(1S,4R)-2-Aza-bicyclo[2.2.1]hept-5-en-3-one

Product Name: (1S,4R)-2-Aza-bicyclo[2.2.1]hept-5-en-3-one
CAS No.: 130931-83-8
Chemical Name: (1S,4R)-2-Aza-bicyclo[2.2.1]hept-5-en-3-one
Synonyms: (+)-VINCE'S LACTAM;(1S)-(+)-2-AzabicycL;(+)-2-AZABICYCLO[2,2,1]HEPT-5-EN-3-ONE;(1S,4R)-3-azabicyclo[2.2.1]hept-5-en-2-one;(1R,4S)-3-Azabicyclo[2.2.1]hept-5-en-2-one;(1S)-(+)-2-AZABICYCLO[2.2.1]HEPT-5-EN-3-ONE;(1S,4R)-2-AZA-BICYCLO[2.2.1]HEPT-5-EN-3-ONE;2-Azabicyclo[2.2.1]hept-5-en-3-one,(1S,4R)-;(1S)-(+)-2-Azabicyclo[2.2.1]hept-5-en-3-one >=98%;(1S)-(+)-2-Azabicyclo[2.2.1]hept-5-en-3-one
CBNumber: CB4196945
Molecular Formula: C6H7NO
Formula Weight: 109.13
MOL File: 130931-83-8.mol

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(1S,4R)-2-Aza-bicyclo[2.2.1]hept-5-en-3-one Property

Melting point:: 94-97 °C(lit.)
Boiling point:: 319.3±0.0 °C(Predicted)
Density: 1.198±0.06 g/cm3(Predicted)
storage temp.: under inert gas (nitrogen or Argon) at 2-8°C
form: powder
pka: 15.48±0.20(Predicted)
color: Off-white
optical activity: [α]20/D +565°, c = 1 in chloroform
InChI: InChI=1S/C6H7NO/c8-6-4-1-2-5(3-4)7-6/h1-2,4-5H,3H2,(H,7,8)/t4-,5+/m0/s1
InChIKey: DDUFYKNOXPZZIW-CRCLSJGQSA-N
SMILES: [C@]12([H])C[C@]([H])(C=C1)C(=O)N2
CAS DataBase Reference: 130931-83-8(CAS DataBase Reference)

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Safety

Hazard Codes: Xi
Risk Statements: 36/37/38
Safety Statements: 26-36
WGK Germany: 3
HS Code: 2914290090

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 441287
Product name: (1S)-(+)-2-Azabicyclo[2.2.1]hept-5-en-3-one
Purity: ≥98%
Packaging: 1g
Price: $262
Updated: 2025/07/31

Sigma-Aldrich

Product number: 441287
Product name: (1S)-(+)-2-Azabicyclo[2.2.1]hept-5-en-3-one
Purity: ≥98%
Packaging: 5g
Price: $732
Updated: 2025/07/31

TRC

Product number: A965403
Product name: (1S,4R)-2-Aza-bicyclo[2.2.1]hept-5-en-3-one
Packaging: 50mg
Price: $45
Updated: 2021/12/16

Apolloscientific

Product number: OR315003
Product name: (1S)-(+)-2-Azabicyclo[2.2.1]hept-5-en-3-one
Packaging: 1g
Price: $53
Updated: 2021/12/16

ChemScene

Product number: CS-W001398
Product name: (1S,4R)-2-Azabicyclo[2.2.1]hept-5-en-3-one
Purity: >97.0%
Packaging: 5g
Price: $96
Updated: 2021/12/16

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(1S,4R)-2-Aza-bicyclo[2.2.1]hept-5-en-3-one Chemical Properties,Usage,Production

Chemical Properties

OFF-WHITE TO BEIGE CRYSTALLINE POWDER

Uses

This lactam and its antipode are precursors to the enantiomers of the carbocyclic nucleoside carbovir. It has been demonstrated that (-)-carbovir is a potent inhibitor of HIV-1 and based on clinical trials it could become an alternative to AZT. AZT is a trademark of The Wellcome Foundation Ltd.

Synthesis

157810-20-3

49805-30-3

GENERAL METHOD: Unreacted N-hydroxymethyl-γ-lactams (1S,4R)-1 and (1R,4S)-2 (20 mg, 0.14 mmol) were dissolved in methanol (2 mL). Subsequently, ammonium hydroxide (2 mL) was added and the reaction mixture was stirred at room temperature for 4 hours. Upon completion of the reaction, the solvent was removed by rotary evaporator and the residue was purified by silica gel column chromatography, using ethyl acetate as eluent, to afford white crystals of (1S,4R)-3 [15 mg, 95%; [α]D25 = +545 (c 0.3, CHCl3), ee = 99%; literature value 13: [α]D25 = +549 (c 0.26, CHCl3), ee > 99%; melting point 95-98°C (recrystallized from i-Pr2O), literature value 13: 97-100°C] or (1R,4S)-4 [15 mg, 93%; [α]D25 = +125.5 (c 0.55, CHCl3), ee = 96%; literature value 13: [α]D25 = +158 (c 0.45, CHCl3), ee > 99%; melting point 78-81°C (recrystallized from i-Pr2O), literature value 13: 78-81°C]. （1H NMR (400 MHz, CDCl3, 25 °C, TMS) data for (1S,4R)-3: δ = 2.18-2.43 (m, 2H, CH2); 3.18-3.24 (m, 1H, CHCO); 4.30-4.37 (m, 1H, CHNH); 6.05 (br s, 1H, NH); 6.63-6.82 ( m, 2H, CH=CH). Elemental analysis: calculated values (C6H7NO): C, 66.04; H, 6.47; N, 12.84; measured values: C, 66.12; H, 6.38; N, 12.82. 1H NMR (400 MHz, CDCl3, 25 °C, TMS) data for (1R,4S)-4: δ = 1.33-1.97 (m, 6H, 3 × CH2) ; 2.76-2.85 (m, 1H, CHCO); 3.04 (br s, 1H, NH); 3.95-4.08 (m, 1H, CHNH). Elemental analysis: calculated values (C6H9NO): C, 64.84; H, 8.16; N, 12.60; measured values: C, 64.81; H, 8.13; N, 12.68.

References

[1] Tetrahedron Asymmetry, 2016, vol. 27, # 16, p. 729 - 731
[2] Tetrahedron Asymmetry, 1996, vol. 7, # 8, p. 2381 - 2386
[3] Tetrahedron: Asymmetry, 1994, vol. 5, # 7, p. 1155 - 1156

(1S,4R)-2-Aza-bicyclo[2.2.1]hept-5-en-3-one Preparation Products And Raw materials

Raw materials

Preparation Products

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(1S,4R)-2-Aza-bicyclo[2.2.1]hept-5-en-3-one Suppliers

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View Lastest Price from (1S,4R)-2-Aza-bicyclo[2.2.1]hept-5-en-3-one manufacturers

Hefei Lbao Physical & Chemical Science Co.,Ltd

Product: (1S,4R)-2-Azabicyclo[2.2.1]hept-5-en-3-one 130931-83-8
Price: US $0.00/kg
Min. Order: 1kg
Purity: 98%
Supply Ability: Customise
Release date: 2025-11-28

Shaanxi Dideu New Materials Co. Ltd

Product: (1S,4R)-2-Aza-bicyclo[2.2.1]hept-5-en-3-one 130931-83-8
Price: US $0.00-0.00/KG
Min. Order: 1KG
Purity: 98.0%
Supply Ability: 10000KGS
Release date: 2025-05-19

Career Henan Chemical Co

Product: (1S,4R)-2-Aza-bicyclo[2.2.1]hept-5-en-3-one 130931-83-8
Price: US $1.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: Customized
Release date: 2018-12-19

130931-83-8, (1S,4R)-2-Aza-bicyclo[2.2.1]hept-5-en-3-oneRelated Search:

(1R,3S)-3-Aminocyclopentanecarboxylic acid 6-Methyl-5-hepten-2-one Dicyclopentadiene (+)-(1R,4S)-N-BOC-4-AMINOCYCLOPENT-2-ENECARBOXYLIC ACID (-)-(1R,3S)-N-Boc-3-Aminocyclopentanecarboxylic acid BOC-1,3-CIS-ACHC-OH (1R,2S)-cis-2-Aminocyclopentanol hydrochloride Cyclopentanamine, 3-fluoro-, hydrochloride (1:1), (1S,3R)- (1R,3R,5R)-2-(tert-Butoxycarbonyl)-2-azabicyclo[3.1.0]hexane-3-carboxylic acid CYCLOHEXANECARBOXYLIC ACID, 3-[[(1,1-DIMETHYLETHOXY)CARBONYL]AMINO]-, (1R,3S)- (1S,2R)-rel-2-(6-bromopyridin-3-yl)cyclopropan-1-amine dihydrochloride (1S,4R)-tert-butyl 3-oxo-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate 2-Azabicyclo[2.2.1]hept-5-en-3-one (6R,7S)-2-ACETYL-2-AZA-BICYCLO[2.2.1]HEPT-5-EN-3-ONE (1R,4S)-2-AZA-BICYCLO[2.2.1]HEPT-5-EN-3-ONE (6R,7S)-2-BOC-2-AZA-BICYCLO[2.2.1]HEPT-5-EN-3-ONE 2-Azabicyclo[2.2.1]hept-5-ene (1S,4R)-2-Aza-bicyclo[2.2.1]hept-5-en-3-one

(1S,4R)-2-AZA-BICYCLO[2.2.1]HEPT-5-EN-3-ONE

(1S)-(+)-2-AZABICYCLO[2.2.1]HEPT-5-EN-3-ONE

(1S)-(+)-2-AZABICYCLO(2.2.1)HEPT-5-EN-3- ONE, 98+% (99% EE/HPLC)

(+)-2-AZABICYCLO[2.2.1]HEPT-5-EN-3-ONE 98% 95+% E.E.

(+)-VINCE'S LACTAM

(1R,4S)-3-Azabicyclo[2.2.1]hept-5-en-2-one

2-Azabicyclo[2.2.1]hept-5-en-3-one,(1S,4R)-

(1S)-(+)-2-Azabicyclo[2.2.1]hept-5-en-3-one >=98%

(1S)-(+)-2-AzabicycL

(+)-2-AZABICYCLO[2,2,1]HEPT-5-EN-3-ONE

(1S,4R)-3-azabicyclo[2.2.1]hept-5-en-2-one

(+)-2-AZABICYCLO[2.2.1]HEPT-5-EN-3-ONE,98%,>9 5% EE

(1S,4R)-2-Azabicyclo[2.2.1]hept-5-en-3-one / (+)-Vince Lactam

(1<i>S</i>)-(+)-2-Azabicyclo[2.2.1]hept-5-en-3-one

130931-83-8

Lactams

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Chiral Building Blocks

Asymmetric Synthesis

Heterocycle-other series

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Lactams

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