)-cyclohexanecarboxylic acid;2-Amino-(1R-cis)-cyclohexanecarboxylic acid
• CAS NO: 189101-43-7
• Molecular Formula: C₇H₁₃NO₂
• Molecular Weight: 143.18362
• Product Categories: AMINOACID
• Mol File: 189101-43-7.mol

Chemical Properties

• Melting Point: 229-231℃
• Appearance: /
• CAS DataBase Reference: Cyclohexanecarboxylic acid, 2-amino-, (1R,2S)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclohexanecarboxylic acid, 2-amino-, (1R,2S)- (9CI)(189101-43-7)
• EPA Substance Registry System: Cyclohexanecarboxylic acid, 2-amino-, (1R,2S)- (9CI)(189101-43-7)

Safety Data

• Hazardous Substances Data: 189101-43-7(Hazardous Substances Data)

Upstream product

• 202867-96-7 2-benzyloxycarbonylamino-cyclohexanecarboxylic acid 
• 5691-20-3 (1RS,2SR)-2-aminocyclohexanecarboxylic acid 
• 22031-53-4 cis-2-aza-3-oxobicyclo<4.2.0>octane 
• 823190-77-8 (4aR,8aS)-3-[(S)-α-methylbenzyl]-1,2,4a,5,6,7,8,8a-octahydroquinazolin-4-one 
• 118-48-9 isatoic anhydride 
• 783371-72-2 2-amino-N-[(S)-α-methylbenzyl]-benzamide 
• 170623-28-6 3,4-dihydro-3-[(S)-α-methylbenzyl]-4-quinazolinone 
• 88335-92-6 (1S,2R)-2-(methoxycarbonyl)cyclohexanecarboxylic acid 
• 202867-95-6 (1R,2S)-2-Benzyloxycarbonylamino-cyclohexane-1-carboxylic acid methyl ester 

Downstream Products

• 202868-04-0 (1R,2S)-2-[(R)-2-(Benzyloxycarbonyl-methyl-amino)-3-phenyl-propionylamino]-cyclohexanecarboxylic acid 
• 158414-45-0 (1S,2R)-2-aminocyclohexanecarboxylic acid hydrochloride 
• 202868-07-3 ((R)-1-{(1S,2R)-2-[(S)-1-(Benzyloxycarbonylamino-imino-methyl)-2-oxo-piperidin-3-ylcarbamoyl]-cyclohexylcarbamoyl}-2-phenyl-ethyl)-methyl-carbamic acid benzyl ester 
• 202868-09-5 C₃₉H₄₈N₆O₇ 
• 837359-97-4 (1R,2S)-2-amino-cyclohexanecarboxylic acid methyl ester 
• 1417737-70-2 (1R,2S)-ethyl 2-[[(8-hydroxy-5-nitroquinolin-7-yl)methyl]amino]cyclohexanecarboxylate 

Relevant articles and documents

Enantiomeric discrimination of cyclic β-amino acids using (18-crown-6)-2,3,11,12-tetracarboxylic acid as a chiral NMR solvating agent

(18-Crown-6)-2,3,11,12-tetracarboxylic acid is an excellent chiral NMR solvating agent for cyclic β-amino acids with cyclopentane, cyclohexane, cycloheptane, cyclopentene, cyclohexene, bicyclo[2.2.1]heptane, and bicyclo[2.2.1]heptene rings. The crown ether was added to the neutral β-amino acids in methanol-d4. A neutralization reaction between the crown ether and β-amino acid forms the ammonium ion needed for favorable association. Enantiomeric discrimination of the two hydrogen atoms α to the amine and carboxylic acid moieties of the β-amino acid was observed with every substrate studied. Trends in the order of the enantiomeric discrimination of certain hydrogen atoms for substrates of similar structures correlate with the absolute configuration.

PEPTIDES AND PEPTIDOMIMETIC COMPOUNDS, THE MANUFACTURING THEREOF AS WELL AS THEIR USE FOR PREPARING A THERAPEUTICALLY AND/OR PREVENTIVELY ACTIVE PHARMACEUTICAL COMPOSITION

Peptides, peptidomimetics and derivatives thereof of the general formula I: H2N-GHRPX1-β-X4X5X6X7X8X9X10-X11 (I), in which X1-X10 denote one of the 20 genetically coded amino acids, wherein X8, X9 and X10 may also denote a single chemical bond;X11 denotes OR1 in which R1 equals hydrogen or (C1-C10) alkyl NR2R3 with R2 and R3 are equal or different and denote hydrogen, (C1-C10) alkyl, or a residue —W-PEG5-60K, in which the PEG residue is attached via a suitable spacer W to the N-atom, ora residue NH—Y-Z-PEG5-60K, in whichY denotes a chemical bond or a genetically coded amino acids from the group S, C, K or R andZ denotes a spacer, via which a polyethylene glycol (PEG)-residue can be attached, and their physiologically acceptable salts, andβ denotes an amino acid, or a peptidomimetic element, which induces a bend or turn in the peptide backbone.

Vapour-assisted enzymatic hydrolysis of β-lactams in a solvent-free system

A new, solvent-free, vapour-assisted method, developed for the synthesis of carbocyclic cis β-amino acid enantiomers through the Candida antarctica lipase B-catalysed enantioselective (E >200) hydrolysis of β-lactams with 0.5 equiv of H2O at 70 °C, has been demonstrated to be applicable on a preparative scale to produce (±)-2 (the starting racemate for cispentacin), (±)-3 (the starting racemate for 4-tert-butylcispentacin, a new cispentacin analogue) and (±)-7 (the starting racemate for 1,4-ethylene-bridged cispentacin).

Synthesis of enantiopure cis- and trans-2-aminocyclohexane-1-carboxylic acids from octahydroquinazolin-4-ones

The chemoselective and diastereoselective hydrogenation of 2,3-dihydro-3-[(S)-α-methylbenzyl]-4-quinazolinone 2 affords octahydroquinazolinones cis-3 and cis-4. Epimerization of cis-3 and cis-4 using t-BuO-K+ produces trans-5 and tra

Lipase-catalyzed enantioselective ring opening of unactivated alicyclic-fused beta-lactams in an organic solvent.

[reaction: see text] A highly efficient and very simple method was developed for the synthesis of enantiopure beta-amino acids (e.g. cispentacin) and beta-lactams through the enzyme-catalyzed enantioselective ring opening of unactivated alicyclic beta-lac

Enzymatic resolution of alicyclic β-lactams

Racemates of N-hydroxymethylated β-lactams 4-6 were resolved through the lipase-catalyzed asymmetric acylation of the primary hydroxy group at the 6S stereogenic centre. High enantioselectivity (E>200) was observed when the enzymatic reactions were perfor

Application of a new chiral stationary phase containing the glycopeptide antibiotic A-40,926 in the direct chromatographic resolution of β-amino acids

A new enantioselective HPLC procedure for the direct resolution of β-amino acids is described, based on the use of a new chiral stationary phase (CSP) containing the macrocyclic glycopeptide antibiotic A-40,926, structurally related to teicoplanin, covalently bonded to silica gel microparticles. The new CSP shows higher enantioselectivity and broader applicability in this field compared to the parent teicoplanin phase. The potential for semi-preparative separations on the A-40,926-CSP is demonstrated for a selected cyclic β-amino acid. Copyright (C) 2000 Elsevier Science Ltd.

1, 2-Disubstituted cyclohexane derived tripeptide aldehydes as novel selective thrombin inhibitors

A series of tripeptide arginine aldehydes was synthesized by replacement of proline with 1,2-disubstituted cyclohexane derivatives in the sequence of D-MePhe-Pro-Arg-H. Based on molecular modeling, further modification of the D-MePhe residue resulted in a potent and selective thrombin inhibitor.