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49805-30-3

Basic Information
CAS No.: 49805-30-3
Name: 2-Azabicyclo[2.2.1]hept-5-en-3-one
Molecular Structure:
Molecular Structure of 49805-30-3 (2-Azabicyclo[2.2.1]hept-5-en-3-one)
Formula: C6H7NO
Molecular Weight: 109.13
Synonyms: (+/-)-2-Azabicyclo[2.2.1]hept-5-en-3-one;Vince lactam;
EINECS: 421-830-3
Density: 1.198 g/cm3
Melting Point: 54-58 °C(lit.)
Boiling Point: 319.3 °C at 760 mmHg
Flash Point: 167.1 °C
Solubility: >1000 g/L (23 °C) in water
Appearance: solid
Hazard Symbols: IrritantXi, HarmfulXn
Risk Codes: 36/37/38-43-22
Safety: 26-36-36/37
Transport Information:
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With hydrogen; palladium on activated charcoal In ethyl acetate99%
With palladium 10% on activated carbon; hydrogen In ethyl acetate99%
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
ConditionsYield
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%
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With hydrogenchloride95%
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
ConditionsYield
With hydrogenchloride In methanol; toluene94.4%
With hydrogenchloride In methanol94.9%
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With tetra-(n-butyl)ammonium iodide; sodium hydride In N,N-dimethyl-formamide91%
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
ConditionsYield
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
ConditionsYield
With dmap In tetrahydrofuran91%
With dmap In tetrahydrofuran91%
With dmap In tetrahydrofuran91%
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With sulfuric acid In methanol85.8%
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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%
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    Azabicyclo

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    zabicyclo [Alias]: 2-azabicyclo [2.2.1] hept-5-ene-3-one [CAS No.]: 49805-30-3 [Formula]: C6H7NO [Molecular Weight]: 109.13 [Appearance]: white to pale yellow crystals [Content]: ≥97.0% [Purity]: ≥99.0% Specification: 25 kg / barrel,

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

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    Product Description Product website: http://www.finerchem.com Product Name (+/-)-2-Azabicyclo[2.2.1]hept-5-en-3-one CAS No. 49805-30-3

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

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    2-Azabicyclo[2.2.1]hept-5-en-3-one Basic information Product Name: 2-Azabicyclo[2.2.1]hept-5-en-3-one Synonyms: 4-Amino-2-cyclopentene-1-carboxylic acid;4-AMINO-2-CYCLOPENTENE-1-CARBOXYL

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    Product name: Vince Lactam(2-Azabicyclo[2.2.1]hept-5-en-3-one CAS No.:49805-30-3 Molecule Formula:C6H7NO Molecule Weight:109.13 Purity: 98.0% Package: 25kg/drum Description:White or off-white crystalline powder Manufacture Standards:E

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    2-Azabicyclo[2.2.1]hept-5-en-3-one Chemical Properties Melting point 54-58 °C(lit.) Boiling point 102-106 °C0.25 mm Hg(lit.) density 1.1143 (rough estimate) refractive index 1.5040 (estimate) Fp >230 °F storage temp

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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