(s)-3-Aminoazepan-2-one

Base Information

• Chemical Name: (s)-3-Aminoazepan-2-one
• CAS No.: 21568-87-6
• Molecular Formula: C6H12N2O
• Molecular Weight: 128.174
• Hs Code.: 2933790090
• European Community (EC) Number: 630-719-0
• DSSTox Substance ID: DTXSID60331504
• Nikkaji Number: J207.954B
• Wikidata: Q27102328
• Metabolomics Workbench ID: 50872
• ChEMBL ID: CHEMBL288850
• Mol file: 21568-87-6.mol

Synonyms:21568-87-6;(s)-3-aminoazepan-2-one;(3S)-3-aminoazepan-2-one;(S)-3-Amino-2-azepanone;(s)-alpha-amino-omega-caprolactam;(s)-3-amino-hexahydro-2-azepinone;L-2-aminohexano-6-lactam;(s)-3-amino-azepan-2-one;L-Lysine 1,6-lactam;(s)-(-)-alpha-amino-omega-caprolactam;l-Alpha-amino-epsilon-caprolactam;L-2-Amino-cycloheptalactam;2H-Azepin-2-one, 3-aminohexahydro-, (3S)-;L-alpha-aminocaprolactam;CHEBI:17342;(3~{s})-3-Azanylazepan-2-One;MFCD00064476;L-2-Amino-hexano-6-lactam;(S)-2-Aminohexano-6-lactam;L-Lysine lactam (hydrochloride);Lysine lactam, L-;(3S)-3-aminohexahydro-2H-azepin-2-one;l-alpha-amino-caprolactam;C02837;(S)-Amino-omega-caprolactam;CHEMBL288850;SCHEMBL1114446;DTXSID60331504;BOWUOGIPSRVRSJ-YFKPBYRVSA-N;(s)-3-aminohexahydro-2-azepinone;WAA56887;AKOS006345206;AKOS007930225;AC-1938;CS-W002297;L-(-)-alpha-amino-epsilon-caprolactam;(s)-3-aminohexahydro-2h-azepin-2-one;AM803517;AS-44384;BP-13062;A4636;A56020;EN300-113672;Q-103175;Q27102328;8F4

Chemical Property of (s)-3-Aminoazepan-2-one

Chemical Property:

• Vapor Pressure: 0.000446mmHg at 25°C
• Melting Point: 97-101 °C
• Refractive Index: 1.47
• Boiling Point: 315.124 °C at 760 mmHg
• PKA: 16.06±0.40(Predicted)
• Flash Point: 144.382 °C
• PSA: 55.12000
• Density: 1.031 g/cm³
• LogP: 0.64290
• Storage Temp.: −20°C
• Solubility.: Aqueous Acid (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 128.094963011
• Heavy Atom Count: 9
• Complexity: 114

Purity/Quality:

98% ^*data from raw suppliers

(S)-3-Amino-2-azepanone(>90%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCNC(=O)C(C1)N
• Isomeric SMILES: C1CCNC(=O)[C@H](C1)N
• Uses: (S)-3-Amino-2-azepanone is used as an intermediate in the synthesis of bengamide E analogs and capuramycin and its analogs as antibacterial agents.

Technology Process of (s)-3-Aminoazepan-2-one

There total 11 articles about (s)-3-Aminoazepan-2-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

L-Lysine hydrochloride (657-27-2,10098-89-2,26124-78-7) → 2-aminocaprolactam (21568-87-6)

Guidance literature:

With aluminum oxide; sodium hydroxide; In pentan-1-ol; at 137 ℃; for 4h; Product distribution / selectivity; Heating / reflux;

Reference yield: 95.0%

L-lysine (56-87-1,3506-25-0) → 2-aminocaprolactam (21568-87-6)

Guidance literature:

With chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane; In xylene;

DOI:10.1016/j.bmcl.2007.08.047

Reference yield: 45.0%

Isobengamide E (118477-05-7) + 2,2-dimethoxy-propane (77-76-9) → (6E)-6,7,8,9-tetradeoxy-8-methyl-2-O-methyl-3,5-O-(1-methylethylidene)gulonon-6-enonic acid lactone (118477-21-7) + (2R,3R)-3-[(4R,5R)-2,2-Dimethyl-5-((E)-3-methyl-but-1-enyl)-[1,3]dioxolan-4-yl]-3-hydroxy-2-methoxy-propionic acid (118477-19-3) + 2-aminocaprolactam (21568-87-6)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; for 24h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Ambient temperature;

DOI:10.1021/ja00184a037

upstream raw materials:

α-nitrocaprolactam

Isobengamide E

2,2-dimethoxy-propane

lysine methyl ester dihydrochloride

Downstream raw materials:

(S)-3-(formylamino)-ε-caprolactam

tert-butyl N-[(3S)-2-oxoazepan-3-yl]carbamate

Acetic acid (E)-(R)-1-{(4S,5R)-5-[(R)-methoxy-((S)-2-oxo-azepan-3-ylcarbamoyl)-methyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4-methyl-pent-2-enyl ester

(E)-(2R,3S,4S,5R)-3,4,5-Tris-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-8-methyl-non-6-enoic acid ((S)-2-oxo-azepan-3-yl)-amide