Product Name

  • Name

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

  • EINECS 418-530-1
  • CAS No. 79200-56-9
  • Article Data20
  • CAS DataBase
  • Density 1.198 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 crystals or crystalline powder
  • Safety 24-26-37/39
  • Risk Codes 22-41-43
  • Molecular Structure Molecular Structure of 79200-56-9 (((1R,4S)-2-Azabicyclo[2.2.1]hept-5-en-3-one)
  • Hazard Symbols HarmfulXn
  • Synonyms (1R,4S)-(-)-2-Azabicyclo[2.2.1]hept-5-en-3-one;
  • PSA 29.10000
  • LogP 0.38970

Synthetic route

(1R,4S)-N-hydroxymethyl-2-azabicyclo<2.2.1>hept-5-en-3-one
157810-21-4

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

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

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

Conditions
ConditionsYield
With methanol; ammonium hydroxide for 13h; Ambient temperature;51%
With ammonium hydroxide In methanol for 12h; Ambient temperature;51%
racemic 2-azabicyclo[2.2.1]hept-5-en-3-one
49805-30-3

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

A

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

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

B

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

(1R,4S)-4-aminocyclopenten-2-ene-1-carboxylic acid

Conditions
ConditionsYield
With (+)-γ-lactamase from Bradyrhizobium japonicum USDA 6 In aq. buffer at 45℃; for 1h; pH=8; Catalytic behavior; Temperature; pH-value; Resolution of racemate; Enzymatic reaction; enantioselective reaction;A 49.9%
B n/a
With cloned (+)-γ-lactamase at 25℃; for 1h; pH=7.5; Ring cleavage;
racemic 2-azabicyclo[2.2.1]hept-5-en-3-one
49805-30-3

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

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

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

Conditions
ConditionsYield
With A. viscous (NCIM No.2451) In phosphate buffer for 21h; pH=7.5;31.2%
With Penicillium thomi AM91 for 48h; Reagent/catalyst; Enzymatic reaction;n/a
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]hept-5-en-3-one
79200-56-9

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

(1R,4S)-2-(p-Methoxybenzyl)-2-azabicyclo<2.2.1>-5-hepten-3-one
168960-17-6

(1R,4S)-2-(p-Methoxybenzyl)-2-azabicyclo<2.2.1>-5-hepten-3-one

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

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

Conditions
ConditionsYield
With ammonium cerium(IV) nitrate In water; acetonitrile at 0℃; for 0.283333h; Yield given;
2-azabicyclo[2.2.1.]hept-5-en-3-one
49805-30-3

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

A

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

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

B

(1S,4R)-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
ConditionsYield
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;
2-azabicyclo[2.2.1.]hept-5-en-3-one
49805-30-3

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

A

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

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

B

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

(1R,4S)-4-aminocyclopenten-2-ene-1-carboxylic acid

Conditions
ConditionsYield
With lactamase Enzymatic reaction;
With Bradyrhizobium japonicum USDA 6 (+)-γ-lactamase In aq. buffer at 50℃; pH=6; Enzymatic reaction; enantioselective reaction;A n/a
B n/a
2-hydroxymethyl-2-azabicyclo<2.2.1>hept-5-en-3-one
157732-10-0

2-hydroxymethyl-2-azabicyclo<2.2.1>hept-5-en-3-one

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

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 43 percent / various solvent(s) / 0.5 h / Ambient temperature; immobilized lipase PS on diatomite
2: 90 percent / H2O / diisopropyl ether / 3 h / Ambient temperature; lipase PS
3: 51 percent / aq. NH3 / methanol / 12 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
2: 51 percent / Nh4OH, MeOH / 13 h / Ambient temperature
View Scheme
N-acetoxymethyl-2-azabicyclo[2.2.1]hept-5-en-3-one
183074-62-6

N-acetoxymethyl-2-azabicyclo[2.2.1]hept-5-en-3-one

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

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 41 percent / H2O / diisopropyl ether / 3 h / Ambient temperature; lipase PS
2: 51 percent / aq. NH3 / methanol / 12 h / Ambient temperature
View Scheme
(1R,4S)-N-acetoxymethyl-2-azabicyclo[2.2.1]hept-5-en-3-one
157732-11-1

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

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

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 90 percent / H2O / diisopropyl ether / 3 h / Ambient temperature; lipase PS
2: 51 percent / aq. NH3 / methanol / 12 h / Ambient temperature
View Scheme
(1R,4S,6S)-6-(tert-Butyldimethylsiloxy)-2-azabicyclo<2.2.1>-3-heptanone
168773-48-6

(1R,4S,6S)-6-(tert-Butyldimethylsiloxy)-2-azabicyclo<2.2.1>-3-heptanone

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

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

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h
2: 97 percent / TBAF / tetrahydrofuran / 0.33 h
3: 97 percent / PPh3, imidazole, I2 / toluene / 1.) 60 deg C, 10 min, 2.) reflux, 3.75 h
4: 98 percent / DBU / xylene / 16.5 h / Heating
5: CAN / acetonitrile; H2O / 0.28 h / 0 °C
View Scheme
Multi-step reaction with 6 steps
1: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h
2: 97 percent / TBAF / tetrahydrofuran / 0.33 h
3: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min
4: 20 percent
5: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h
6: CAN / acetonitrile; H2O / 0.28 h / 0 °C
View Scheme
Multi-step reaction with 6 steps
1: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h
2: 97 percent / TBAF / tetrahydrofuran / 0.33 h
3: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min
4: 40 percent / LiHMDS
5: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h
6: CAN / acetonitrile; H2O / 0.28 h / 0 °C
View Scheme
(1R,4S,6R)-6-Iodo-2-(p-methoxybenzyl)-2-azabicyclo<2.2.1>-3-heptanone
168773-56-6

(1R,4S,6R)-6-Iodo-2-(p-methoxybenzyl)-2-azabicyclo<2.2.1>-3-heptanone

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

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 98 percent / DBU / xylene / 16.5 h / Heating
2: CAN / acetonitrile; H2O / 0.28 h / 0 °C
View Scheme
(1R,4S,6S)-6-Hydroxy-2-(p-methoxybenzyl)-2-azabicyclo<2.2.1>-3-heptanone
168773-55-5

(1R,4S,6S)-6-Hydroxy-2-(p-methoxybenzyl)-2-azabicyclo<2.2.1>-3-heptanone

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

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 97 percent / PPh3, imidazole, I2 / toluene / 1.) 60 deg C, 10 min, 2.) reflux, 3.75 h
2: 98 percent / DBU / xylene / 16.5 h / Heating
3: CAN / acetonitrile; H2O / 0.28 h / 0 °C
View Scheme
Multi-step reaction with 4 steps
1: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min
2: 20 percent
3: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h
4: CAN / acetonitrile; H2O / 0.28 h / 0 °C
View Scheme
Multi-step reaction with 4 steps
1: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min
2: 40 percent / LiHMDS
3: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h
4: CAN / acetonitrile; H2O / 0.28 h / 0 °C
View Scheme
(1R,4S)-2-(p-Methoxybenzyl)-2-azabicylo<2.2.1>heptane-3,6-dione
168773-57-7

(1R,4S)-2-(p-Methoxybenzyl)-2-azabicylo<2.2.1>heptane-3,6-dione

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

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

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 20 percent
2: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h
3: CAN / acetonitrile; H2O / 0.28 h / 0 °C
View Scheme
Multi-step reaction with 3 steps
1: 40 percent / LiHMDS
2: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h
3: CAN / acetonitrile; H2O / 0.28 h / 0 °C
View Scheme
(1R,4S,6S)-6-(tert-Butyldimethylsiloxy)-2-benzyl-2-azabicyclo<2.2.1>-3-heptanone
168773-42-0

(1R,4S,6S)-6-(tert-Butyldimethylsiloxy)-2-benzyl-2-azabicyclo<2.2.1>-3-heptanone

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

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

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min
2: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h
3: 97 percent / TBAF / tetrahydrofuran / 0.33 h
4: 97 percent / PPh3, imidazole, I2 / toluene / 1.) 60 deg C, 10 min, 2.) reflux, 3.75 h
5: 98 percent / DBU / xylene / 16.5 h / Heating
6: CAN / acetonitrile; H2O / 0.28 h / 0 °C
View Scheme
Multi-step reaction with 7 steps
1: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min
2: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h
3: 97 percent / TBAF / tetrahydrofuran / 0.33 h
4: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min
5: 20 percent
6: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h
7: CAN / acetonitrile; H2O / 0.28 h / 0 °C
View Scheme
Multi-step reaction with 7 steps
1: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min
2: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h
3: 97 percent / TBAF / tetrahydrofuran / 0.33 h
4: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min
5: 40 percent / LiHMDS
6: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h
7: CAN / acetonitrile; H2O / 0.28 h / 0 °C
View Scheme
(5S,6R)-1-Benzyl-5-<(tert-butyldimethylsilyl)oxy>-6-(bromomethyl)-2-piperidinone
168773-45-3

(5S,6R)-1-Benzyl-5-<(tert-butyldimethylsilyl)oxy>-6-(bromomethyl)-2-piperidinone

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

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

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min
2: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min
3: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h
4: 97 percent / TBAF / tetrahydrofuran / 0.33 h
5: 97 percent / PPh3, imidazole, I2 / toluene / 1.) 60 deg C, 10 min, 2.) reflux, 3.75 h
6: 98 percent / DBU / xylene / 16.5 h / Heating
7: CAN / acetonitrile; H2O / 0.28 h / 0 °C
View Scheme
Multi-step reaction with 8 steps
1: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min
2: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min
3: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h
4: 97 percent / TBAF / tetrahydrofuran / 0.33 h
5: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min
6: 20 percent
7: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h
8: CAN / acetonitrile; H2O / 0.28 h / 0 °C
View Scheme
Multi-step reaction with 8 steps
1: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min
2: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min
3: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h
4: 97 percent / TBAF / tetrahydrofuran / 0.33 h
5: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min
6: 40 percent / LiHMDS
7: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h
8: CAN / acetonitrile; H2O / 0.28 h / 0 °C
View Scheme
(5S,6R)-1-Benzyl-5-<(tert-butyldimethylsilyl)oxy>-6-(hydroxymethyl)-2-piperidinone
168773-41-9

(5S,6R)-1-Benzyl-5-<(tert-butyldimethylsilyl)oxy>-6-(hydroxymethyl)-2-piperidinone

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

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

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 93 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 13 h
2: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min
3: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min
4: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h
5: 97 percent / TBAF / tetrahydrofuran / 0.33 h
6: 97 percent / PPh3, imidazole, I2 / toluene / 1.) 60 deg C, 10 min, 2.) reflux, 3.75 h
7: 98 percent / DBU / xylene / 16.5 h / Heating
8: CAN / acetonitrile; H2O / 0.28 h / 0 °C
View Scheme
Multi-step reaction with 9 steps
1: 93 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 13 h
2: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min
3: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min
4: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h
5: 97 percent / TBAF / tetrahydrofuran / 0.33 h
6: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min
7: 20 percent
8: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h
9: CAN / acetonitrile; H2O / 0.28 h / 0 °C
View Scheme
Multi-step reaction with 9 steps
1: 93 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 13 h
2: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min
3: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min
4: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h
5: 97 percent / TBAF / tetrahydrofuran / 0.33 h
6: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min
7: 40 percent / LiHMDS
8: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h
9: CAN / acetonitrile; H2O / 0.28 h / 0 °C
View Scheme
(1R,4S,6S)-6-(tert-Butyldimethylsiloxy)-2-(p-methoxybenzyl)-2-azabicyclo<2.2.1>-3-heptanone
168773-47-5

(1R,4S,6S)-6-(tert-Butyldimethylsiloxy)-2-(p-methoxybenzyl)-2-azabicyclo<2.2.1>-3-heptanone

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

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

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 97 percent / TBAF / tetrahydrofuran / 0.33 h
2: 97 percent / PPh3, imidazole, I2 / toluene / 1.) 60 deg C, 10 min, 2.) reflux, 3.75 h
3: 98 percent / DBU / xylene / 16.5 h / Heating
4: CAN / acetonitrile; H2O / 0.28 h / 0 °C
View Scheme
Multi-step reaction with 5 steps
1: 97 percent / TBAF / tetrahydrofuran / 0.33 h
2: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min
3: 20 percent
4: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h
5: CAN / acetonitrile; H2O / 0.28 h / 0 °C
View Scheme
Multi-step reaction with 5 steps
1: 97 percent / TBAF / tetrahydrofuran / 0.33 h
2: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min
3: 40 percent / LiHMDS
4: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h
5: CAN / acetonitrile; H2O / 0.28 h / 0 °C
View Scheme
(5S,6R)-1-(p-Methoxybenzyl)-5-<(tert-butyldimethylsilyl)oxy>-6-(hydroxymethyl)-2-piperidinone
168773-44-2

(5S,6R)-1-(p-Methoxybenzyl)-5-<(tert-butyldimethylsilyl)oxy>-6-(hydroxymethyl)-2-piperidinone

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

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

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 89 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 22 h
2: 90 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min
3: 97 percent / TBAF / tetrahydrofuran / 0.33 h
4: 97 percent / PPh3, imidazole, I2 / toluene / 1.) 60 deg C, 10 min, 2.) reflux, 3.75 h
5: 98 percent / DBU / xylene / 16.5 h / Heating
6: CAN / acetonitrile; H2O / 0.28 h / 0 °C
View Scheme
Multi-step reaction with 7 steps
1: 89 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 22 h
2: 90 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min
3: 97 percent / TBAF / tetrahydrofuran / 0.33 h
4: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min
5: 20 percent
6: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h
7: CAN / acetonitrile; H2O / 0.28 h / 0 °C
View Scheme
Multi-step reaction with 7 steps
1: 89 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 22 h
2: 90 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min
3: 97 percent / TBAF / tetrahydrofuran / 0.33 h
4: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min
5: 40 percent / LiHMDS
6: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h
7: CAN / acetonitrile; H2O / 0.28 h / 0 °C
View Scheme
(5S,6R)-1-(p-Methoxybenzyl)-5-<(tert-butyldimethylsilyl)oxy>-6-(bromomethyl)-2-piperidinone
168773-46-4

(5S,6R)-1-(p-Methoxybenzyl)-5-<(tert-butyldimethylsilyl)oxy>-6-(bromomethyl)-2-piperidinone

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

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

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 90 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min
2: 97 percent / TBAF / tetrahydrofuran / 0.33 h
3: 97 percent / PPh3, imidazole, I2 / toluene / 1.) 60 deg C, 10 min, 2.) reflux, 3.75 h
4: 98 percent / DBU / xylene / 16.5 h / Heating
5: CAN / acetonitrile; H2O / 0.28 h / 0 °C
View Scheme
Multi-step reaction with 6 steps
1: 90 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min
2: 97 percent / TBAF / tetrahydrofuran / 0.33 h
3: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min
4: 20 percent
5: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h
6: CAN / acetonitrile; H2O / 0.28 h / 0 °C
View Scheme
Multi-step reaction with 6 steps
1: 90 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min
2: 97 percent / TBAF / tetrahydrofuran / 0.33 h
3: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min
4: 40 percent / LiHMDS
5: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h
6: CAN / acetonitrile; H2O / 0.28 h / 0 °C
View Scheme
(5S,6R)-1-Benzyl-5-<(tert-butyldimethylsilyl)oxy>-6-<(benzyloxy)methyl>-2-piperidinone
168773-40-8

(5S,6R)-1-Benzyl-5-<(tert-butyldimethylsilyl)oxy>-6-<(benzyloxy)methyl>-2-piperidinone

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

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

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: 100 percent / H2 / 10percent Pd/C / ethanol / 23 h
2: 93 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 13 h
3: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min
4: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min
5: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h
6: 97 percent / TBAF / tetrahydrofuran / 0.33 h
7: 97 percent / PPh3, imidazole, I2 / toluene / 1.) 60 deg C, 10 min, 2.) reflux, 3.75 h
8: 98 percent / DBU / xylene / 16.5 h / Heating
9: CAN / acetonitrile; H2O / 0.28 h / 0 °C
View Scheme
Multi-step reaction with 10 steps
1: 100 percent / H2 / 10percent Pd/C / ethanol / 23 h
2: 93 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 13 h
3: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min
4: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min
5: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h
6: 97 percent / TBAF / tetrahydrofuran / 0.33 h
7: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min
8: 20 percent
9: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h
10: CAN / acetonitrile; H2O / 0.28 h / 0 °C
View Scheme
Multi-step reaction with 10 steps
1: 100 percent / H2 / 10percent Pd/C / ethanol / 23 h
2: 93 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 13 h
3: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min
4: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min
5: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h
6: 97 percent / TBAF / tetrahydrofuran / 0.33 h
7: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min
8: 40 percent / LiHMDS
9: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h
10: CAN / acetonitrile; H2O / 0.28 h / 0 °C
View Scheme
Trifluoro-methanesulfonic acid (1R,4S)-2-(4-methoxy-benzyl)-3-oxo-2-aza-bicyclo[2.2.1]hept-5-en-6-yl ester
168773-58-8

Trifluoro-methanesulfonic acid (1R,4S)-2-(4-methoxy-benzyl)-3-oxo-2-aza-bicyclo[2.2.1]hept-5-en-6-yl ester

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

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h
2: CAN / acetonitrile; H2O / 0.28 h / 0 °C
View Scheme
(5S,6R)-1-(p-Methoxybenzyl)-5-<(tert-butyldimethylsilyl)oxy>-6-<(benzyloxy)methyl>-2-piperidinone
168773-43-1

(5S,6R)-1-(p-Methoxybenzyl)-5-<(tert-butyldimethylsilyl)oxy>-6-<(benzyloxy)methyl>-2-piperidinone

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

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

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 100 percent / H2 / 10percent Pd/C / ethanol / 23 h
2: 89 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 22 h
3: 90 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min
4: 97 percent / TBAF / tetrahydrofuran / 0.33 h
5: 97 percent / PPh3, imidazole, I2 / toluene / 1.) 60 deg C, 10 min, 2.) reflux, 3.75 h
6: 98 percent / DBU / xylene / 16.5 h / Heating
7: CAN / acetonitrile; H2O / 0.28 h / 0 °C
View Scheme
Multi-step reaction with 8 steps
1: 100 percent / H2 / 10percent Pd/C / ethanol / 23 h
2: 89 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 22 h
3: 90 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min
4: 97 percent / TBAF / tetrahydrofuran / 0.33 h
5: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min
6: 20 percent
7: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h
8: CAN / acetonitrile; H2O / 0.28 h / 0 °C
View Scheme
Multi-step reaction with 8 steps
1: 100 percent / H2 / 10percent Pd/C / ethanol / 23 h
2: 89 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 22 h
3: 90 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min
4: 97 percent / TBAF / tetrahydrofuran / 0.33 h
5: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min
6: 40 percent / LiHMDS
7: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h
8: CAN / acetonitrile; H2O / 0.28 h / 0 °C
View Scheme
(6R)-5-Hydroxy-6-<(benzyloxy)methyl>-2-piperidinone

(6R)-5-Hydroxy-6-<(benzyloxy)methyl>-2-piperidinone

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

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

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: imidazole / dimethylformamide / 15 h
2: 99 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 42 h
3: 100 percent / H2 / 10percent Pd/C / ethanol / 23 h
4: 93 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 13 h
5: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min
6: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min
7: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h
8: 97 percent / TBAF / tetrahydrofuran / 0.33 h
9: 97 percent / PPh3, imidazole, I2 / toluene / 1.) 60 deg C, 10 min, 2.) reflux, 3.75 h
10: 98 percent / DBU / xylene / 16.5 h / Heating
11: CAN / acetonitrile; H2O / 0.28 h / 0 °C
View Scheme
Multi-step reaction with 12 steps
1: imidazole / dimethylformamide / 15 h
2: 99 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 42 h
3: 100 percent / H2 / 10percent Pd/C / ethanol / 23 h
4: 93 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 13 h
5: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min
6: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min
7: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h
8: 97 percent / TBAF / tetrahydrofuran / 0.33 h
9: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min
10: 20 percent
11: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h
12: CAN / acetonitrile; H2O / 0.28 h / 0 °C
View Scheme
Multi-step reaction with 12 steps
1: imidazole / dimethylformamide / 15 h
2: 99 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 42 h
3: 100 percent / H2 / 10percent Pd/C / ethanol / 23 h
4: 93 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 13 h
5: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min
6: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min
7: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h
8: 97 percent / TBAF / tetrahydrofuran / 0.33 h
9: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min
10: 40 percent / LiHMDS
11: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h
12: CAN / acetonitrile; H2O / 0.28 h / 0 °C
View Scheme
(5S,6R)-5-Hydroxy-6-<(benzyloxy)methyl>-2-piperidinone
168773-36-2

(5S,6R)-5-Hydroxy-6-<(benzyloxy)methyl>-2-piperidinone

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

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

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1: 92 percent / imidazole / dimethylformamide / 15 h
2: 99 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 42 h
3: 100 percent / H2 / 10percent Pd/C / ethanol / 23 h
4: 93 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 13 h
5: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min
6: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min
7: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h
8: 97 percent / TBAF / tetrahydrofuran / 0.33 h
9: 97 percent / PPh3, imidazole, I2 / toluene / 1.) 60 deg C, 10 min, 2.) reflux, 3.75 h
10: 98 percent / DBU / xylene / 16.5 h / Heating
11: CAN / acetonitrile; H2O / 0.28 h / 0 °C
View Scheme
Multi-step reaction with 12 steps
1: 92 percent / imidazole / dimethylformamide / 15 h
2: 99 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 42 h
3: 100 percent / H2 / 10percent Pd/C / ethanol / 23 h
4: 93 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 13 h
5: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min
6: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min
7: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h
8: 97 percent / TBAF / tetrahydrofuran / 0.33 h
9: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min
10: 20 percent
11: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h
12: CAN / acetonitrile; H2O / 0.28 h / 0 °C
View Scheme
Multi-step reaction with 12 steps
1: 92 percent / imidazole / dimethylformamide / 15 h
2: 99 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 42 h
3: 100 percent / H2 / 10percent Pd/C / ethanol / 23 h
4: 93 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 13 h
5: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min
6: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min
7: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h
8: 97 percent / TBAF / tetrahydrofuran / 0.33 h
9: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min
10: 40 percent / LiHMDS
11: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h
12: CAN / acetonitrile; H2O / 0.28 h / 0 °C
View Scheme
(5S,6R)-5-<(tert-Butyldimethylsilyl)oxy>-6-<(benzyloxy)methyl>-2-piperidinone
168773-38-4

(5S,6R)-5-<(tert-Butyldimethylsilyl)oxy>-6-<(benzyloxy)methyl>-2-piperidinone

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

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

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 99 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 42 h
2: 100 percent / H2 / 10percent Pd/C / ethanol / 23 h
3: 93 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 13 h
4: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min
5: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min
6: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h
7: 97 percent / TBAF / tetrahydrofuran / 0.33 h
8: 97 percent / PPh3, imidazole, I2 / toluene / 1.) 60 deg C, 10 min, 2.) reflux, 3.75 h
9: 98 percent / DBU / xylene / 16.5 h / Heating
10: CAN / acetonitrile; H2O / 0.28 h / 0 °C
View Scheme
Multi-step reaction with 11 steps
1: 99 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 42 h
2: 100 percent / H2 / 10percent Pd/C / ethanol / 23 h
3: 93 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 13 h
4: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min
5: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min
6: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h
7: 97 percent / TBAF / tetrahydrofuran / 0.33 h
8: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min
9: 20 percent
10: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h
11: CAN / acetonitrile; H2O / 0.28 h / 0 °C
View Scheme
Multi-step reaction with 11 steps
1: 99 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 42 h
2: 100 percent / H2 / 10percent Pd/C / ethanol / 23 h
3: 93 percent / CBr4, PPh3 / CH2Cl2 / 1.) 0 deg C to r.t., 1 h, 2.) r.t., 13 h
4: 99 percent / KHMDS / tetrahydrofuran / 1.) -50 to -35 deg C, 15 min, 2.) -35 deg C, 40 min
5: 99 percent / NH3, Na, t-BuOH / tetrahydrofuran / 1.) -78 deg C, 6 min, 2.) -78 to -33 deg C, 2 min
6: 90 percent / NaH, TBAI / tetrahydrofuran / 1.) 15 min, 2.) 21 h
7: 97 percent / TBAF / tetrahydrofuran / 0.33 h
8: 1.) (COCl)2, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) -78 deg C to r.t., 20 min; r.t., 40 min
9: 40 percent / LiHMDS
10: 39 percent / HCO2H, Bu3N / PPh3, Pd(OAc)2 / dimethylformamide / 6 h
11: CAN / acetonitrile; H2O / 0.28 h / 0 °C
View Scheme
(–)-methyl (1S,4R)-4-aminocyclopent-2-ene-1-carboxylate hydrochloride
229613-83-6

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

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

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

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

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

A

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

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

B

(1S,4R)-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

C

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

(1R,4S)-4-aminocyclopenten-2-ene-1-carboxylic acid

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

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

A

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

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

B

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

(1R,4S)-4-aminocyclopenten-2-ene-1-carboxylic acid

C

(-)-(1S, 4R)-4-amino-2-cyclopentene-1-carboxylic acid
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
ConditionsYield
With Rhodococcus globerulus-amidase (AMI) 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 2-azabicyclo[2.2.1]hept-5-en-3-one
49805-30-3

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

A

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

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

B

(1S,4R)-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

C

(-)-(1S, 4R)-4-amino-2-cyclopentene-1-carboxylic acid
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
ConditionsYield
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
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

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

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

tert-butyl (1R,4S)-(-)-3-oxo-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate
151792-53-9

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

Conditions
ConditionsYield
With dmap; triethylamine In tetrahydrofuran100%
With dmap In tetrahydrofuran at 20℃; for 3h;99%
With dmap In dichloromethane for 16h; Inert atmosphere;98%
methanol
67-56-1

methanol

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

(-)-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 thionyl chloride at 0℃; for 2h;100%
With thionyl chloride at 0 - 20℃; for 14h;100%
With thionyl chloride at 0℃;100%
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
79200-56-9

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

(+)-2-Azabicyclo<2.2.1>heptan-3-one
134003-03-5

(+)-2-Azabicyclo<2.2.1>heptan-3-one

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In methanol at 20℃; for 5h; atmospheric pressure;100%
With hydrogen; acetic acid; palladium on activated charcoal In ethyl acetate at 20℃; under 2068.59 Torr; for 1.5h;98%
With palladium 10% on activated carbon; hydrogen In methanol for 3h;98%
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
79200-56-9

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

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

(1S,3R)-3-aminocyclopentanecarboxylic acid

Conditions
ConditionsYield
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%
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
79200-56-9

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

(1S,4R)-(-)ethyl-4-aminocyclopent-2-ene-1-carboxylate hydrochloride
229613-86-9

(1S,4R)-(-)ethyl-4-aminocyclopent-2-ene-1-carboxylate hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In ethanol for 2h; Heating / reflux;100%
With thionyl chloride In ethanol at 10 - 30℃; for 1h; Solvent; Reagent/catalyst;
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
79200-56-9

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

(1R,4S,5R,6S)-5,6-dihydroxy-2-azabicyclo[2.2.1]heptan-3-one
79200-55-8

(1R,4S,5R,6S)-5,6-dihydroxy-2-azabicyclo[2.2.1]heptan-3-one

Conditions
ConditionsYield
With osmium(VIII) oxide; 4-methylmorpholine N-oxide In 1,4-dioxane at 0 - 20℃; for 3h;98%
With osmium(VIII) oxide; 4-methylmorpholine N-oxide; 4-methylmorpholine 4-oxide monohydrate In 1,4-dioxane; water at 0 - 20℃; for 3h;98%
With osmium(VIII) oxide; 4-methylmorpholine N-oxide In water; tert-butyl alcohol at 70℃; for 0.5h;94%
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
79200-56-9

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

toluene-4-sulfonic acid
104-15-4

toluene-4-sulfonic acid

(1S,cis)-4-amino-2-cyclopentene-1-carboxylic acid 4-toluenesulfonate

(1S,cis)-4-amino-2-cyclopentene-1-carboxylic acid 4-toluenesulfonate

Conditions
ConditionsYield
In tetrahydrofuran; water at 20 - 60℃; for 18h; Ring cleavage;97%
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
79200-56-9

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

(-)-(1S,4R)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride
130931-84-9

(-)-(1S,4R)-4-aminocyclopent-2-ene-1-carboxylic acid hydrochloride

Conditions
ConditionsYield
With hydrogenchloride95%
With hydrogenchloride for 1h; Heating;
With hydrogenchloride; water at 80℃; for 2h;
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
79200-56-9

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

acryloyl chloride
814-68-6

acryloyl chloride

C9H9NO2

C9H9NO2

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃; Inert atmosphere;95%
pent-4-enoyl chloride
39716-58-0

pent-4-enoyl chloride

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

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

C11H13NO2

C11H13NO2

Conditions
ConditionsYield
Stage #1: (-)-2-azabicyclo[2.2.1]hept-5-en-3-one With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere;
Stage #2: pent-4-enoyl chloride In tetrahydrofuran at 20℃; Inert atmosphere;		91%
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
79200-56-9

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

benzoyl chloride
98-88-4

benzoyl chloride

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

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

Conditions
ConditionsYield
In pyridine90%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

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

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

tert-butyl (1R,4S)-(+)-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate
702666-73-7

tert-butyl (1R,4S)-(+)-2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate

Conditions
ConditionsYield
Stage #1: (-)-2-azabicyclo[2.2.1]hept-5-en-3-one With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether for 7h; Heating;
Stage #2: di-tert-butyl dicarbonate at 25℃; for 14h; Further stages.;		87%
Stage #1: (-)-2-azabicyclo[2.2.1]hept-5-en-3-one With lithium aluminium tetrahydride In tetrahydrofuran; diethyl ether for 7h; Heating;
Stage #2: di-tert-butyl dicarbonate at 20℃; for 14h; Further stages.;		52%
methanol
67-56-1

methanol

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

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

(1R,3S)-methyl 3-aminocyclopentanecarboxylate hydrochloride

(1R,3S)-methyl 3-aminocyclopentanecarboxylate hydrochloride

Conditions
ConditionsYield
Stage #1: (-)-2-azabicyclo[2.2.1]hept-5-en-3-one With palladium 10% on activated carbon; hydrogen In ethyl acetate at 20℃; for 12h;
Stage #2: methanol With thionyl chloride at 0 - 20℃; for 24h;		84%
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
79200-56-9

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

p-methoxybenzyl chloride
824-94-2

p-methoxybenzyl chloride

(1R,4S)-2-(p-Methoxybenzyl)-2-azabicyclo<2.2.1>-5-hepten-3-one
168960-17-6

(1R,4S)-2-(p-Methoxybenzyl)-2-azabicyclo<2.2.1>-5-hepten-3-one

Conditions
ConditionsYield
With tetra-(n-butyl)ammonium iodide; sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 2h;83%
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 50℃; for 3h; Inert atmosphere;75%
Stage #1: (-)-2-azabicyclo[2.2.1]hept-5-en-3-one With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide for 0.5h; Cooling with ice;
Stage #2: p-methoxybenzyl chloride With tetra-(n-butyl)ammonium iodide In tetrahydrofuran; N,N-dimethyl-formamide at 0 - 20℃; for 3h;		65%
With potassium hydroxide Yield given;
Stage #1: (-)-2-azabicyclo[2.2.1]hept-5-en-3-one With tetra-(n-butyl)ammonium iodide; sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 0℃; for 0.5h;
Stage #2: p-methoxybenzyl chloride In tetrahydrofuran; N,N-dimethyl-formamide at 0 - 25℃; for 1h; Solvent; Reagent/catalyst; Temperature;
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
79200-56-9

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

4-iodo-2-methoxybenzoic acid-methyl ester
148490-97-5

4-iodo-2-methoxybenzoic acid-methyl ester

methyl 2-methoxy-4-((1R,4S)-3-oxo-2-azabicyclo[2.2.1]hept-5-en-2-yl)benzoate
1311258-54-4

methyl 2-methoxy-4-((1R,4S)-3-oxo-2-azabicyclo[2.2.1]hept-5-en-2-yl)benzoate

Conditions
ConditionsYield
With potassium phosphate; copper(l) iodide; N,N`-dimethylethylenediamine In toluene at 110℃; for 18h; Inert atmosphere;74%
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
79200-56-9

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

4-Methoxybenzyl alcohol
105-13-5

4-Methoxybenzyl alcohol

(1R,4S)-2-(p-Methoxybenzyl)-2-azabicyclo<2.2.1>-5-hepten-3-one
168960-17-6

(1R,4S)-2-(p-Methoxybenzyl)-2-azabicyclo<2.2.1>-5-hepten-3-one

Conditions
ConditionsYield
Stage #1: 4-Methoxybenzyl alcohol With hydrogenchloride In water for 1h;
Stage #2: (-)-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 6.5h; Inert atmosphere;		73%
ethene
74-85-1

ethene

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

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

(3S,5R)-(-)-3,5-divinylpyrrolidin-2-one

(3S,5R)-(-)-3,5-divinylpyrrolidin-2-one

Conditions
ConditionsYield
tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 20℃; under 760.051 Torr; for 2.5h;70%
oxirane
75-21-8

oxirane

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

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

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

(1R,4S)-2-(2-hydroxyethyl)-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 lithium diisopropyl amide In tetrahydrofuran for 1h;
Stage #2: oxirane In tetrahydrofuran		67%
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
79200-56-9

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

benzyl chloroformate
501-53-1

benzyl chloroformate

(1R,45)-benzyl 2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate

(1R,45)-benzyl 2-azabicyclo[2.2.1]hept-5-ene-2-carboxylate

Conditions
ConditionsYield
Stage #1: (-)-2-azabicyclo[2.2.1]hept-5-en-3-one With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 60℃; for 27h; Inert atmosphere;
Stage #2: benzyl chloroformate With trimethylamine In tetrahydrofuran; water at 0 - 20℃; for 48h;		63%
but-3-enoyl chloride
1470-91-3

but-3-enoyl chloride

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

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

C10H11NO2

C10H11NO2

Conditions
ConditionsYield
Stage #1: (-)-2-azabicyclo[2.2.1]hept-5-en-3-one With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere;
Stage #2: but-3-enoyl chloride In tetrahydrofuran at 20℃; Inert atmosphere;		63%
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
79200-56-9

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

benzenesulfonyl chloride
98-09-9

benzenesulfonyl chloride

(1R)-2-aza-2-(benzenesulfonyl)bicyclo[2.2.1]hept-5-ene-3-one

(1R)-2-aza-2-(benzenesulfonyl)bicyclo[2.2.1]hept-5-ene-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 - 20℃; Inert atmosphere;
Stage #2: benzenesulfonyl chloride In tetrahydrofuran; mineral oil at 20℃; for 1.5h; Inert atmosphere;		62%
diazomethane
186581-53-3, 908094-01-9

diazomethane

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

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

(-)-exo-7-azatricyclo[3.2.1.02.4]octan-6-one

(-)-exo-7-azatricyclo[3.2.1.02.4]octan-6-one

Conditions
ConditionsYield
palladium diacetate In diethyl ether at 20℃; for 24h;62%
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
79200-56-9

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

isoprene
78-79-5

isoprene

2-(3-methylbut-2-enyl)-2-azabicyclo[2.2.1]hept-5-en-3-one

2-(3-methylbut-2-enyl)-2-azabicyclo[2.2.1]hept-5-en-3-one

Conditions
ConditionsYield
With bis[chloro(1,2,3-trihapto-allylbenzene)palladium(II)]; 1,3-bis-(diphenylphosphino)propane; sodium carbonate In toluene at 140℃; for 20h; Inert atmosphere; regioselective reaction;55%
2-(chloromethyl)iodobenzene
59473-45-9

2-(chloromethyl)iodobenzene

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

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

N-(2'-iodobenzyl)-2-aza-3-oxobicyclo[2.2.1]hept-5-ene
195830-50-3

N-(2'-iodobenzyl)-2-aza-3-oxobicyclo[2.2.1]hept-5-ene

Conditions
ConditionsYield
Stage #1: (-)-2-azabicyclo[2.2.1]hept-5-en-3-one With sodium hydride In tetrahydrofuran at 20℃; for 1h; Metallation;
Stage #2: 2-(chloromethyl)iodobenzene In tetrahydrofuran for 12h; Alkylation; Heating;		53%
With sodium hydride In tetrahydrofuran at 65℃; for 16h; Substitution;53%
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
79200-56-9

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

(1S,2R,4S,5R)-3-oxa-6-azatricyclo[3.2.1.02,4]octan-7-one
329910-40-9

(1S,2R,4S,5R)-3-oxa-6-azatricyclo[3.2.1.02,4]octan-7-one

Conditions
ConditionsYield
With disodium hydrogenphosphate; sodium dihydrogenphosphate In water at 0℃; for 7h; pH=6;26.16%
(-)-2-azabicyclo[2.2.1]hept-5-en-3-one
79200-56-9

(-)-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 acetone Inert atmosphere;25%
acetic anhydride
108-24-7

acetic anhydride

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

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

(-)-(1S,4R)-4-acetamidocyclopent-2-enylmethanol
130931-86-1

(-)-(1S,4R)-4-acetamidocyclopent-2-enylmethanol

Conditions
ConditionsYield
Yield given. Multistep reaction;

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

The 2-Azabicyclo[2.2.1]hept-5-en-3-one,(1R,4S)-, with the CAS registry number 79200-56-9, is also known as (-)-Vince lactam. It belongs to the product categories of Antiviral Agents; Chiral Building Blocks; Lactams; Organic Building Blocks; Chiral Reagents; Heterocycles; Intermediates. Its EINECS registry number is 418-530-1. This chemical's molecular formula is C6H7NO and molecular weight is 109.13. What's more, both its IUPAC name and systematic name are the same which is called (1R,4S)-2-Azabicyclo[2.2.1]hept-5-en-3-one. It should be stored in a cool, dry and well-ventilated place.

Physical properties about 2-Azabicyclo[2.2.1]hept-5-en-3-one,(1R,4S)- are: (1)ACD/LogP: -0.065; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.07; (4)ACD/LogD (pH 7.4): -0.07; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 21.97; (8)ACD/KOC (pH 7.4): 21.97; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 29.1 Å2; (13)Index of Refraction: 1.546; (14)Molar Refractivity: 28.805 cm3; (15)Molar Volume: 91.037 cm3; (16)Polarizability: 11.419×10-24cm3; (17)Surface Tension: 39.449 dyne/cm; (18)Density: 1.199 g/cm3; (19)Flash Point: 167.131 °C; (20)Enthalpy of Vaporization: 56.087 kJ/mol; (21)Boiling Point: 319.302 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25 °C.

When you are dealing with this chemical, you should be very careful. This chemical may cause damage to health. It is harmful if swallowed and has serious damage to eyes. It may cause sensitisation by skin contact. Therefore, you should wear suitable gloves, eye/face protection and avoid contacting with skin. In case of contacting with eyes, you should rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C1N[C@H]2\C=C/[C@@H]1C2
(2) InChI: InChI=1S/C6H7NO/c8-6-4-1-2-5(3-4)7-6/h1-2,4-5H,3H2,(H,7,8)/t4-,5+/m1/s1
(3) InChIKey: DDUFYKNOXPZZIW-UHNVWZDZSA-N

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