Product Name

  • Name

    VASICINE

  • EINECS 228-180-8
  • CAS No. 6159-55-3
  • Article Data2
  • CAS DataBase
  • Density 1.37 g/cm3
  • Solubility
  • Melting Point 182 ºC
  • Formula C11H12 N2 O
  • Boiling Point 373.8 °C at 760 mmHg
  • Molecular Weight 188.229
  • Flash Point 179.9 °C
  • Transport Information
  • Appearance
  • Safety Poison by ingestion, intraperitoneal, and subcutaneous routes. Experimental reproductive effects. When heated to decomposition it emits toxic fumes of NOx.
  • Risk Codes 22
  • Molecular Structure Molecular Structure of 6159-55-3 (VASICINE)
  • Hazard Symbols Xn
  • Synonyms Pyrrolo[2,1-b]quinazolin-3-ol,1,2,3,9-tetrahydro-, (S)-;Vasicine (6CI,7CI,8CI);(-)-Linarine;(-)-Peganine;(-)-Vasicine;Linarine, (-)-;Peganin;Peganine;Peganine, (-)-;l-Peganine;l-Vasicine;
  • PSA 35.83000
  • LogP 0.67030

Synthetic route

vasicine
6159-56-4, 176200-11-6

vasicine

(+)-vasicinol
6159-55-3

(+)-vasicinol

Conditions
ConditionsYield
With D-tartaric acid
vasicine
6159-56-4, 176200-11-6

vasicine

A

vasicine
18549-38-7

vasicine

B

(+)-vasicinol
6159-55-3

(+)-vasicinol

Conditions
ConditionsYield
With 2,2'-iminobis[ethanol] In ethanol Resolution of racemate;
(+)-vasicinol
6159-55-3

(+)-vasicinol

(3S)-1-[(2-aminophenyll)methyl]pyrrolidin-3-ol
1227263-77-5

(3S)-1-[(2-aminophenyll)methyl]pyrrolidin-3-ol

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol; water for 2h; Solvent;99%
With sodium tetrahydroborate In methanol; water at 20℃; for 2h;99%
With sodium tetrahydroborate; water In methanol at 20℃;90%
(+)-vasicinol
6159-55-3

(+)-vasicinol

(3S)-1,2,3,3a,4,9-hexahydropyrrolo[2,1-b]quinazolin-3-ol

(3S)-1,2,3,3a,4,9-hexahydropyrrolo[2,1-b]quinazolin-3-ol

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol at 20℃; for 1h; Solvent;95%
(+)-vasicinol
6159-55-3

(+)-vasicinol

A

(3S)-1-[(2-aminophenyll)methyl]pyrrolidin-3-ol
1227263-77-5

(3S)-1-[(2-aminophenyll)methyl]pyrrolidin-3-ol

B

(3S)-1,2,3,3a,4,9-hexahydropyrrolo[2,1-b]quinazolin-3-ol

(3S)-1,2,3,3a,4,9-hexahydropyrrolo[2,1-b]quinazolin-3-ol

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol; water for 2h; Solvent;A 80%
B 10%
(S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride
39637-99-5, 20445-33-4

(S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride

(+)-vasicinol
6159-55-3

(+)-vasicinol

vasicine (R)-α-methoxy-α-(trifluoromethyl)phenylacetic acid ester

vasicine (R)-α-methoxy-α-(trifluoromethyl)phenylacetic acid ester

(R)-methoxytrifluoromethylphenylacetyl chloride
20445-33-4, 39637-99-5

(R)-methoxytrifluoromethylphenylacetyl chloride

(+)-vasicinol
6159-55-3

(+)-vasicinol

vasicine (S)-α-methoxy-α-(trifluoromethyl)phenylacetic acid ester

vasicine (S)-α-methoxy-α-(trifluoromethyl)phenylacetic acid ester

(+)-vasicinol
6159-55-3

(+)-vasicinol

(R)-N-benzyl-3-hydroxypyrrolidine
101385-90-4, 101930-07-8, 101979-03-7, 775-15-5

(R)-N-benzyl-3-hydroxypyrrolidine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: water; sodium tetrahydroborate / methanol / 10 h / 20 °C
2.1: hypophosphorous acid; sodium azide; sulfuric acid; acetic acid / water / 39.5 h / 5 °C
2.2: pH 8
3.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere
3.2: 16 h / 20 °C / Inert atmosphere
4.1: water; lithium hydroxide monohydrate / tetrahydrofuran; methanol / 2 h / 0 °C
View Scheme
Multi-step reaction with 4 steps
1.1: sodium tetrahydroborate / methanol; water / 2 h
2.1: isopentyl nitrite / N,N-dimethyl-formamide / 0.5 h / 65 °C
3.1: diethylazodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere
3.2: 16 h / 20 °C / Inert atmosphere
4.1: lithium hydroxide monohydrate / methanol; tetrahydrofuran / 2 h / 0 °C
View Scheme
Multi-step reaction with 4 steps
1.1: sodium tetrahydroborate / methanol; water / 2 h
2.1: isopentyl nitrite / N,N-dimethyl-formamide / 0.5 h / 65 °C
3.1: diethylazodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere
3.2: 16 h / 20 °C / Inert atmosphere
4.1: lithium hydroxide monohydrate / methanol; tetrahydrofuran / 2 h / 0 °C
View Scheme
(+)-vasicinol
6159-55-3

(+)-vasicinol

(S)-N-benzyl-3-hydroxypyrrolidine
101385-90-4

(S)-N-benzyl-3-hydroxypyrrolidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: water; sodium tetrahydroborate / methanol / 10 h / 20 °C
2.1: hypophosphorous acid; sodium azide; sulfuric acid; acetic acid / water / 39.5 h / 5 °C
2.2: pH 8
View Scheme
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / methanol; water / 2 h
2: isopentyl nitrite / N,N-dimethyl-formamide / 0.5 h / 65 °C
View Scheme
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / methanol; water / 2 h
2: isopentyl nitrite / N,N-dimethyl-formamide / 0.5 h / 65 °C
View Scheme
(+)-vasicinol
6159-55-3

(+)-vasicinol

(3R)-1-(phenylmethyl)pyrrolidin-3-ol Acetate
116143-02-3

(3R)-1-(phenylmethyl)pyrrolidin-3-ol Acetate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: water; sodium tetrahydroborate / methanol / 10 h / 20 °C
2.1: hypophosphorous acid; sodium azide; sulfuric acid; acetic acid / water / 39.5 h / 5 °C
2.2: pH 8
3.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere
3.2: 16 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: sodium tetrahydroborate / methanol; water / 2 h
2.1: isopentyl nitrite / N,N-dimethyl-formamide / 0.5 h / 65 °C
3.1: diethylazodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere
3.2: 16 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: sodium tetrahydroborate / methanol; water / 2 h
2.1: isopentyl nitrite / N,N-dimethyl-formamide / 0.5 h / 65 °C
3.1: diethylazodicarboxylate; triphenylphosphine / tetrahydrofuran / 0.33 h / 0 °C / Inert atmosphere
3.2: 16 h / 20 °C / Inert atmosphere
View Scheme
(+)-vasicinol
6159-55-3

(+)-vasicinol

3-chloro-3-deoxyvasicine

3-chloro-3-deoxyvasicine

Conditions
ConditionsYield
With POCl3#PCl5
(+)-vasicinol
6159-55-3

(+)-vasicinol

deoxypeganine
495-59-0

deoxypeganine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: POCl3#PCl5
2:
View Scheme
(+)-vasicinol
6159-55-3

(+)-vasicinol

(S)-3-hydroxy-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one
486-64-6

(S)-3-hydroxy-2,3-dihydropyrrolo[2,1-b]quinazolin-9(1H)-one

Conditions
ConditionsYield
With dihydrogen peroxide In acetone
(+)-vasicinol
6159-55-3

(+)-vasicinol

2-[(3-chloropyrrolidin-1-yl)methyl]benzenamine

2-[(3-chloropyrrolidin-1-yl)methyl]benzenamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: POCl3#PCl5
2: sodium tetrahydroborate / methanol; water / 2 h
View Scheme
(+)-vasicinol
6159-55-3

(+)-vasicinol

2-(pyrrolidin-1-ylmethyl)benzenamine
55727-59-8

2-(pyrrolidin-1-ylmethyl)benzenamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: POCl3#PCl5
2:
3: sodium tetrahydroborate / methanol; water / 2 h
View Scheme
(+)-vasicinol
6159-55-3

(+)-vasicinol

(R)-(3-(4-(4-fluorophenyl)-1H-1,2,3-triazol-1-yl)pyrrolidin-1-yl)(2-(pyridin-4-ylamino)phenyl)methanone

(R)-(3-(4-(4-fluorophenyl)-1H-1,2,3-triazol-1-yl)pyrrolidin-1-yl)(2-(pyridin-4-ylamino)phenyl)methanone

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: sodium tetrahydroborate; methanol / water
2.1: potassium carbonate / toluene / 6 h / Reflux
3.1: 1H-imidazole / dichloromethane / 20 h / 20 °C
4.1: benzyl(triethyl)ammoniumpermanganate / dichloromethane / 4 h / Reflux
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C
6.1: tetrahydrofuran / 5 h / 25 °C
7.1: triethylamine; dmap; p-toluenesulfonyl chloride / dichloromethane / 12.5 h / 0 - 15 °C
7.2: 4 h / 60 °C
7.3: 1 h / Acidic conditions
8.1: copper(II) sulfate; sodium L-ascorbate / water; tert-butyl alcohol / 6 h / 50 - 60 °C
View Scheme
(+)-vasicinol
6159-55-3

(+)-vasicinol

(R)-(3-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolidin-1-yl)(2-(pyridin-4-ylamino)phenyl)methanone

(R)-(3-(4-phenyl-1H-1,2,3-triazol-1-yl)pyrrolidin-1-yl)(2-(pyridin-4-ylamino)phenyl)methanone

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: sodium tetrahydroborate; methanol / water
2.1: potassium carbonate / toluene / 6 h / Reflux
3.1: 1H-imidazole / dichloromethane / 20 h / 20 °C
4.1: benzyl(triethyl)ammoniumpermanganate / dichloromethane / 4 h / Reflux
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C
6.1: tetrahydrofuran / 5 h / 25 °C
7.1: triethylamine; dmap; p-toluenesulfonyl chloride / dichloromethane / 12.5 h / 0 - 15 °C
7.2: 4 h / 60 °C
7.3: 1 h / Acidic conditions
8.1: copper(II) sulfate; sodium L-ascorbate / water; tert-butyl alcohol / 6 h / 50 - 60 °C
View Scheme
(+)-vasicinol
6159-55-3

(+)-vasicinol

(R)-(3-(4-hexyl-1H-1,2,3-triazol-1-yl)pyrrolidin-1-yl)(2-(pyridin-4-ylamino)phenyl)methanone

(R)-(3-(4-hexyl-1H-1,2,3-triazol-1-yl)pyrrolidin-1-yl)(2-(pyridin-4-ylamino)phenyl)methanone

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: sodium tetrahydroborate; methanol / water
2.1: potassium carbonate / toluene / 6 h / Reflux
3.1: 1H-imidazole / dichloromethane / 20 h / 20 °C
4.1: benzyl(triethyl)ammoniumpermanganate / dichloromethane / 4 h / Reflux
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C
6.1: tetrahydrofuran / 5 h / 25 °C
7.1: triethylamine; dmap; p-toluenesulfonyl chloride / dichloromethane / 12.5 h / 0 - 15 °C
7.2: 4 h / 60 °C
7.3: 1 h / Acidic conditions
8.1: copper(II) sulfate; sodium L-ascorbate / water; tert-butyl alcohol / 6 h / 50 - 60 °C
View Scheme
(+)-vasicinol
6159-55-3

(+)-vasicinol

(R)-(3-(4-(4-pentylphenyl)-1H-1,2,3-triazol-1-yl)pyrrolidin-1-yl)(2-(pyridin-4-ylamino)phenyl)methanone

(R)-(3-(4-(4-pentylphenyl)-1H-1,2,3-triazol-1-yl)pyrrolidin-1-yl)(2-(pyridin-4-ylamino)phenyl)methanone

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: sodium tetrahydroborate; methanol / water
2.1: potassium carbonate / toluene / 6 h / Reflux
3.1: 1H-imidazole / dichloromethane / 20 h / 20 °C
4.1: benzyl(triethyl)ammoniumpermanganate / dichloromethane / 4 h / Reflux
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C
6.1: tetrahydrofuran / 5 h / 25 °C
7.1: triethylamine; dmap; p-toluenesulfonyl chloride / dichloromethane / 12.5 h / 0 - 15 °C
7.2: 4 h / 60 °C
7.3: 1 h / Acidic conditions
8.1: copper(II) sulfate; sodium L-ascorbate / water; tert-butyl alcohol / 6 h / 50 - 60 °C
View Scheme
(+)-vasicinol
6159-55-3

(+)-vasicinol

(R)-(3-(4-pentyl-1H-1,2,3-triazol-1-yl)pyrrolidin-1-yl)(2-(pyridin-4-ylamino)phenyl)methanone

(R)-(3-(4-pentyl-1H-1,2,3-triazol-1-yl)pyrrolidin-1-yl)(2-(pyridin-4-ylamino)phenyl)methanone

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: sodium tetrahydroborate; methanol / water
2.1: potassium carbonate / toluene / 6 h / Reflux
3.1: 1H-imidazole / dichloromethane / 20 h / 20 °C
4.1: benzyl(triethyl)ammoniumpermanganate / dichloromethane / 4 h / Reflux
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C
6.1: tetrahydrofuran / 5 h / 25 °C
7.1: triethylamine; dmap; p-toluenesulfonyl chloride / dichloromethane / 12.5 h / 0 - 15 °C
7.2: 4 h / 60 °C
7.3: 1 h / Acidic conditions
8.1: copper(II) sulfate; sodium L-ascorbate / water; tert-butyl alcohol / 6 h / 50 - 60 °C
View Scheme
(+)-vasicinol
6159-55-3

(+)-vasicinol

(R)-(3-(4-propyl-1H-1,2,3-triazol-1-yl)pyrrolidin-1-yl)(2-(pyridin-4-ylamino)phenyl)methanone

(R)-(3-(4-propyl-1H-1,2,3-triazol-1-yl)pyrrolidin-1-yl)(2-(pyridin-4-ylamino)phenyl)methanone

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: sodium tetrahydroborate; methanol / water
2.1: potassium carbonate / toluene / 6 h / Reflux
3.1: 1H-imidazole / dichloromethane / 20 h / 20 °C
4.1: benzyl(triethyl)ammoniumpermanganate / dichloromethane / 4 h / Reflux
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C
6.1: tetrahydrofuran / 5 h / 25 °C
7.1: triethylamine; dmap; p-toluenesulfonyl chloride / dichloromethane / 12.5 h / 0 - 15 °C
7.2: 4 h / 60 °C
7.3: 1 h / Acidic conditions
8.1: copper(II) sulfate; sodium L-ascorbate / water; tert-butyl alcohol / 6 h / 50 - 60 °C
View Scheme
(+)-vasicinol
6159-55-3

(+)-vasicinol

(S)-1-(2-(pyridin-4-ylamino)benzyl)pyrrolidin-3-ol

(S)-1-(2-(pyridin-4-ylamino)benzyl)pyrrolidin-3-ol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium tetrahydroborate; methanol / water
2: potassium carbonate / toluene / 6 h / Reflux
View Scheme
(+)-vasicinol
6159-55-3

(+)-vasicinol

(2-((3-((tert-butyldimethylsilyl)oxy)pyrrolidin-1-yl)methyl)phenyl)pyridin-4-amine

(2-((3-((tert-butyldimethylsilyl)oxy)pyrrolidin-1-yl)methyl)phenyl)pyridin-4-amine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium tetrahydroborate; methanol / water
2: potassium carbonate / toluene / 6 h / Reflux
3: 1H-imidazole / dichloromethane / 20 h / 20 °C
View Scheme
(+)-vasicinol
6159-55-3

(+)-vasicinol

(S)-(3-((tertbutyldimethylsilyl)oxy)pyrrolidin-1-yl)(2-(pyridin-4-ylamino)phenyl)methanone

(S)-(3-((tertbutyldimethylsilyl)oxy)pyrrolidin-1-yl)(2-(pyridin-4-ylamino)phenyl)methanone

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium tetrahydroborate; methanol / water
2: potassium carbonate / toluene / 6 h / Reflux
3: 1H-imidazole / dichloromethane / 20 h / 20 °C
4: benzyl(triethyl)ammoniumpermanganate / dichloromethane / 4 h / Reflux
View Scheme
(+)-vasicinol
6159-55-3

(+)-vasicinol

(S)-(3-hydroxypyrrolidin-1-yl)(2-(pyridin-4-ylamino)phenyl)methanone

(S)-(3-hydroxypyrrolidin-1-yl)(2-(pyridin-4-ylamino)phenyl)methanone

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: sodium tetrahydroborate; methanol / water
2: potassium carbonate / toluene / 6 h / Reflux
3: 1H-imidazole / dichloromethane / 20 h / 20 °C
4: benzyl(triethyl)ammoniumpermanganate / dichloromethane / 4 h / Reflux
5: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C
View Scheme
(+)-vasicinol
6159-55-3

(+)-vasicinol

(S)-tert-butyl(2-(3-hydroxypyrrolidine-1-carbonyl)phenyl)(pyridin-4-yl)carbamate

(S)-tert-butyl(2-(3-hydroxypyrrolidine-1-carbonyl)phenyl)(pyridin-4-yl)carbamate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: sodium tetrahydroborate; methanol / water
2: potassium carbonate / toluene / 6 h / Reflux
3: 1H-imidazole / dichloromethane / 20 h / 20 °C
4: benzyl(triethyl)ammoniumpermanganate / dichloromethane / 4 h / Reflux
5: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C
6: tetrahydrofuran / 5 h / 25 °C
View Scheme
(+)-vasicinol
6159-55-3

(+)-vasicinol

(R)-(3-azidopyrrolidin-1-yl)(2-(pyridin-4-ylamino)phenyl)methanone

(R)-(3-azidopyrrolidin-1-yl)(2-(pyridin-4-ylamino)phenyl)methanone

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: sodium tetrahydroborate; methanol / water
2.1: potassium carbonate / toluene / 6 h / Reflux
3.1: 1H-imidazole / dichloromethane / 20 h / 20 °C
4.1: benzyl(triethyl)ammoniumpermanganate / dichloromethane / 4 h / Reflux
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C
6.1: tetrahydrofuran / 5 h / 25 °C
7.1: triethylamine; dmap; p-toluenesulfonyl chloride / dichloromethane / 12.5 h / 0 - 15 °C
7.2: 4 h / 60 °C
7.3: 1 h / Acidic conditions
View Scheme
(+)-vasicinol
6159-55-3

(+)-vasicinol

(R)-(3-(4-cyclopropyl-1H-1,2,3-triazol-1-yl)pyrrolidin-1-yl)(2-(pyridin-4-ylamino)phenyl)methanone

(R)-(3-(4-cyclopropyl-1H-1,2,3-triazol-1-yl)pyrrolidin-1-yl)(2-(pyridin-4-ylamino)phenyl)methanone

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: sodium tetrahydroborate; methanol / water
2.1: potassium carbonate / toluene / 6 h / Reflux
3.1: 1H-imidazole / dichloromethane / 20 h / 20 °C
4.1: benzyl(triethyl)ammoniumpermanganate / dichloromethane / 4 h / Reflux
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C
6.1: tetrahydrofuran / 5 h / 25 °C
7.1: triethylamine; dmap; p-toluenesulfonyl chloride / dichloromethane / 12.5 h / 0 - 15 °C
7.2: 4 h / 60 °C
7.3: 1 h / Acidic conditions
8.1: copper(II) sulfate; sodium L-ascorbate / water; tert-butyl alcohol / 6 h / 50 - 60 °C
View Scheme
(+)-vasicinol
6159-55-3

(+)-vasicinol

(S)-methyl-9-((2-((3-hydroxypyrrolidin-1-yl)methyl)phenyl)-amino)-9-oxononanoate

(S)-methyl-9-((2-((3-hydroxypyrrolidin-1-yl)methyl)phenyl)-amino)-9-oxononanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / methanol; water / 2 h / 20 °C
2: boric acid / toluene / 3 h / Molecular sieve; Inert atmosphere; Reflux
View Scheme
(+)-vasicinol
6159-55-3

(+)-vasicinol

(S)-methyl-5-((2-((3-hydroxypyrrolidin-1-yl)methyl)phenyl)-amino)-5-oxopentanoate

(S)-methyl-5-((2-((3-hydroxypyrrolidin-1-yl)methyl)phenyl)-amino)-5-oxopentanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / methanol; water / 2 h / 20 °C
2: boric acid / toluene / 3 h / Molecular sieve; Inert atmosphere; Reflux
View Scheme
(+)-vasicinol
6159-55-3

(+)-vasicinol

(S)-methyl 6-((2-((3-hydroxypyrrolidin-1-yl)methyl)phenyl)-amino)-6-oxohexanoate

(S)-methyl 6-((2-((3-hydroxypyrrolidin-1-yl)methyl)phenyl)-amino)-6-oxohexanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium tetrahydroborate / methanol; water / 2 h / 20 °C
2: boric acid / toluene / 3 h / Molecular sieve; Inert atmosphere; Reflux
View Scheme

Vasicine Specification

Vasicine, with the CAS NO.6159-55-3, is also called 1-b)quinazolin-3-ol,1,2,3,9-tetrahydro-pyrrolo(; vasicin; 1,2,3,9-TETRAHYDROPYRROLO[2,1-B]QUINAZOLIN-3-OL; AKOS NCG1-0080; VITAS-BB TBB000541; VASICINE; PEGANINE; C10733. It belongs to the Product Categories of Miscellaneous Natural Products. It is a white to yellow powder and is found in the leaves of the Malabar nut and seeds of the harmal and is thought to poison lower plants and animals but not higher animals.

Physical properties about Vasicine are: (1)ACD/LogP: -0.206; (2)ACD/LogD (pH 5.5): -2.19; (3)ACD/LogD (pH 7.4): -1.72; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 1.00; (7)ACD/KOC (pH 7.4): 1.00; (8)#H bond acceptors: 3; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 1; (11)Index of Refraction: 1.709; (12)Molar Refractivity: 53.452 cm3; (13)Molar Volume: 136.881 cm3; (14)Polarizability: 21.19 10-24cm3; (15)Surface Tension: 55.8619995117188 dyne/cm; (16)Density: 1.375 g/cm3; (17)Flash Point: 179.891 °C; (18)Enthalpy of Vaporization: 65.528 kJ/mol; (19)Boiling Point: 373.837 °C at 760 mmHg

You can still convert the following datas into molecular structure:
(1)InChI=1S/C11H12N2O/c14-10-5-6-13-7-8-3-1-2-4-9(8)12-11(10)13/h1-4,10,14H,5-7H2/t10-/m0/s1;
(2)InChIKey=YIICVSCAKJMMDJ-JTQLQIEISA-N;
(3)SmilesN1=C2N(Cc3ccccc13)CC[C@@H]2O

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo subcutaneous 100mg/kg (100mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: EXCITEMENT		 Pharmacology and Toxicology. English translation of FATOAO. Vol. 22, Pg. 67, 1959.
mouse LD50 intraperitoneal 79mg/kg (79mg/kg)   Indian Journal of Medical Research. Vol. 66, Pg. 680, 1977.
mouse LD50 intravenous 79mg/kg (79mg/kg)   Pharmacology and Toxicology. English translation of FATOAO. Vol. 22, Pg. 67, 1959.
rabbit LDLo intravenous 75mg/kg (75mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: ATAXIA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Pharmacology and Toxicology. English translation of FATOAO. Vol. 22, Pg. 67, 1959.

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