cyclopenta-1,3-diene
cyanogen chloride
2-azabicyclo[2.2.1.]hept-5-en-3-one
Conditions | Yield |
---|---|
With sodium hydroxide In methanol at 0 - 5℃; for 8h; pH=4 - 5; Diels-Alder Cycloaddition; | 95% |
P-toluenesulfonyl cyanide
2-azabicyclo[2.2.1.]hept-5-en-3-one
Conditions | Yield |
---|---|
79.3% |
P-toluenesulfonyl cyanide
cyclopenta-1,3-diene
2-azabicyclo[2.2.1.]hept-5-en-3-one
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; |
isocyanate de chlorosulfonyle
cyclopenta-1,3-diene
A
(+/-)-6-azabicyclo[3.2.0]hept-3-en-7-one
B
2-azabicyclo[2.2.1.]hept-5-en-3-one
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 |
isocyanate de chlorosulfonyle
cyclopenta-1,3-diene
2-azabicyclo[2.2.1.]hept-5-en-3-one
Conditions | Yield |
---|---|
With sodium thiosulfate Yield given; | |
In dichloromethane at 20℃; for 0.166667h; |
2-azabicyclo[2.2.1.]hept-5-en-3-one
Conditions | Yield |
---|---|
With acetic acid In dichloromethane for 1h; Ambient temperature; Yield given; | |
With acetic acid In dichloromethane for 1h; Mechanism; Ambient temperature; |
2-azabicyclo[2.2.1.]hept-5-en-3-one
Conditions | Yield |
---|---|
With acetic acid Yield given; |
3-tosyl-2-azabicyclo [2.2.1]hepta-2,5-diene
2-azabicyclo[2.2.1.]hept-5-en-3-one
Conditions | Yield |
---|---|
With acetic acid |
benzenesulfonyl cyanide
cyclopenta-1,3-diene
2-azabicyclo[2.2.1.]hept-5-en-3-one
Conditions | Yield |
---|---|
With l-menthol ethylaluminum dichloride; water 1.) CH2Cl2, -25 deg C, 24 h, 2. ) CH2Cl2; Yield given. Multistep reaction; |
cyclopenta-1,3-diene
2-azabicyclo[2.2.1.]hept-5-en-3-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: CH2Cl2 / 2 h / Ambient temperature 2: AcOH / CH2Cl2 / 1 h / Ambient temperature View Scheme |
methanesulfonyl cyanide
cyclopenta-1,3-diene
2-azabicyclo[2.2.1.]hept-5-en-3-one
Conditions | Yield |
---|---|
With acetic acid In dichloromethane; water |
2-azabicyclo[2.2.1.]hept-5-en-3-one
(1S,4R)-4-aminocyclopent-2-enecarboxylic acid hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride; water at 20℃; for 24h; | 100% |
With hydrogenchloride In water for 1h; Heating; | 90% |
di-tert-butyl dicarbonate
2-azabicyclo[2.2.1.]hept-5-en-3-one
3-oxo-2-aza-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid tert-butyl ester
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% |
triphenylbismuthane
2-azabicyclo[2.2.1.]hept-5-en-3-one
rel-(1S,4R)-2-phenyl-2-azabicyclo[2.2.1]hept-5-en-3-one
Conditions | Yield |
---|---|
With copper diacetate; triethylamine In dichloromethane for 24h; Ambient temperature; | 100% |
2-azabicyclo[2.2.1.]hept-5-en-3-one
2-Azabicyclo[2.2.1]heptan-3-one
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; |
methanol
2-azabicyclo[2.2.1.]hept-5-en-3-one
2-Nitrobenzenesulfonyl chloride
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% |
diisopropyl hydrogenphosphonate
2-azabicyclo[2.2.1.]hept-5-en-3-one
diisopropyl(3-oxo-2-azabicyclo[2.2.1]hept-5-en-2-yl)phosphonate
Conditions | Yield |
---|---|
With copper diacetate; potassium carbonate In toluene at 80℃; under 760.051 Torr; for 0.666667h; Reagent/catalyst; Molecular sieve; | 97% |
(E)-3-methoxy-2-methylacryloyl isocyanate
2-azabicyclo[2.2.1.]hept-5-en-3-one
2--2-azabicyclo<2.2.1>hept-5-en-3-one
Conditions | Yield |
---|---|
In benzene at 50℃; for 5h; | 96% |
benzyl bromide
2-azabicyclo[2.2.1.]hept-5-en-3-one
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% |
methanol
2-azabicyclo[2.2.1.]hept-5-en-3-one
Conditions | Yield |
---|---|
With hydrogenchloride | 95% |
2-azabicyclo[2.2.1.]hept-5-en-3-one
(–)-methyl (1S,4R)-4-aminocyclopent-2-ene-1-carboxylate hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride In methanol; toluene | 94.4% |
With hydrogenchloride In methanol | 94.9% |
2-azabicyclo[2.2.1.]hept-5-en-3-one
phenylboronic acid
rel-(1S,4R)-2-phenyl-2-azabicyclo[2.2.1]hept-5-en-3-one
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% |
2-bromo-2-(2-ethyl)dioxolane
2-azabicyclo[2.2.1.]hept-5-en-3-one
2-(2-[1,3]dioxolan-2-yl-ethyl)-2-aza-bicyclo[2.2.1]hept-5-en-3-one
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% |
2-azabicyclo[2.2.1.]hept-5-en-3-one
p-methoxybenzyl chloride
2-(4'-methoxybenzyl)-2-azabicyclo<2.2.1>hept-5-en-3-one
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; |
2-azabicyclo[2.2.1.]hept-5-en-3-one
exo-cis-5,6-Dihydroxy-2-azabicyclo<2.2.1>heptan-3-one
Conditions | Yield |
---|---|
With potassium permanganate In water; acetone for 1h; Ambient temperature; | 91% |
tert-butyldicarbonate
2-azabicyclo[2.2.1.]hept-5-en-3-one
3-oxo-2-aza-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid tert-butyl ester
Conditions | Yield |
---|---|
With dmap In tetrahydrofuran | 91% |
With dmap In tetrahydrofuran | 91% |
With dmap In tetrahydrofuran | 91% |
methanol
2-azabicyclo[2.2.1.]hept-5-en-3-one
cis-4-amino-2-cyclopentenecarboxylic acid methyl ester hydrochloride
Conditions | Yield |
---|---|
With hydrogenchloride for 22h; Heating; | 89% |
2-azabicyclo[2.2.1.]hept-5-en-3-one
methyl iodide
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% |
2-azabicyclo[2.2.1.]hept-5-en-3-one
Conditions | Yield |
---|---|
With sulfuric acid In methanol | 85.8% |
3-pyridylboronic acid
2-azabicyclo[2.2.1.]hept-5-en-3-one
rel-(1S,4R)-2-(pyridin-3-yl)-2-azabicyclo[2.2.1]hept-5-en-3-one
Conditions | Yield |
---|---|
With trimethylamine-N-oxide; copper diacetate; potassium hydroxide In acetonitrile at 20 - 80℃; Microwave irradiation; | 85% |
2-azabicyclo[2.2.1.]hept-5-en-3-one
2-Nitrobenzenesulfonyl chloride
2-(2-Nitro-benzenesulfonyl)-2-aza-bicyclo[2.2.1]hept-5-en-3-one
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran at -78℃; | 83% |
3-methoxyphenylboronic acid
2-azabicyclo[2.2.1.]hept-5-en-3-one
rel-(1S,4R)-2-(3-methoxyphenyl)-2-azabicyclo[2.2.1]hept-5-en-3-one
Conditions | Yield |
---|---|
With trimethylamine-N-oxide; copper diacetate; potassium hydroxide In acetonitrile at 20 - 80℃; Microwave irradiation; | 83% |
1-Bromo-3-iodobenzene
2-azabicyclo[2.2.1.]hept-5-en-3-one
Conditions | Yield |
---|---|
With Al2O3#dotCu(2+); potassium carbonate In N,N-dimethyl-formamide at 110℃; for 16h; Inert atmosphere; | 82% |
2-azabicyclo[2.2.1.]hept-5-en-3-one
propargyl bromide
2-prop-2-ynyl-2-azabicyclo[2.2.1]hept-5-en-3-one
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% |
2-azabicyclo[2.2.1.]hept-5-en-3-one
(1RS,2SR,4RS,5SR)-3-oxa-6-azatricyclo[3.2.1.02,4]octan-7-one
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% |
2-azabicyclo[2.2.1.]hept-5-en-3-one
6-chloropyridin-3-ylboronic acid
rel-(1S,4R)-2-(6-chloropyridin-3-yl)-2-azabicyclo[2.2.1]hept-5-en-3-one
Conditions | Yield |
---|---|
With trimethylamine-N-oxide; copper diacetate; potassium hydroxide In acetonitrile at 20 - 80℃; Microwave irradiation; | 80% |
Conditions | Yield |
---|---|
In acetonitrile at 30℃; for 24h; Inert atmosphere; | 80% |
2-azabicyclo[2.2.1.]hept-5-en-3-one
2-bromobenzoic acid chloride
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% |
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
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