| Identification | Back Directory | [Name]
D-alpha-Amino-epsilon-caprolactam | [CAS]
28957-33-7 | [Synonyms]
D-Lysine lactam
(R)-3-AMinoazepane
(R)-3-Amino-2-azepanone
(3R)-3-aminoazepan-2-one
(R)-a-Amino-omega-caprolactam
(R)-3-Amino-Hexahydro-1H-Azepin
(R)-3-Aminohexahydro-1H-azepin-2-one
(3R)-3α-Aminohexahydro-1H-azepine-2-one
(3R)-3α-Aminohexahydro-2H-azepine-2-one
(2R)-2,6-Diaminohexanoic acid 1,6-lactam
[R,(+)]-3-Aminohexahydro-1H-azepin-2-one
2H-Azepin-2-one, 3-aminohexahydro-, (R)-
2H-Azepin-2-one, 3-aMinohexahydro-, (3R)- | [EINECS(EC#)]
674-645-7 | [Molecular Formula]
C6H12N2O | [MDL Number]
MFCD00010201 | [MOL File]
28957-33-7.mol | [Molecular Weight]
128.17 |
| Chemical Properties | Back Directory | [Melting point ]
97-101 °C | [Boiling point ]
315.1±35.0 °C(Predicted) | [density ]
1.031±0.06 g/cm3(Predicted) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2–8 °C | [solubility ]
DMF: 30 mg/ml,DMSO: 30 mg/ml,Ethanol: 30 mg/ml,PBS (pH 7.2): 10 mg/ml | [form ]
A neat oil | [pka]
16.06±0.40(Predicted) | [InChI]
InChI=1S/C6H12N2O/c7-5-3-1-2-4-8-6(5)9/h5H,1-4,7H2,(H,8,9)/t5-/m1/s1 | [InChIKey]
BOWUOGIPSRVRSJ-RXMQYKEDSA-N | [SMILES]
N1CCCC[C@@H](N)C1=O |
| Hazard Information | Back Directory | [Uses]
(S)-3-Amino-2-azepanone is a useful research chemical. It is used as an intermediate in the synthesis of bengamide E analogs and capuramycin and its analogs as antibacterial agents. (R)-3-Amino-2-azepanone is used as an intermediate for the synthesis of β-oxocarboxamides as antiviral agents. | [Definition]
ChEBI: D-2-aminohexano-6-lactam is a 2-aminohexano-6-lactam. It is a conjugate base of a D-2-ammoniohexano-6-lactam. It is an enantiomer of a L-2-aminohexano-6-lactam. | [Synthesis]
General procedure for the synthesis of (R)-3-amino-2-caprolactam from L-lysine hydrochloride: 30 g (164 mmol) of L-lysine hydrochloride and 150 mL of 1,2-propanediol as a solvent were added to a 250 mL three-neck flask. Under stirring conditions, 6.57 g of sodium hydroxide was slowly added with continuous stirring until complete dissolution. Subsequently, the reaction mixture was heated to reflux and the reflux reaction was maintained for 5 hours, during which time the water generated was removed by means of a water separator and the progress of the reaction was monitored by thin-layer chromatography (TLC) until the reaction was complete. Upon completion of the reaction, the mixture was cooled to room temperature and the by-product sodium chloride was removed by filtration. The filtrate was acidified dropwise by adding 6 mol/L aqueous hydrochloric acid to the filtrate, followed by a back-extraction operation. The aqueous phase was collected, dried over anhydrous sodium sulfate, and recrystallized by adding appropriate amount of ethanol to finally obtain 21.9 g of white solid product (R)-α-amino caprolactam in 81% yield. | [References]
[1] Patent: CN106946779, 2017, A. Location in patent: Paragraph 0031; 0033; 0034 |
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