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

Name
(1S,4R)-2-Aza-bicyclo[2.2.1]hept-5-en-3-one
EINECS 421-830-3
CAS No. 130931-83-8
Article Data23
CAS DataBase
Density 1.199 g/cm³
Solubility
Melting Point 94-97 °C(lit.)
Formula C₆H₇NO
Boiling Point 319.302 °C at 760 mmHg
Molecular Weight 109.128
Flash Point 167.131 °C
Transport Information
Appearance off-white to beige crystalline powder
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 2-Azabicyclo[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;(1S,4R)-(+)-2-Azabicyclo[2.2.1]hept-5-en-3-one;(1S,4R)-2-Azabicyclo[2.2.1]hept-5-en-3-one;
PSA 29.10000
LogP 0.38970

Synthetic route

: 157810-20-3
(1S,4R)-N-hydroxymethyl-2-azabicyclo<2.2.1>hept-5-en-3-one

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

Conditions

Conditions	Yield
With ammonium hydroxide In methanol at 20℃; for 4h;	95%
With ammonium hydroxide In methanol for 12h; Ambient temperature;	45%
With methanol; ammonium hydroxide for 13h; Ambient temperature;	38%

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

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

Conditions

Conditions	Yield
With resin-supported recombinant Candida antarctica lipase B; water In tert-butyl methyl ether at 60℃; for 102h; enantioselective reaction;	48%
With citrophilla (ATCC No.21285) In phosphate buffer for 24h; pH=7.5;	31.8%
With lipase B Candida antarctica recombined fromAspergillus oryzae In aq. phosphate buffer for 168h; Reagent/catalyst; Enzymatic reaction;	n/a
Multi-step reaction with 3 steps 1: Sonication 2: water; lipase B from Candida antarctica; benzylamine / isopropyl alcohol / 0.5 h / 60 °C / Enzymatic reaction 3: ammonium hydroxide / methanol / 4 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1: Sonication 2: water; lipase B from Candida antarctica; benzylamine / isopropyl alcohol / 2 h / 60 °C / Enzymatic reaction 3: ammonium hydroxide / methanol / 4 h / 20 °C View Scheme

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

A: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

B: 102579-71-5, 102579-72-6, 102679-78-7, 134003-04-6, 134234-04-1
(-)-(1S, 4R)-4-amino-2-cyclopentene-1-carboxylic acid

Conditions

Conditions	Yield
With lipase B from Candida antarctica In water; isopropyl alcohol at 60℃; for 4h; Enzymatic reaction; stereospecific reaction;	A 46% B 48%
With water In tert-butyl methyl ether Enzymatic reaction; optical yield given as %ee;

: 169104-33-0
(1S,4R)-2-[(4-methoxyphenyl)methyl]-2-azabicyclo[2.2.1]hept-5-en-3-one

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

Conditions

Conditions	Yield
With ammonium cerium(IV) nitrate In water; acetonitrile at 0℃; for 2.5h;	26%

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

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

: (1R,6S)-6-Chlorocarbonyl-cyclohex-3-enecarboxylic acid isopropyl ester

A: 88586-06-5
(3aS,7aR)-3a,4,7,7a-tetrahydroisobenzofuran-1(3H)-one

B: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

Conditions

Conditions	Yield
With sodium tetrahydroborate; camphor-10-sulfonic acid 1.) THF, EtOH, -40 degC, 3 h; 2.) toluene, reflux, 5 h; Yield given. Multistep reaction;

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

A: 79200-56-9
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one

B: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

Conditions

Conditions	Yield
With brucine In methanol at 20℃; for 6h;
With Methylobacterium sp. Y1-6 at 30℃; for 24h; Overall yield = 19 %Chromat.;	A n/a B n/a
With malonamidase E2 (MAE2) In aq. phosphate buffer at 30℃; for 24h; pH=7.5; Resolution of racemate; Enzymatic reaction;	A n/a B n/a
With Cu-(R)-2,2'-dihydroxy-1,1'-binaphthalene-6,6'-dicarboxylic acid organic framework silica composite In ethanol; hexane Resolution of racemate;

: 157732-10-0
2-hydroxymethyl-2-azabicyclo<2.2.1>hept-5-en-3-one

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 2: 45 percent / aq. NH3 / methanol / 12 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 2: 38 percent / Nh4OH, MeOH / 13 h / Ambient temperature View Scheme

: 181136-52-7
(1S,6R)-6-(isopropoxycarbonyl)cyclohex-3-enecarboxylic acid

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: CH2Cl2 / 3 h / Ambient temperature 2: 1.) NaBH4; 2.) camphorsulfonic acid / 1.) THF, EtOH, -40 degC, 3 h; 2.) toluene, reflux, 5 h View Scheme

: 935-79-5
cis-1,2,3,6-tetrahydrophthalic anhydride

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) TADDOL / 1.) Et2O, r.t., 3 h; 2.) THF, -20 degC, 10 d 2: CH2Cl2 / 3 h / Ambient temperature 3: 1.) NaBH4; 2.) camphorsulfonic acid / 1.) THF, EtOH, -40 degC, 3 h; 2.) toluene, reflux, 5 h View Scheme

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

A: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

B: 102579-71-5, 102579-72-6, 102679-78-7, 134003-04-6, 134234-04-1
(-)-(1S, 4R)-4-amino-2-cyclopentene-1-carboxylic acid

Conditions

Conditions	Yield
With water In tert-butyl methyl ether Enzymatic reaction; optical yield given as %ee; enantioselective reaction;
With Bradyrhizobium japonicum USDA 6 (−)-γ-lactamase In aq. buffer at 50℃; pH=6; Kinetics; Temperature; pH-value; Concentration; Enzymatic reaction; enantioselective reaction;	A n/a B n/a
With cyclic imide hydrolase(CIH) In aq. phosphate buffer at 30℃; for 24h; pH=7.5; Resolution of racemate; Enzymatic reaction;	A n/a B n/a

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

A: 79200-56-9
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one

B: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

C: 134003-04-6
(1R,4S)-4-aminocyclopenten-2-ene-1-carboxylic acid

Conditions

Conditions	Yield
With Nocardia farcinica-polyamidase (NfpolyA) In aq. phosphate buffer at 30℃; for 24h; pH=7.5; Resolution of racemate; Enzymatic reaction;	A n/a B n/a C n/a

...Expand

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

A: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

B: 134003-04-6
(1R,4S)-4-aminocyclopenten-2-ene-1-carboxylic acid

C: 102579-71-5, 102579-72-6, 102679-78-7, 134003-04-6, 134234-04-1
(-)-(1S, 4R)-4-amino-2-cyclopentene-1-carboxylic acid

Conditions

Conditions	Yield
With non-heme chloroperoxidase (CPO-T) In aq. phosphate buffer at 30℃; for 24h; pH=7.5; Resolution of racemate; Enzymatic reaction;	A n/a B n/a C n/a

...Expand

: racemic N-hydroxymethyl vince lactam

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: water; lipase B from Candida antarctica; benzylamine / isopropyl alcohol / 0.5 h / 60 °C / Enzymatic reaction 2: ammonium hydroxide / methanol / 4 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: water; lipase B from Candida antarctica; benzylamine / isopropyl alcohol / 2 h / 60 °C / Enzymatic reaction 2: ammonium hydroxide / methanol / 4 h / 20 °C View Scheme

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

A: 79200-56-9
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one

B: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

C: 102579-71-5, 102579-72-6, 102679-78-7, 134003-04-6, 134234-04-1
(-)-(1S, 4R)-4-amino-2-cyclopentene-1-carboxylic acid

Conditions

Conditions	Yield
With water; lipase B from Candida antarctica In isopropyl alcohol at 60℃; for 0.5h; Enzymatic reaction;	A n/a B n/a C n/a

...Expand

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

: C6H9NO2

B: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

Conditions

Conditions	Yield
With chloroperoxidase In aq. phosphate buffer at 30℃; for 0.5h; pH=7; Kinetics; Reagent/catalyst; Temperature; Solvent; pH-value; Resolution of racemate; Green chemistry; Enzymatic reaction; enantioselective reaction;	A n/a B 2.1 g

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

: C6H9NO2

B: 79200-56-9
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one

C: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

Conditions

Conditions	Yield
With CfGL2 In aq. phosphate buffer at 30℃; for 9h; pH=7; Resolution of racemate; Green chemistry; Enzymatic reaction; enantioselective reaction;	A n/a B n/a C n/a

...Expand

: (1S,4R)-4-aminocyclopent-2-ene-1-carboxylic acid methyl ester tartrate

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine; methanol; lithium hydroxide; water / -20 °C / pH 6 - 7 2: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 18 h / 45 °C View Scheme

: 102579-71-5, 102579-72-6, 102679-78-7, 134003-04-6, 134234-04-1
(-)-(1S, 4R)-4-amino-2-cyclopentene-1-carboxylic acid

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

Conditions

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate In N,N-dimethyl-formamide at 45℃; for 18h;	n/a

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

A: 79200-56-9
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one

B: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

: 102579-71-5, 102579-72-6, 102679-78-7, 134003-04-6, 134234-04-1
cis-4-amino-cyclopent-2-ene-1-carboxylic acid

Conditions

Conditions	Yield
With (+) γ-lactamase immobilized on epoxy graphene oxide carrier In aq. phosphate buffer at 80℃; pH=8; Kinetics; Reagent/catalyst; Enzymatic reaction;

...Expand

: 3-((2S,5R)-2-Isopropyl-5-methyl-cyclohexanesulfonyl)-2-aza-bicyclo[2.2.1]hepta-2,5-diene

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

Conditions

Conditions	Yield
With sodium hydroxide In water; acetic acid

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

: 134003-02-4
(-)-2-Azabicyclo<2.2.1>heptan-3-one

Conditions

Conditions	Yield
With hydrogen; palladium 10% on activated carbon In ethyl acetate at 20℃; for 24h;	100%
With hydrogen; palladium 10% on activated carbon In ethyl acetate at 20℃; for 24h;	100%
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 2h;	98%

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

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

: 200002-41-1
(-)-[(1R,4S)-tert-butyl 3-oxo-2-azabicyclo(2.2.1)hept-5-ene-2-carboxylate]

Conditions

Conditions	Yield
With dmap; triethylamine In tetrahydrofuran	100%
With pyridine; dmap at 20℃; for 3h;	100%
With dmap; triethylamine In tetrahydrofuran at 0 - 20℃;	93%

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

: 71830-07-4
(1S,3R)-3-aminocyclopentanecarboxylic acid

Conditions

Conditions	Yield
With hydrogen; palladium 10% on activated carbon In ethyl acetate at 20℃; for 24h;	100%
With hydrogen; palladium 10% on activated carbon In ethyl acetate at 20℃; for 24h;	100%
Multi-step reaction with 3 steps 1: 79 percent / bromine / CH2Cl2 / 0.25 h / Ambient temperature 2: 87 percent / tributyltin hydride, azobisisobutyronitrile / toluene / 5 h / Heating 3: 97 percent / aq. HCl / Heating View Scheme

: 67-56-1
methanol

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

: (1R,4S)-methyl 4-aminocyclopent-2-enecarboxylate hydrochloride salt

Conditions

Conditions	Yield
With thionyl chloride at 0 - 20℃; for 12h;	100%

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

: (+)-methyl (1R,4S)-4-aminocyclopent-2-ene-1-carboxylate hydrochloride

Conditions

Conditions	Yield
With thionyl chloride; 2-azabicyclo[2.2.1.]hept-5-en-3-one In methanol at 20℃; for 2h;	100%
With thionyl chloride In methanol at 20℃; for 2h;	5.36 g

: 130931-83-8
(1S,4R)-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 10% on activated carbon In ethyl acetate at 20℃; for 24h;	100%

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

: (+/-)-cis-4-amino-2-cyclopentene-1-carboxylic acid methanesulfonate

Conditions

Conditions	Yield
	98.2%

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

: 262280-21-7
(1R,4R,6S,7R)-6,7-dibromo-2-azabicyclo[2.2.1]heptan-3-one

Conditions

Conditions	Yield
With bromine In dichloromethane at 0℃; for 2h; Bromination;	98%

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

: 625108-11-4
C7H13NO2

Conditions

Conditions	Yield
With hydrogen; palladium 10% on activated carbon In ethyl acetate at 20℃; for 24h;	96%
Stage #1: (1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one With hydrogen; palladium 10% on activated carbon In ethyl acetate at 20℃; for 24h; Stage #2: With hydrogenchloride In methanol; water at 20℃; for 72h;	96%
Multi-step reaction with 2 steps 1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 24 h / 20 °C 2: hydrogenchloride; water / 72 h / 20 °C View Scheme

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

: (1S,3R)-3-amino-cyclopentanecarboxylic acid methyl ester hydrochloride

Conditions

Conditions	Yield
Stage #1: (1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one With hydrogen; palladium 10% on activated carbon In ethyl acetate for 24h; Stage #2: With hydrogenchloride In methanol; water at 20℃; for 72h;	96%
Multi-step reaction with 2 steps 1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 24 h / 20 °C 2: hydrogenchloride / water / 72 h / 20 °C View Scheme

: 67-56-1
methanol

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

: (+)-methyl (1R,4S)-4-aminocyclopent-2-ene-1-carboxylate hydrochloride

Conditions

Conditions	Yield
With thionyl chloride at 2 - 8℃; for 1.5h; Inert atmosphere; Industrial scale;	95%
With thionyl chloride at 0℃; for 2h;
With thionyl chloride at 0 - 13℃; for 4.25h;
With hydrogenchloride In water for 16h; Sealed tube; Heating;

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

: 3355-28-0
1-Bromo-2-butyne

: 666256-77-5
(1S,4R)-2-But-2-ynyl-2-aza-bicyclo[2.2.1]hept-5-en-3-one

Conditions

Conditions	Yield
With potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate	92%

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

: 106-95-6
allyl bromide

: 406218-20-0
(1S)-2-(allyl)-2-azabicyclo[2.2.1]hept-5-en-3-one

Conditions

Conditions	Yield
With potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In acetonitrile for 3h; Heating;	90%

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

: 130931-85-0
(+)-(1R,4S)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In water for 2h; Reflux;	90%

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

: 74-88-4
methyl iodide

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

Conditions

Conditions	Yield
With caesium carbonate In butanone at 35℃; Inert atmosphere;	90%
Stage #1: (1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 0.5h; Stage #2: methyl iodide In tetrahydrofuran; mineral oil at 20℃; for 16h;	75%

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

: 824-94-2
p-methoxybenzyl chloride

: 169104-33-0
(1S,4R)-2-[(4-methoxyphenyl)methyl]-2-azabicyclo[2.2.1]hept-5-en-3-one

Conditions

Conditions	Yield
Stage #1: (1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Stage #2: p-methoxybenzyl chloride With tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃;	90%
Stage #1: (1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.0833333h; Stage #2: p-methoxybenzyl chloride With tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 4.5h;	21.4 g

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

: 824-94-2
p-methoxybenzyl chloride

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

Conditions

Conditions	Yield
Stage #1: (1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Stage #2: p-methoxybenzyl chloride With tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide; mineral oil at 0℃;	90%

: 64-17-5
ethanol

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

: 229613-87-0
(1R,4S)-ethyl 4-aminocyclopent-2-enecarboxylate hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride at 0℃; for 1h;	89%
With hydrogenchloride In water at 0℃; for 1h;	73%

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

: 99768-12-4
4-methoxycarbonylphenylboronic acid

: methyl 4-((1S,4S,6R)-3-oxo-2-azabicyclo[2.2.1]heptan-6-yl)benzoate

Conditions

Conditions	Yield
With [Rh(OH)(cod)]2; (2S)-1-[(1S)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene In tetrahydrofuran; water at 23℃; for 64h; Inert atmosphere; regioselective reaction;	89%

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

: (+)-cis-4-amino-2-cyclopentene-1-methanol

Conditions

Conditions	Yield
	88.8%

: 34619-03-9
tert-butyldicarbonate

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

: 168960-18-7
(1R,4S)-N-(tert-Butyloxycarbonyl)-1-amino-4-(hydroxymethyl)-2-cyclopentene

Conditions

Conditions	Yield
Stage #1: (1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one With methanesulfonic acid In tetrahydrofuran; water at 34 - 44℃; for 2.75h; Heating / reflux; Stage #2: With lithium aluminium tetrahydride In tetrahydrofuran for 18.5h; Heating / reflux; Stage #3: tert-butyldicarbonate With sodium fluoride more than 3 stages;	88%

: 16419-60-6
2-Methylphenylboronic acid

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

: (1S,4S,6R)-6-(o-tolyl)-2-azabicyclo[2.2.1]heptan-3-one

Conditions

Conditions	Yield
With [Rh(OH)(cod)]2; (2S)-1-[(1S)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene In tetrahydrofuran; water at 23℃; for 64h; Inert atmosphere; regioselective reaction;	87%

: 100-39-0
benzyl bromide

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

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

Conditions

Conditions	Yield
Stage #1: (1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 1h; Inert atmosphere; Stage #2: benzyl bromide In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil at 20℃; Inert atmosphere;	87%
Stage #1: (1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: benzyl bromide at 20℃; for 72h;

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

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

: 204913-00-8
(1R,4S)-tert-butyl 3-oxo-2-azabicyclo[2.2.1]heptane-2-carboxylate

Conditions

Conditions	Yield
Stage #1: (1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one With hydrogen; palladium 10% on activated carbon In methanol under 2585.81 Torr; for 1h; Stage #2: di-tert-butyl dicarbonate With dmap In dichloromethane at 20℃;	86%
Stage #1: (1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one With palladium 10% on activated carbon; hydrogen In methanol at 40℃; under 7500.75 Torr; Stage #2: di-tert-butyl dicarbonate With dmap In acetonitrile at 20℃; for 2h;	1.94 g

: 10365-98-7
3-methoxyphenylboronic acid

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

: (1S,4S,6R)-6-(3-methoxyphenyl)-2-azabicyclo[2.2.1]heptan-3-one

Conditions

Conditions	Yield
With [Rh(OH)(cod)]2; (2S)-1-[(1S)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene In tetrahydrofuran; water at 23℃; for 64h; Inert atmosphere; regioselective reaction;	86%

: 5162-44-7
1-bromo-4-butene

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

: 406218-21-1
(1S)-2-(but-3-enyl)-2-azabicyclo[2.2.1]hept-5-en-3-one

Conditions

Conditions	Yield
With potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In acetonitrile for 3h; Heating;	85%

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

: 106-96-7
propargyl bromide

: 666256-76-4
(1S,4R)-2-Prop-2-ynyl-2-aza-bicyclo[2.2.1]hept-5-en-3-one

Conditions

Conditions	Yield
With potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate	85%

: 128796-39-4
4-trifluoromethylphenylboronic acid

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

: (1S,4S,6R)-6-(4-(trifluoromethyl)phenyl)-2-azabicyclo[2.2.1]heptan-3-one

Conditions

Conditions	Yield
With [Rh(OH)(cod)]2; (2S)-1-[(1S)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene In tetrahydrofuran; water at 23℃; for 17h; Inert atmosphere; regioselective reaction;	83%

: 5467-74-3
4-Bromophenylboronic acid

: 130931-83-8
(1S,4R)-2-azabicyclo[2,2,1]hept-5-en-3-one

: (1S,4S,6R)-6-(4-bromophenyl)-2-azabicyclo[2.2.1]heptan-3-one

Conditions

Conditions	Yield
With [Rh(OH)(cod)]2; (2S)-1-[(1S)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene In tetrahydrofuran; water at 23℃; for 64h; Inert atmosphere; regioselective reaction;	83%

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

The (1S,4R)-2-Aza-bicyclo[2.2.1]hept-5-en-3-one, with the CAS registry number 130931-83-8, is also known as ZINC00158452. It belongs to the product categories of Chiral Building Blocks; Lactams; Organic Building Blocks. This chemical's molecular formula is C₆H₇NO and molecular weight is 109.12588. Its IUPAC name is called (1R,4S)-3-azabicyclo[2.2.1]hept-5-en-2-one. This chemical is off-white to beige crystalline powder. The product should be sealed and stored in cool and dry place.

Physical properties of (1S,4R)-2-Aza-bicyclo[2.2.1]hept-5-en-3-one: (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)Index of Refraction: 1.545; (11)Molar Refractivity: 28.8 cm³; (12)Molar Volume: 91 cm³; (13)Surface Tension: 39.4 dyne/cm; (14)Density: 1.198 g/cm³; (15)Flash Point: 167.1 °C; (16)Enthalpy of Vaporization: 56.09 kJ/mol; (17)Boiling Point: 319.3 °C at 760 mmHg; (18)Vapour Pressure: 0.000342 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
This chemical may cause inflammation to the skin or other mucous membranes. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. Whenever you will contact it, please wear suitable protective clothing.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1C2C=CC1NC2=O
(2)Isomeric SMILES: C1[C@@H]2C=C[C@H]1NC2=O
(3)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
(4)InChIKey: DDUFYKNOXPZZIW-CRCLSJGQSA-N

Product Name

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

Synthetic route

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

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