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49805-30-3

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49805-30-3 Usage

Chemical Properties

solid

Uses

Different sources of media describe the Uses of 49805-30-3 differently. You can refer to the following data:
1. Intermediate for pharmaceuticals. Product Data Sheet
2. 2-Azabicyclo[2.2.1]hept-5-en-3-one was used in:preparation of (3aS,4R,6R,6aR)-6-((methoxy-methoxy)methyl)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-amine, a precursor of analog of bredininsynthesis of therapeutic drugschemoenzymatic synthesis of (?)-carbovir
3. Abacavir intermediate. 2-Azabicyclo[2.2.1]hept-5-en-3-one is used as an intermediate in the synthesis of carbocyclic sugar amines, carbanucleosides, and carbocyclic dinucleotide analogues.

General Description

2-Azabicyclo[2.2.1]hept-5-en-3-one is also referred as vince lactam. It is a versatile intermediate in the synthesis of carbocyclic nucleosides. 2-Azabicyclo[2.2.1]hept-5-en-3-one and its monohydrated complex was investigated in a supersonic jet by Fourier transform microwave spectroscopy.

Check Digit Verification of cas no

The CAS Registry Mumber 49805-30-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 4,9,8,0 and 5 respectively; the second part has 2 digits, 3 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 49805-30:
(7*4)+(6*9)+(5*8)+(4*0)+(3*5)+(2*3)+(1*0)=143
143 % 10 = 3
So 49805-30-3 is a valid CAS Registry Number.

49805-30-3 Well-known Company Product Price

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  • Aldrich

  • (331910)  2-Azabicyclo[2.2.1]hept-5-en-3-one  98%

  • 49805-30-3

  • 331910-1G

  • 1,013.22CNY

  • Detail
  • Aldrich

  • (331910)  2-Azabicyclo[2.2.1]hept-5-en-3-one  98%

  • 49805-30-3

  • 331910-5G

  • 2,877.03CNY

  • Detail

49805-30-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

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

1.2 Other means of identification

Product number -
Other names 2-Arabicyclo[2.2.1]hept-5-en-3-one

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:49805-30-3 SDS

49805-30-3Synthetic route

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

cyclopenta-1,3-diene

cyanogen chloride
506-77-4

cyanogen chloride

2-azabicyclo[2.2.1.]hept-5-en-3-one
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%
P-toluenesulfonyl cyanide
19158-51-1

P-toluenesulfonyl cyanide

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

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

Conditions
ConditionsYield
79.3%
P-toluenesulfonyl cyanide
19158-51-1

P-toluenesulfonyl cyanide

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

cyclopenta-1,3-diene

2-azabicyclo[2.2.1.]hept-5-en-3-one
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;
isocyanate de chlorosulfonyle
1189-71-5

isocyanate de chlorosulfonyle

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

cyclopenta-1,3-diene

A

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

(+/-)-6-azabicyclo[3.2.0]hept-3-en-7-one

B

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

(+/-)-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
isocyanate de chlorosulfonyle
1189-71-5

isocyanate de chlorosulfonyle

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

cyclopenta-1,3-diene

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

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

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

(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

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

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

Conditions
ConditionsYield
With acetic acid Yield given;
3-tosyl-2-azabicyclo [2.2.1]hepta-2,5-diene
49805-27-8

3-tosyl-2-azabicyclo [2.2.1]hepta-2,5-diene

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

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

Conditions
ConditionsYield
With acetic acid
benzenesulfonyl cyanide
24224-99-5

benzenesulfonyl cyanide

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

cyclopenta-1,3-diene

2-azabicyclo[2.2.1.]hept-5-en-3-one
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;
cyclopenta-1,3-diene
542-92-7

cyclopenta-1,3-diene

2-azabicyclo[2.2.1.]hept-5-en-3-one
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
methanesulfonyl cyanide
24225-08-9

methanesulfonyl cyanide

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

cyclopenta-1,3-diene

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

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

Conditions
ConditionsYield
With acetic acid In dichloromethane; water
2-azabicyclo[2.2.1.]hept-5-en-3-one
49805-30-3

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

(1S,4R)-4-aminocyclopent-2-enecarboxylic acid hydrochloride
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%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

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

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
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%
triphenylbismuthane
603-33-8

triphenylbismuthane

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

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

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

2-Azabicyclo[2.2.1]heptan-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;
methanol
67-56-1

methanol

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

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

2-Nitrobenzenesulfonyl chloride
1694-92-4

2-Nitrobenzenesulfonyl chloride

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

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%
diisopropyl hydrogenphosphonate
1809-20-7

diisopropyl hydrogenphosphonate

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

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

diisopropyl(3-oxo-2-azabicyclo[2.2.1]hept-5-en-2-yl)phosphonate
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%
(E)-3-methoxy-2-methylacryloyl isocyanate
132151-65-6

(E)-3-methoxy-2-methylacryloyl isocyanate

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

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

2--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%
benzyl bromide
100-39-0

benzyl bromide

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

(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%
methanol
67-56-1

methanol

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

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

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

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

Conditions
ConditionsYield
With hydrogenchloride95%
2-azabicyclo[2.2.1.]hept-5-en-3-one
49805-30-3

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

(–)-methyl (1S,4R)-4-aminocyclopent-2-ene-1-carboxylate hydrochloride
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%
2-azabicyclo[2.2.1.]hept-5-en-3-one
49805-30-3

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

phenylboronic acid
98-80-6

phenylboronic acid

rel-(1S,4R)-2-phenyl-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 acetonitrile at 20℃; for 36h; Reflux;92%
With copper diacetate; triethylamine In dichloromethane for 64h; Ambient temperature;12%
2-bromo-2-(2-ethyl)dioxolane
18742-02-4

2-bromo-2-(2-ethyl)dioxolane

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

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

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

p-methoxybenzyl chloride
824-94-2

p-methoxybenzyl chloride

2-(4'-methoxybenzyl)-2-azabicyclo<2.2.1>hept-5-en-3-one
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;
2-azabicyclo[2.2.1.]hept-5-en-3-one
49805-30-3

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

exo-cis-5,6-Dihydroxy-2-azabicyclo<2.2.1>heptan-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%
tert-butyldicarbonate
34619-03-9

tert-butyldicarbonate

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

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
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%
methanol
67-56-1

methanol

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

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

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

cis-4-amino-2-cyclopentenecarboxylic acid methyl ester hydrochloride

Conditions
ConditionsYield
With hydrogenchloride for 22h; Heating;89%
2-azabicyclo[2.2.1.]hept-5-en-3-one
49805-30-3

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

methyl iodide
74-88-4

methyl iodide

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

(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%
2-azabicyclo[2.2.1.]hept-5-en-3-one
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

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

Conditions
ConditionsYield
With sulfuric acid In methanol85.8%
3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

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

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

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

2-Nitrobenzenesulfonyl chloride
1694-92-4

2-Nitrobenzenesulfonyl chloride

2-(2-Nitro-benzenesulfonyl)-2-aza-bicyclo[2.2.1]hept-5-en-3-one
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%
3-methoxyphenylboronic acid
10365-98-7

3-methoxyphenylboronic acid

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

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

1-Bromo-3-iodobenzene

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

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

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

propargyl bromide
106-96-7

propargyl bromide

2-prop-2-ynyl-2-azabicyclo[2.2.1]hept-5-en-3-one
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%
2-azabicyclo[2.2.1.]hept-5-en-3-one
49805-30-3

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

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

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

6-chloropyridin-3-ylboronic acid

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

tributylsulfoammonium betaine

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

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

C6H7NO4S*C12H27N

C6H7NO4S*C12H27N

Conditions
ConditionsYield
In acetonitrile at 30℃; for 24h; Inert atmosphere;80%
2-azabicyclo[2.2.1.]hept-5-en-3-one
49805-30-3

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

2-bromobenzoic acid chloride
7154-66-7

2-bromobenzoic acid chloride

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

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%

49805-30-3Relevant articles and documents

Unusual mechanism of hydrolysis of the tosyl cyanide-cyclopentadiene adduct to the lactam 2-azabicyclo[2.2.1]hept-5-en-3-one

Morgan, Paul E.,McCague, Ray,Whiting, Andrew

, p. 1811 - 1812 (1996)

Hydrolysis of the cycloaddition product derived from tosyl cyanide and cyclopentadiene was investigated using 18O label incorporation experiments; thus, sulfonyl imine 2 was transformed into 18O labelled lactam 3 with 18O labelled acetic acid, which is consistent with the intervention of intermediate 6 during the hydrolysis.

Carbovir-related compounds and phosphonate analogues

Pham, Phuong-T.,Vince, Robert

, p. 779 - 791 (2007)

Detailed syntheses of carbovir-related cis-[2-(9H-Purin-9-yl)-3- cyclopentene]-1-methanols and phosphonates of selected analogues are presented. Our interest in this chemistry stems from antiviral activity shown by closely related compounds. Access to the key β-lactam was achieved by the reaction of monocyclopentadiene with chlorosulfonyl isocyanate at -78°C rather than at the reported1 ambient temperature, where only the less ring-strained and more stable γ-lactam is formed. Copyright Taylor & Francis Group, LLC.

Substituted cyclopentane and cyclopentene compounds useful as neuraminidase inhibitors

-

, (2008/06/13)

Compounds I-III wherein U is CH, O, or S; Z is mono- or di-substituted carbon; R is (CH2)nCO2H, (CH2)nSO3H, (CH2)nPO3H2, (CH2)nNO2, CH(SCH3)3, esters; R1 is H, hydroxyalkyl, aminoalkyl, alkoxyalkyl; RR1 is O; n is 0-4; R2, R3 is H, hydroxyalkyl, aminoalkyl, alkoxyalkyl, haloalkyl; R4 is (CH2)nOH, (CH2)nNH2, substituted alkyl were prepd. as neuraminidase inhibitors. Thus, (1R,3R,4R,1′S)-(?)-(1′-acetylamino-2 ′-ethyl)butyl-4-(aminoimino)methylaminocyclopentan-1-carboxylic acid was prepd. and tested in vitro as neuraminidase inhibitor (IC501μM).

Process for producing 2-azabicyclo[2.2.1]hept-5-en-3-one

-

, (2008/06/13)

2-Azabicyclo[2.2.1]hept-5-en-3-one is prepared by a process comprising: continuously mixing a substituted sulfonyl cyanide represented by formula (I): R—SO2CN??(I), wherein R represents an alkyl group or a phenyl group or a substituted phenyl group, with cyclopentadiene; and then continuously adding the resultant reaction solution to water or to a mixed solvent comprising water and a hydrocarbon solvent under the condition that the pH of the present reaction mixture ranges from 4 to 7.

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