(S)-1-(2,3,4,6-Tetra-O-pivaloyl-β-D-galactopyranosyl)-2-(3-pyridyl)pyrrolidine
A
2,3,4,6-Tetra-O-pivaloyl-α/β-D-galactopyranose
B
nornicotine
Conditions | Yield |
---|---|
In hydrogenchloride; methanol Hydrolysis; | A n/a B 95% |
(S)-3-(1-azido-but-3-enyl)pyridine
nornicotine
Conditions | Yield |
---|---|
With bis(cyclohexanyl)borane In tetrahydrofuran at -15 - 20℃; for 12h; | 85% |
nornicotine
Conditions | Yield |
---|---|
Stage #1: (S)-5-bromonornicotine (R)-(+)-α-methoxy-α-trifluoromethylphenyl acetic acid salt With potassium hydroxide In water for 1h; Stage #2: With palladium 10% on activated carbon; hydrogen; triethylamine In ethanol at 20℃; | 69% |
Conditions | Yield |
---|---|
With borane-ammonia complex; 6-hydroxy-D-nicotine oxidase E350L/E352D mutant for 28h; Kinetics; Enzymatic reaction; enantioselective reaction; | 60% |
With 6,6′-dinitro[1,1′-biphenyl]-2,2′-dicarboxylic acid |
Conditions | Yield |
---|---|
bioconversion, by cell suspension of Nicotiana plumbaginifolia; | 53.2% |
With potassium permanganate | |
With water; silver(l) oxide |
nornicotine
Conditions | Yield |
---|---|
Stage #1: (S)-5-bromonornicotine (+)-MTPA With potassium hydroxide In diethyl ether Stage #2: With palladium 10% on activated carbon; hydrogen; triethylamine In ethanol for 1h; | 53% |
Conditions | Yield |
---|---|
With Chiralpak AD-H In methanol; N,N-dimethyl-ethanamine Resolution of racemate; | A 30% B 25% |
nicotin
A
nornicotine
B
S-(-)-Norcotinine
C
cotinine
D
Nicotine-N-oxide
Conditions | Yield |
---|---|
With air; cofactor solution; phenobarbitone-induced rabbit hepatic homogenate In phosphate buffer at 37℃; for 1h; pH=7.4; Oxidation; demethylation; Further byproducts given; | A 15.9% B n/a C 27.5% D n/a |
(S)-5-bromo-3-(1H-2-pyrrolidinyl)pyridine
nornicotine
Conditions | Yield |
---|---|
With triethylamine; palladium on activated charcoal In ethanol under 760 Torr; for 1h; Yield given; | |
With hydrogen | |
With hydrogen; triethylamine; palladium on activated charcoal In ethanol under 760.051 Torr; for 1h; | 621 mg |
Conditions | Yield |
---|---|
In water at 28℃; for 120h; Product distribution; Cunninghamella echinulata IFO-4444; other times, other fungi; |
Conditions | Yield |
---|---|
at 25℃; Nicotiana tabacum L. cv Wisconsin-38; |
1-(N-methyl)-1,5-pentanediamine
A
N-methylanabasine
B
nornicotine
C
nicotin
D
anatabine
Conditions | Yield |
---|---|
With Nicotiana rustica Condensation; Enzymatic reaction; Further byproducts given; |
N-ethylcadaverine
A
N-ethylanabasine
B
nornicotine
C
nicotin
D
anatabine
Conditions | Yield |
---|---|
With Nicotiana rustica Condensation; Enzymatic reaction; Further byproducts given; |
N-(4-aminobutyl)propylamine
A
nornicotine
B
nicotin
C
anatabine
Conditions | Yield |
---|---|
With Nicotiana rustica Condensation; Enzymatic reaction; Further byproducts given; |
Conditions | Yield |
---|---|
With Nicotiana rustica Condensation; Enzymatic reaction; Further byproducts given; |
Conditions | Yield |
---|---|
With Nicotiana rustica Condensation; Enzymatic reaction; Further byproducts given; |
5-bromopyridine-3-carbaldehyde
nornicotine
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 97 percent / Zn / tetrahydrofuran / 1 h / 20 °C 2: 100 percent / DMP / CH2Cl2 / 0.5 h / 20 °C 3: (+)-B-chlorodiisopinocampheylborane / tetrahydrofuran / -30 °C 4: 100 percent / Et3N / CH2Cl2 / 0.17 h / 0 °C 5: 83 percent / NaN3 / dimethylformamide / 4 h / 60 °C 6: 62 percent / cyclohexene; BH3*Me2S / tetrahydrofuran / 12 h / -15 - 20 °C 7: H2 View Scheme | |
Multi-step reaction with 6 steps 1.1: DMP / CH2Cl2 1.2: tetrahydrofuran 2.1: (+)-B-chlorodiisopinocampheylborane / tetrahydrofuran / -30 °C 3.1: 100 percent / Et3N / CH2Cl2 / 0.17 h / 0 °C 4.1: 83 percent / NaN3 / dimethylformamide / 4 h / 60 °C 5.1: 62 percent / cyclohexene; BH3*Me2S / tetrahydrofuran / 12 h / -15 - 20 °C 6.1: H2 View Scheme | |
Multi-step reaction with 5 steps 1: diethyl ether / 1 h / -100 °C 2: 100 percent / Et3N / CH2Cl2 / 0.17 h / 0 °C 3: 83 percent / NaN3 / dimethylformamide / 4 h / 60 °C 4: 62 percent / cyclohexene; BH3*Me2S / tetrahydrofuran / 12 h / -15 - 20 °C 5: H2 View Scheme |
5-bromo-3-pyridinecarboxylic acid
nornicotine
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: DMF; oxalyl chloride / acetonitrile; tetrahydrofuran; pyridine / 1.5 h / -30 °C 1.2: 63 percent / CuI; tri-tert-butoxyaluminium hydride / acetonitrile; tetrahydrofuran; pyridine / 0.25 h / -78 °C 2.1: 97 percent / Zn / tetrahydrofuran / 1 h / 20 °C 3.1: 100 percent / DMP / CH2Cl2 / 0.5 h / 20 °C 4.1: (+)-B-chlorodiisopinocampheylborane / tetrahydrofuran / -30 °C 5.1: 100 percent / Et3N / CH2Cl2 / 0.17 h / 0 °C 6.1: 83 percent / NaN3 / dimethylformamide / 4 h / 60 °C 7.1: 62 percent / cyclohexene; BH3*Me2S / tetrahydrofuran / 12 h / -15 - 20 °C 8.1: H2 View Scheme | |
Multi-step reaction with 7 steps 1.1: DMF; oxalyl chloride / acetonitrile; tetrahydrofuran; pyridine / 1.5 h / -30 °C 1.2: 63 percent / CuI; tri-tert-butoxyaluminium hydride / acetonitrile; tetrahydrofuran; pyridine / 0.25 h / -78 °C 2.1: DMP / CH2Cl2 2.2: tetrahydrofuran 3.1: (+)-B-chlorodiisopinocampheylborane / tetrahydrofuran / -30 °C 4.1: 100 percent / Et3N / CH2Cl2 / 0.17 h / 0 °C 5.1: 83 percent / NaN3 / dimethylformamide / 4 h / 60 °C 6.1: 62 percent / cyclohexene; BH3*Me2S / tetrahydrofuran / 12 h / -15 - 20 °C 7.1: H2 View Scheme | |
Multi-step reaction with 6 steps 1.1: DMF; oxalyl chloride / acetonitrile; tetrahydrofuran; pyridine / 1.5 h / -30 °C 1.2: 63 percent / CuI; tri-tert-butoxyaluminium hydride / acetonitrile; tetrahydrofuran; pyridine / 0.25 h / -78 °C 2.1: diethyl ether / 1 h / -100 °C 3.1: 100 percent / Et3N / CH2Cl2 / 0.17 h / 0 °C 4.1: 83 percent / NaN3 / dimethylformamide / 4 h / 60 °C 5.1: 62 percent / cyclohexene; BH3*Me2S / tetrahydrofuran / 12 h / -15 - 20 °C 6.1: H2 View Scheme |
1-(5-bromopyridin-3-yl)but-3-en-1-ol
nornicotine
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 100 percent / DMP / CH2Cl2 / 0.5 h / 20 °C 2: (+)-B-chlorodiisopinocampheylborane / tetrahydrofuran / -30 °C 3: 100 percent / Et3N / CH2Cl2 / 0.17 h / 0 °C 4: 83 percent / NaN3 / dimethylformamide / 4 h / 60 °C 5: 62 percent / cyclohexene; BH3*Me2S / tetrahydrofuran / 12 h / -15 - 20 °C 6: H2 View Scheme |
1-(5-bromopyridin-3-yl)but-3-en-1-one
nornicotine
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: (+)-B-chlorodiisopinocampheylborane / tetrahydrofuran / -30 °C 2: 100 percent / Et3N / CH2Cl2 / 0.17 h / 0 °C 3: 83 percent / NaN3 / dimethylformamide / 4 h / 60 °C 4: 62 percent / cyclohexene; BH3*Me2S / tetrahydrofuran / 12 h / -15 - 20 °C 5: H2 View Scheme |
(R)-1-(5-bromopyridin-3-yl)but-3-en-1-ol
nornicotine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 100 percent / Et3N / CH2Cl2 / 0.17 h / 0 °C 2: 83 percent / NaN3 / dimethylformamide / 4 h / 60 °C 3: 62 percent / cyclohexene; BH3*Me2S / tetrahydrofuran / 12 h / -15 - 20 °C 4: H2 View Scheme |
(S)-3-(1-azidobut-3-enyl)-5-bromopyridine
nornicotine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 62 percent / cyclohexene; BH3*Me2S / tetrahydrofuran / 12 h / -15 - 20 °C 2: H2 View Scheme |
(R)-methanesulfonic acid 1-(5-bromopyridin-3-yl)but-3-enyl ester
nornicotine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 83 percent / NaN3 / dimethylformamide / 4 h / 60 °C 2: 62 percent / cyclohexene; BH3*Me2S / tetrahydrofuran / 12 h / -15 - 20 °C 3: H2 View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: tetrahydrofuran / 1 h / -100 °C 2: 100 percent / Et3N / CH2Cl2 / 0.17 h / 0 °C 3: 97 percent / NaN3 / dimethylformamide / 4 h / 60 °C 4: 85 percent / dicyclohexylborane / tetrahydrofuran / 12 h / -15 - 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: tetrahydrofuran / 1 h / -100 °C 2: 88 percent / diphenylphosphorylazide; DBU / toluene / 72 h / 20 °C 3: 85 percent / dicyclohexylborane / tetrahydrofuran / 12 h / -15 - 20 °C View Scheme |
(R)-1-(pyridin-3-yl)but-3-en-1-ol
nornicotine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 100 percent / Et3N / CH2Cl2 / 0.17 h / 0 °C 2: 97 percent / NaN3 / dimethylformamide / 4 h / 60 °C 3: 85 percent / dicyclohexylborane / tetrahydrofuran / 12 h / -15 - 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: 88 percent / diphenylphosphorylazide; DBU / toluene / 72 h / 20 °C 2: 85 percent / dicyclohexylborane / tetrahydrofuran / 12 h / -15 - 20 °C View Scheme |
(R)-methanesulfonic acid 1-pyridin-3-yl-but-3-enyl ester
nornicotine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 97 percent / NaN3 / dimethylformamide / 4 h / 60 °C 2: 85 percent / dicyclohexylborane / tetrahydrofuran / 12 h / -15 - 20 °C View Scheme |
4-(3-pyridyl)-4-oxobutanol
nornicotine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: 82 percent / (COCl)2; NEt3 / dimethylsulfoxide 2.1: molecular sieves 4 Angstroem / CH2Cl2 / 16 h / 20 °C 2.2: 45 percent / NaCNBH3 / methanol; acetic acid / 16 h / 0 - 20 °C 3.1: 95 percent / aq. HCl; methanol View Scheme |
4-Oxo-1-(3-pyridyl)-1-butanone
nornicotine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: molecular sieves 4 Angstroem / CH2Cl2 / 16 h / 20 °C 1.2: 45 percent / NaCNBH3 / methanol; acetic acid / 16 h / 0 - 20 °C 2.1: 95 percent / aq. HCl; methanol View Scheme |
ethyl 5-bromo-3-pyridinecarboxylate
nornicotine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 2: 79 percent / NaBH4 / methanol; acetic acid / -40 - -20 °C 4: Et3N / 10percent Pd/C / ethanol / 1 h / 760 Torr View Scheme | |
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran 2.1: sodium tetrahydroborate; acetic acid; methanol 2.2: Resolution of racemate 3.1: potassium hydroxide / diethyl ether View Scheme | |
Multi-step reaction with 4 steps 1.1: sodium hydride / mineral oil; hexane; tetrahydrofuran / 1 h / Reflux; Inert atmosphere 1.2: Reflux 2.1: acetic acid; sodium tetrahydroborate / methanol; acetonitrile / 0.17 h / -40 - 20 °C 3.1: ethyl acetate / 0.25 h 4.1: potassium hydroxide / diethyl ether 4.2: 1 h View Scheme | |
Multi-step reaction with 4 steps 1.1: sodium hydride / mineral oil; tetrahydrofuran / 1 h / Reflux; Inert atmosphere 1.2: Reflux; Inert atmosphere 2.1: acetic acid; sodium tetrahydroborate / methanol / 0.5 h / -40 - 20 °C 3.1: ethyl acetate / 0.25 h / 20 °C 4.1: potassium hydroxide / water / 1 h 4.2: 20 °C View Scheme |
5-Bromo-3-(2-pyrrolidinyl)pyridine
nornicotine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 2: Et3N / 10percent Pd/C / ethanol / 1 h / 760 Torr View Scheme | |
Multi-step reaction with 2 steps 1.1: ethyl acetate / 0.25 h 2.1: potassium hydroxide / diethyl ether 2.2: 1 h View Scheme | |
Multi-step reaction with 2 steps 1.1: ethyl acetate / 0.25 h / 20 °C 2.1: potassium hydroxide / water / 1 h 2.2: 20 °C View Scheme |
methyl 4-iodobutanoate
nornicotine
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 18h; | 78% |
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 18h; | 78% |
methyl 6-iodohexanoate
nornicotine
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 18h; | 75% |
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 18h; | 75% |
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 20℃; for 15h; Inert atmosphere; | 74% |
methyl trans-γ-iodocrotonate
nornicotine
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 18h; | 73% |
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 18h; | 73% |
3-chloro-4-(4-formylphenoxy)benzamide
nornicotine
(S)-3-chloro-4-(4-((2-(pyridin-3-yl)pyrrolidin-1-yl)methyl)phenoxy)benzamide
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 20℃; | 68% |
(6-iodohexyl)-carbamic acid 1,1-dimethylethyl ester
nornicotine
[6-[(2S)-2-(3-pyridinyl)-1-pyrrolidinyl]hexyl]-carbamic acid 1,1-dimethylethyl ester
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 15h; | 59% |
benzyl 4-iodobutanoate
nornicotine
(2S)-2-(3-pyridinyl)-1-pyrrolidinebutanoic acid phenylmethyl ester
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; | 58% |
nornicotine
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 18h; | 51% |
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 18h; | 51% |
nornicotine
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 18h; | 49% |
Empirical Formula: C9H12N2
Molecular Weight: 148.205 g/mol
Index of Refraction: 1.536
Density: 1.042 g/cm3
Flash Point: 111.3 °C
Enthalpy of Vaporization: 50.82 kJ/mol
Boiling Point: 270 °C at 760 mmHg
Vapour Pressure: 0.00702 mmHg at 25 °C
Structure of Nornicotine (CAS NO.494-97-3):
IUPAC Name of Nornicotine (CAS NO.494-97-3): 3-Pyrrolidin-2-ylpyridine
Product Categories of Nornicotine (CAS NO.494-97-3): Pharmacetical
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 14660ug/kg (14.66mg/kg) | Nara Igaku Zasshi. Journal of the Nara Medical Association. Vol. 8, Pg. 69, 1957. | |
mouse | LD50 | intravenous | 3409ug/kg (3.409mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 88, Pg. 82, 1946. | |
rabbit | LD50 | intraperitoneal | > 13700ug/kg (13.7mg/kg) | Proceedings of the Society for Experimental Biology and Medicine. Vol. 58, Pg. 231, 1945. | |
rabbit | LD50 | intravenous | 3mg/kg (3mg/kg) | Proceedings of the Society for Experimental Biology and Medicine. Vol. 58, Pg. 231, 1945. | |
rat | LDLo | intraperitoneal | 23500ug/kg (23.5mg/kg) | "Merck Index; an Encyclopedia of Chemicals, Drugs, and Biologicals", 11th ed., Rahway, NJ 07065, Merck & Co., Inc. 1989Vol. 11, Pg. 1061, 1989. |
Poison by intraperitoneal and intravenous routes. About 1/3 the toxicity of nicotine. Causes faintness, prostration, muscular weakness, severe nausea, vomiting, diarrhea, and collapse without convulsions. An insecticide. When heated to decomposition it emits highly toxic fumes of NOx.
Nornicotine ,its cas register number is 494-97-3. It also can be called 3-(2-Pyrrolidinyl)pyridine ; Pyridine, 3-(2-pyrrolidinyl)- ;and 3-(Pyrrolidin-2-yl)pyridine .
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