2-Azabicyclo[2.2.1]hept-5-en-3-one supplier

Name
2-Azabicyclo[2.2.1]hept-5-en-3-one
EINECS 421-830-3
CAS No. 49805-30-3
Article Data17
CAS DataBase
Density 1.198 g/cm³
Solubility >1000 g/L (23 °C) in water
Melting Point 54-58 °C(lit.)
Formula C₆H₇NO
Boiling Point 319.3 °C at 760 mmHg
Molecular Weight 109.128
Flash Point 167.1 °C
Transport Information
Appearance solid
Safety 26-36-36/37
Risk Codes 36/37/38-43-22
Molecular Structure
Hazard Symbols Xi, Xn
Synonyms (+/-)-2-Azabicyclo[2.2.1]hept-5-en-3-one;Vince lactam;
PSA 29.10000
LogP 0.38970

Synthetic route

: 542-92-7
cyclopenta-1,3-diene

: 506-77-4
cyanogen chloride

: 49805-30-3
2-azabicyclo[2.2.1.]hept-5-en-3-one

Conditions

Conditions	Yield
With sodium hydroxide In methanol at 0 - 5℃; for 8h; pH=4 - 5; Diels-Alder Cycloaddition;	95%

: 19158-51-1
P-toluenesulfonyl cyanide

: 49805-30-3
2-azabicyclo[2.2.1.]hept-5-en-3-one

Conditions

Conditions	Yield
	79.3%

: 19158-51-1
P-toluenesulfonyl cyanide

: 542-92-7
cyclopenta-1,3-diene

: 49805-30-3
2-azabicyclo[2.2.1.]hept-5-en-3-one

Conditions

Conditions	Yield
With acetic acid In dichloromethane 1) 10 deg C, 3 h, 2) 20 deg C, 1 h;	56%
With oxonium Yield given. Multistep reaction;

: 1189-71-5
isocyanate de chlorosulfonyle

: 542-92-7
cyclopenta-1,3-diene

A: 97911-48-3, 138127-85-2, 146864-12-2, 63838-48-2
(+/-)-6-azabicyclo[3.2.0]hept-3-en-7-one

B: 49805-30-3
2-azabicyclo[2.2.1.]hept-5-en-3-one

C: (+/-)-2,4-diazabicyclo[4.3.0]non-8-ene-3,5-dione

Conditions

Conditions	Yield
Stage #1: isocyanate de chlorosulfonyle; cyclopenta-1,3-diene In diethyl ether at -60℃; for 2h; Stage #2: With potassium hydroxide; sodium sulfite In diethyl ether at 0℃; for 0.5h;	A 46% B n/a C n/a

...Expand

: 1189-71-5
isocyanate de chlorosulfonyle

: 542-92-7
cyclopenta-1,3-diene

: 49805-30-3
2-azabicyclo[2.2.1.]hept-5-en-3-one

Conditions

Conditions	Yield
With sodium thiosulfate Yield given;
In dichloromethane at 20℃; for 0.166667h;

: 3-(Methanesulfonyl)-2-azabicyclo<2.2.1>hepta-2,5-diene

: 49805-30-3
2-azabicyclo[2.2.1.]hept-5-en-3-one

Conditions

Conditions	Yield
With acetic acid In dichloromethane for 1h; Ambient temperature; Yield given;
With acetic acid In dichloromethane for 1h; Mechanism; Ambient temperature;

: (1S,4R)-1-(2-Aza-bicyclo[2.2.1]hepta-2,5-diene-3-sulfonylmethyl)-7,7-dimethyl-bicyclo[2.2.1]heptan-2-one

: 49805-30-3
2-azabicyclo[2.2.1.]hept-5-en-3-one

Conditions

Conditions	Yield
With acetic acid Yield given;

: 49805-27-8
3-tosyl-2-azabicyclo [2.2.1]hepta-2,5-diene

: 49805-30-3
2-azabicyclo[2.2.1.]hept-5-en-3-one

Conditions

Conditions	Yield
With acetic acid

: 24224-99-5
benzenesulfonyl cyanide

: 542-92-7
cyclopenta-1,3-diene

: 49805-30-3
2-azabicyclo[2.2.1.]hept-5-en-3-one

Conditions

Conditions	Yield
With l-menthol ethylaluminum dichloride; water 1.) CH2Cl2, -25 deg C, 24 h, 2. ) CH2Cl2; Yield given. Multistep reaction;

: 542-92-7
cyclopenta-1,3-diene

: 49805-30-3
2-azabicyclo[2.2.1.]hept-5-en-3-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: CH2Cl2 / 2 h / Ambient temperature 2: AcOH / CH2Cl2 / 1 h / Ambient temperature View Scheme

: 24225-08-9
methanesulfonyl cyanide

: 542-92-7
cyclopenta-1,3-diene

: 49805-30-3
2-azabicyclo[2.2.1.]hept-5-en-3-one

Conditions

Conditions	Yield
With acetic acid In dichloromethane; water

: 49805-30-3
2-azabicyclo[2.2.1.]hept-5-en-3-one

: 61865-62-1
(1S,4R)-4-aminocyclopent-2-enecarboxylic acid hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride; water at 20℃; for 24h;	100%
With hydrogenchloride In water for 1h; Heating;	90%

: 24424-99-5
di-tert-butyl dicarbonate

: 49805-30-3
2-azabicyclo[2.2.1.]hept-5-en-3-one

: 162427-15-8
3-oxo-2-aza-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid tert-butyl ester

Conditions

Conditions	Yield
With dmap; triethylamine In tetrahydrofuran at 20℃;	100%
With dmap; triethylamine In dichloromethane for 24h; Ambient temperature;	99%
With dmap; triethylamine In chloroform for 5h; Ambient temperature;	95%

: 603-33-8
triphenylbismuthane

: 49805-30-3
2-azabicyclo[2.2.1.]hept-5-en-3-one

: 186586-76-5
rel-(1S,4R)-2-phenyl-2-azabicyclo[2.2.1]hept-5-en-3-one

Conditions

Conditions	Yield
With copper diacetate; triethylamine In dichloromethane for 24h; Ambient temperature;	100%

: 49805-30-3
2-azabicyclo[2.2.1.]hept-5-en-3-one

: 24647-29-8
2-Azabicyclo[2.2.1]heptan-3-one

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethyl acetate	99%
With palladium 10% on activated carbon; hydrogen In ethyl acetate	99%
With hydrogen; palladium on activated charcoal In ethyl acetate at 20℃; under 2625.2 Torr;	97%
With hydrogen; palladium on activated charcoal In ethyl acetate under 760 Torr; Ambient temperature;

: 67-56-1
methanol

: 49805-30-3
2-azabicyclo[2.2.1.]hept-5-en-3-one

: 1694-92-4
2-Nitrobenzenesulfonyl chloride

: methyl 4-(2-nitrobenzenesulfonylamino)cyclopent-2-enecarboxylate

Conditions

Conditions	Yield
Stage #1: methanol; 2-azabicyclo[2.2.1.]hept-5-en-3-one With sulfuryl dichloride at 20℃; for 3h; Stage #2: 2-Nitrobenzenesulfonyl chloride With triethylamine In dichloromethane at 0℃; for 1.5h; Further stages.;	98%

...Expand

: 1809-20-7
diisopropyl hydrogenphosphonate

: 49805-30-3
2-azabicyclo[2.2.1.]hept-5-en-3-one

: 1417780-51-8
diisopropyl(3-oxo-2-azabicyclo[2.2.1]hept-5-en-2-yl)phosphonate

Conditions

Conditions	Yield
With copper diacetate; potassium carbonate In toluene at 80℃; under 760.051 Torr; for 0.666667h; Reagent/catalyst; Molecular sieve;	97%

: 132151-65-6
(E)-3-methoxy-2-methylacryloyl isocyanate

: 49805-30-3
2-azabicyclo[2.2.1.]hept-5-en-3-one

: 136994-68-8
2--2-azabicyclo<2.2.1>hept-5-en-3-one

Conditions

Conditions	Yield
In benzene at 50℃; for 5h;	96%

: 100-39-0
benzyl bromide

: 49805-30-3
2-azabicyclo[2.2.1.]hept-5-en-3-one

: (1SR,4RS)-2-benzyl-2-azabicyclo[2.2.1]hept-5-en-3-one

Conditions

Conditions	Yield
Stage #1: 2-azabicyclo[2.2.1.]hept-5-en-3-one With potassium hydroxide In dimethyl sulfoxide at 20℃; for 0.5h; Stage #2: With tetra-(n-butyl)ammonium iodide In dimethyl sulfoxide for 0.25h; Stage #3: benzyl bromide In dimethyl sulfoxide at 0 - 20℃;	96%

: 67-56-1
methanol

: 49805-30-3
2-azabicyclo[2.2.1.]hept-5-en-3-one

: methyl 4-aminocyclopent-2-ene-1-carboxylate Hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride	95%

: 49805-30-3
2-azabicyclo[2.2.1.]hept-5-en-3-one

: 229613-83-6
(–)-methyl (1S,4R)-4-aminocyclopent-2-ene-1-carboxylate hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In methanol; toluene	94.4%
With hydrogenchloride In methanol	94.9%

: 49805-30-3
2-azabicyclo[2.2.1.]hept-5-en-3-one

: 98-80-6
phenylboronic acid

: 186586-76-5
rel-(1S,4R)-2-phenyl-2-azabicyclo[2.2.1]hept-5-en-3-one

Conditions

Conditions	Yield
With copper diacetate; triethylamine In acetonitrile at 20℃; for 36h; Reflux;	92%
With copper diacetate; triethylamine In dichloromethane for 64h; Ambient temperature;	12%

: 18742-02-4
2-bromo-2-(2-ethyl)dioxolane

: 49805-30-3
2-azabicyclo[2.2.1.]hept-5-en-3-one

: 1023307-00-7
2-(2-[1,3]dioxolan-2-yl-ethyl)-2-aza-bicyclo[2.2.1]hept-5-en-3-one

Conditions

Conditions	Yield
Stage #1: 2-azabicyclo[2.2.1.]hept-5-en-3-one With potassium hydroxide; benzyltriethylammonium bromide; potassium carbonate In acetonitrile at 20℃; for 0.0833333h; Stage #2: 2-bromo-2-(2-ethyl)dioxolane In acetonitrile for 1h; Heating; Further stages.;	92%

: 49805-30-3
2-azabicyclo[2.2.1.]hept-5-en-3-one

: 824-94-2
p-methoxybenzyl chloride

: 133636-61-0
2-(4'-methoxybenzyl)-2-azabicyclo<2.2.1>hept-5-en-3-one

Conditions

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; sodium hydride In N,N-dimethyl-formamide	91%
With tetra-(n-butyl)ammonium iodide; lithium hexamethyldisilazane In tetrahydrofuran; N,N-dimethyl-formamide -78 deg C to r.t.;	66%
With tetra-(n-butyl)ammonium iodide; lithium hexamethyldisilazane 1) THF, -78 deg C, 30 min, 2a) DMF, -78 to RT, 2b) RT, 24h; Yield given. Multistep reaction;

: 49805-30-3
2-azabicyclo[2.2.1.]hept-5-en-3-one

: 77745-22-3
exo-cis-5,6-Dihydroxy-2-azabicyclo<2.2.1>heptan-3-one

Conditions

Conditions	Yield
With potassium permanganate In water; acetone for 1h; Ambient temperature;	91%

: 34619-03-9
tert-butyldicarbonate

: 49805-30-3
2-azabicyclo[2.2.1.]hept-5-en-3-one

: 162427-15-8
3-oxo-2-aza-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid tert-butyl ester

Conditions

Conditions	Yield
With dmap In tetrahydrofuran	91%
With dmap In tetrahydrofuran	91%
With dmap In tetrahydrofuran	91%

: 67-56-1
methanol

: 49805-30-3
2-azabicyclo[2.2.1.]hept-5-en-3-one

: 77745-25-6
cis-4-amino-2-cyclopentenecarboxylic acid methyl ester hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride for 22h; Heating;	89%

: 49805-30-3
2-azabicyclo[2.2.1.]hept-5-en-3-one

: 74-88-4
methyl iodide

: (1SR,4RS)-2-methyl-2-azabicyclo[2.2.1]hept-5-en-3-one

Conditions

Conditions	Yield
Stage #1: 2-azabicyclo[2.2.1.]hept-5-en-3-one With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Stage #2: methyl iodide In tetrahydrofuran; mineral oil at 20℃; for 72h; Inert atmosphere;	87%

: 49805-30-3
2-azabicyclo[2.2.1.]hept-5-en-3-one

: cis-4-amino-2-cyclopentene-1-carboxylic acid methyl ester hydrogen sulfate

Conditions

Conditions	Yield
With sulfuric acid In methanol	85.8%

: 1692-25-7
3-pyridylboronic acid

: 49805-30-3
2-azabicyclo[2.2.1.]hept-5-en-3-one

: 1236057-45-6
rel-(1S,4R)-2-(pyridin-3-yl)-2-azabicyclo[2.2.1]hept-5-en-3-one

Conditions

Conditions	Yield
With trimethylamine-N-oxide; copper diacetate; potassium hydroxide In acetonitrile at 20 - 80℃; Microwave irradiation;	85%

: 49805-30-3
2-azabicyclo[2.2.1.]hept-5-en-3-one

: 1694-92-4
2-Nitrobenzenesulfonyl chloride

: 191467-21-7
2-(2-Nitro-benzenesulfonyl)-2-aza-bicyclo[2.2.1]hept-5-en-3-one

Conditions

Conditions	Yield
With n-butyllithium In tetrahydrofuran at -78℃;	83%

: 10365-98-7
3-methoxyphenylboronic acid

: 49805-30-3
2-azabicyclo[2.2.1.]hept-5-en-3-one

: 1070242-17-9
rel-(1S,4R)-2-(3-methoxyphenyl)-2-azabicyclo[2.2.1]hept-5-en-3-one

Conditions

Conditions	Yield
With trimethylamine-N-oxide; copper diacetate; potassium hydroxide In acetonitrile at 20 - 80℃; Microwave irradiation;	83%

: 591-18-4
1-Bromo-3-iodobenzene

: 49805-30-3
2-azabicyclo[2.2.1.]hept-5-en-3-one

: 2-(3-bromophenyl)-2-aza-bicyclo[2.2.1]hept-5-en-3-one

Conditions

Conditions	Yield
With Al2O3#dotCu(2+); potassium carbonate In N,N-dimethyl-formamide at 110℃; for 16h; Inert atmosphere;	82%

: 49805-30-3
2-azabicyclo[2.2.1.]hept-5-en-3-one

: 106-96-7
propargyl bromide

: 1023306-62-8
2-prop-2-ynyl-2-azabicyclo[2.2.1]hept-5-en-3-one

Conditions

Conditions	Yield
Stage #1: 2-azabicyclo[2.2.1.]hept-5-en-3-one With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: propargyl bromide In N,N-dimethyl-formamide at 20℃; for 1h; Further stages.;	81%

: 49805-30-3
2-azabicyclo[2.2.1.]hept-5-en-3-one

: 127801-86-9, 137038-08-5
(1RS,2SR,4RS,5SR)-3-oxa-6-azatricyclo[3.2.1.02,4]octan-7-one

Conditions

Conditions	Yield
With potassium hydroxide; oxone In methanol; water for 5h; Ambient temperature; pH 6;	80%
With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 48h; Ambient temperature;	59%

: 49805-30-3
2-azabicyclo[2.2.1.]hept-5-en-3-one

: 444120-91-6
6-chloropyridin-3-ylboronic acid

: 1236057-46-7
rel-(1S,4R)-2-(6-chloropyridin-3-yl)-2-azabicyclo[2.2.1]hept-5-en-3-one

Conditions

Conditions	Yield
With trimethylamine-N-oxide; copper diacetate; potassium hydroxide In acetonitrile at 20 - 80℃; Microwave irradiation;	80%

: tributylsulfoammonium betaine

: 49805-30-3
2-azabicyclo[2.2.1.]hept-5-en-3-one

: C6H7NO4S*C12H27N

Conditions

Conditions	Yield
In acetonitrile at 30℃; for 24h; Inert atmosphere;	80%

: 49805-30-3
2-azabicyclo[2.2.1.]hept-5-en-3-one

: 7154-66-7
2-bromobenzoic acid chloride

: 2-(2-bromo-benzoyl)-2-aza-bicyclo[2.2.1]hept-5-en-3-one

Conditions

Conditions	Yield
Stage #1: 2-azabicyclo[2.2.1.]hept-5-en-3-one With sodium hydride In tetrahydrofuran at 20℃; for 0.75h; Stage #2: 2-bromobenzoic acid chloride In tetrahydrofuran at 20℃;	79%

2-Azabicyclo[2.2.1]hept-5-en-3-one Specification

The Vince Lactam is an organic compound with the formula C₆H₇NO. The IUPAC name of this chemical is 2-azabicyclo[2.2.1]hept-5-en-3-onato(2-). With the CAS registry number 49805-30-3, it is also named as 4-Amino-2-cyclopentene-1-carboxylic acid lactam. The product's categories are (Intermediate of Abacavir); Heterocycles; Intermediates; Fused Ring Systems; Cyanogen Chloride Derivatives; Hydrocyanic Acid Derivatives. Besides, it should be stored in a closed cool and dry place. It is used as a pharmaceutical intermediate.

Physical properties about Vince Lactam are: (1)ACD/LogP: -1.22; (2)ACD/LogD (pH 5.5): -1.22; (3)ACD/LogD (pH 7.4): -1.22; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 5.18; (7)ACD/KOC (pH 7.4): 5.18; (8)#H bond acceptors: 2; (9)#H bond donors: 1; (10)Polar Surface Area: 20.31 Å²; (11)Index of Refraction: 1.545; (12)Molar Refractivity: 28.8 cm³; (13)Molar Volume: 91 cm³; (14)Polarizability: 11.41×10^-24cm³; (15)Surface Tension: 39.4 dyne/cm; (16)Density: 1.198 g/cm³; (17)Flash Point: 167.1 °C; (18)Enthalpy of Vaporization: 56.09 kJ/mol; (19)Boiling Point: 319.3 °C at 760 mmHg; (20)Vapour Pressure: 0.000342 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
It is harmful if swallowed and may cause sensitisation by skin contact. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, this chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing and gloves.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C1NC2\C=C/C1C2
(2)InChI: InChI=1/C6H7NO/c8-6-4-1-2-5(3-4)7-6/h1-2,4-5H,3H2,(H,7,8)
(3)InChIKey: DDUFYKNOXPZZIW-UHFFFAOYAJ
(4)Std. InChI: InChI=1S/C6H7NO/c8-6-4-1-2-5(3-4)7-6/h1-2,4-5H,3H2,(H,7,8)
(5)Std. InChIKey: DDUFYKNOXPZZIW-UHFFFAOYSA-N

Product Name

2-Azabicyclo[2.2.1]hept-5-en-3-one

Synthetic route

2-Azabicyclo[2.2.1]hept-5-en-3-one Specification

Related Products

Hot Products