209983-91-5

Basic information

• Product Name: (S)-3-AMINO-1-BENZYL-AZEPAN-2-ONE
• Synonyms: L--Amino--N-benzyl-caprolactam;L-A-AMINO-E-N-BENZYL-CAPROLACTAM;L-alpha-Amino-epsilon-N-benzyl-caprolactam;REF DUPL: L-alpha-Amino-epsilon-N-benzyl-caprolactam;2H-Azepin-2-one, 3-aminohexahydro-1-(phenylmethyl)-, (3S)-;(3S)-3-Aminohexahydro-1-benzyl-2H-azepin-2-one;(3S)-3-Amino-1-benzyl-azepan-2-one
• CAS NO: 209983-91-5
• Molecular Formula: C₁₃H₁₈N₂O
• Molecular Weight: 218.29
• Mol File: 209983-91-5.mol

Chemical Properties

• Boiling Point: 405℃
• Flash Point: 199℃
• Appearance: /
• Density: 1.104
• Vapor Pressure: 9.35E-07mmHg at 25°C
• Refractive Index: 1.561
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (S)-3-AMINO-1-BENZYL-AZEPAN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-3-AMINO-1-BENZYL-AZEPAN-2-ONE(209983-91-5)
• EPA Substance Registry System: (S)-3-AMINO-1-BENZYL-AZEPAN-2-ONE(209983-91-5)

Safety Data

• Hazardous Substances Data: 209983-91-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Medicinal Chemistry:
(S)-3-AMINO-1-BENZYL-AZEPAN-2-ONE is used as a chemical intermediate for the synthesis of various pharmaceutical compounds. Its unique structure, including the presence of an amino group, a ketone group, and a benzyl group, allows it to participate in a wide range of chemical reactions, making it a valuable building block in the development of new drugs.
Used in Chemical Reactions:
(S)-3-AMINO-1-BENZYL-AZEPAN-2-ONE is used as a reactant in various chemical reactions due to its reactivity. The presence of the amino and ketone groups allows it to undergo reactions such as nucleophilic addition, reduction, and condensation, enabling the synthesis of a variety of organic compounds.
Used in Research and Development:
(S)-3-AMINO-1-BENZYL-AZEPAN-2-ONE is used as a research compound in the study of chemical reactions and the development of new synthetic methods. Its unique structure and reactivity make it an interesting subject for exploration in academic and industrial research settings.
Used in Chiral Chemistry:
(S)-3-AMINO-1-BENZYL-AZEPAN-2-ONE is used in chiral chemistry due to its chiral nature. The presence of a stereogenic center results in distinct 'right-handed' and 'left-handed' forms, which can exhibit different properties and reactivities. This makes it a valuable compound for studying the effects of chirality on chemical reactions and the development of enantioselective synthetic methods.

InChI:InChI=1/C13H18N2O/c14-12-8-4-5-9-15(13(12)16)10-11-6-2-1-3-7-11/h1-3,6-7,12H,4-5,8-10,14H2/t12-/m0/s1

Upstream product

• 56-87-1 L-lysine 
• 61071-66-7 2-[(3S)-2-oxoazepan-3-yl]isoindoline-1,3-dione 
• 21568-87-6 2-aminocaprolactam 
• 76944-95-1 tert-butyl N-[(3S)-2-oxoazepan-3-yl]carbamate 
• 100-39-0 benzyl bromide 
• 2389-45-9 Boc-Lys(Z)-OH 
• 1055423-27-2 (3S)-3-[[(1,1-dimethylethoxy)carbonyl]amino]hexahydro-2-oxo-1H-azepine-1-carboxylic acid phenylmethyl ester 
• 380629-65-2 (S)-1-benzyl-2-oxo-3-(tert-butoxycarbonylamino)-azepine 

Relevant articles and documents

Synthesis of bengamide E analogues and their cytotoxic activity

A series of bengamide E analogues were prepared from the corresponding polyketide chain and amino acids via amide coupling reactions. Opening of the polyketide chain lactone ring with α-aminolactams was successfully achieved under microwave irradiation in the presence of sodium 2-ethyl hexanoate. A cytotoxic activity evaluation against a panel of cancer cell lines (KB, HepG-2, Lu-1, MCF-7, HL-60 and Hela) indicated that the 2′R analogues were generally more cytotoxic than the 2′S analogues. Additionally, several analogues exhibited selective inhibition against various cancer cell lines: compounds 32a and 32b selectively inhibited MCF-7 cells, while 33b and 35b were more sensitive toward Lu-1 and HepG-2, respectively. Notably, some of the synthetic analogues possess cytotoxic activities with IC50 values less than 1?μM.

Stereochemical diversity in asymmetric cyclization via memory of chirality

An enantiodivergent asymmetric cyclization of N-Boc-N-ω-bromoalkyl-α-amino acid derivatives has been developed. With potassium amide bases in DMF, cyclization proceeds with retention of configuration, while inversion of configuration was observed with lit

Parallel liquid synthesis of N,N′-disubstituted 3-amino azepin-2-ones as potent and specific farnesyl transferase inhibitors

A rapid structure-activity study was performed by parallel liquid synthesis on N,N′-disubstitution of 3-amino azepin-2-one to afford potent and specific farnesyl transferase inhibitors with low nM enzymatic and cellular activities. The activities of the selected compounds were validated in vivo, and compounds 41a and 44a presented significant antitumour activity.