coptisine
Conditions | Yield |
---|---|
With methanesulfonyl chloride; triethylamine In dichloromethane at 20℃; for 6h; | 74% |
Conditions | Yield |
---|---|
Multistep reaction; |
Conditions | Yield |
---|---|
With potassium hydroxide In dimethyl sulfoxide at 40 - 90℃; for 5h; Inert atmosphere; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: oxalyl dichloride / chloroform / 1 h / Reflux 2: dimethyl sulfoxide / 25.5 h / 115 - 120 °C View Scheme |
N-Methyl-dihydrocoptisinium-Kation
coptisine
Conditions | Yield |
---|---|
In dimethyl sulfoxide at 115 - 120℃; for 25.5h; |
Dihydrocoptisine
coptisine
Conditions | Yield |
---|---|
With iodine; potassium acetate In ethanol at 20℃; Inert atmosphere; | 5.5 mg |
5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinoline
coptisine
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: copper(l) iodide; benzoic acid / toluene / 12 h / 80 °C / Inert atmosphere; Molecular sieve 2: potassium carbonate / methanol / 0.5 h / 20 °C / Inert atmosphere 3: sodium formate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide; water / 1 h / 100 °C / Inert atmosphere 4: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile / 2 h / 50 °C / Inert atmosphere; Molecular sieve 5: Wilkinson's catalyst; diphenyl phosphoryl azide / diethylene glycol dimethyl ether / 12 h / 160 °C / Inert atmosphere 6: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere 7: potassium acetate; iodine / ethanol / 20 °C / Inert atmosphere View Scheme |
coptisine
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: sodium formate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide; water / 1 h / 100 °C / Inert atmosphere 2: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile / 2 h / 50 °C / Inert atmosphere; Molecular sieve 3: Wilkinson's catalyst; diphenyl phosphoryl azide / diethylene glycol dimethyl ether / 12 h / 160 °C / Inert atmosphere 4: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere 5: potassium acetate; iodine / ethanol / 20 °C / Inert atmosphere View Scheme |
5-bromo-benzo[1,3]dioxole-4-carbaldehyde
coptisine
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: copper(l) iodide; benzoic acid / toluene / 12 h / 80 °C / Inert atmosphere; Molecular sieve 2: potassium carbonate / methanol / 0.5 h / 20 °C / Inert atmosphere 3: sodium formate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide; water / 1 h / 100 °C / Inert atmosphere 4: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile / 2 h / 50 °C / Inert atmosphere; Molecular sieve 5: Wilkinson's catalyst; diphenyl phosphoryl azide / diethylene glycol dimethyl ether / 12 h / 160 °C / Inert atmosphere 6: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere 7: potassium acetate; iodine / ethanol / 20 °C / Inert atmosphere View Scheme |
coptisine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile / 2 h / 50 °C / Inert atmosphere; Molecular sieve 2: Wilkinson's catalyst; diphenyl phosphoryl azide / diethylene glycol dimethyl ether / 12 h / 160 °C / Inert atmosphere 3: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere 4: potassium acetate; iodine / ethanol / 20 °C / Inert atmosphere View Scheme |
coptisine
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: potassium carbonate / methanol / 0.5 h / 20 °C / Inert atmosphere 2: sodium formate; tetrakis(triphenylphosphine) palladium(0) / N,N-dimethyl-formamide; water / 1 h / 100 °C / Inert atmosphere 3: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / acetonitrile / 2 h / 50 °C / Inert atmosphere; Molecular sieve 4: Wilkinson's catalyst; diphenyl phosphoryl azide / diethylene glycol dimethyl ether / 12 h / 160 °C / Inert atmosphere 5: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere 6: potassium acetate; iodine / ethanol / 20 °C / Inert atmosphere View Scheme |
coptisine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: Wilkinson's catalyst; diphenyl phosphoryl azide / diethylene glycol dimethyl ether / 12 h / 160 °C / Inert atmosphere 2: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere 3: potassium acetate; iodine / ethanol / 20 °C / Inert atmosphere View Scheme |
coptisinone
coptisine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 2 h / Reflux; Inert atmosphere 2: potassium acetate; iodine / ethanol / 20 °C / Inert atmosphere View Scheme |
coptisine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: potassium carbonate / dimethyl sulfoxide / 90 °C / Inert atmosphere 2: sodium carbonate; tris-(dibenzylideneacetone)dipalladium(0); XPhos / toluene; ethanol / 12 h / 110 °C / Inert atmosphere 3: triethylamine; methanesulfonyl chloride / dichloromethane / 6 h / 20 °C View Scheme |
coptisine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: sodium carbonate; tris-(dibenzylideneacetone)dipalladium(0); XPhos / toluene; ethanol / 12 h / 110 °C / Inert atmosphere 2: triethylamine; methanesulfonyl chloride / dichloromethane / 6 h / 20 °C View Scheme |
coptisine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: boron tribromide / dichloromethane / 2 h / -78 - -30 °C / Inert atmosphere 2: potassium carbonate / dimethyl sulfoxide / 90 °C / Inert atmosphere 3: sodium carbonate; tris-(dibenzylideneacetone)dipalladium(0); XPhos / toluene; ethanol / 12 h / 110 °C / Inert atmosphere 4: triethylamine; methanesulfonyl chloride / dichloromethane / 6 h / 20 °C View Scheme |
Conditions | Yield |
---|---|
With sodium hydroxide at 20℃; for 1h; | 69.8% |
coptisine
C19H13NO5
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride 1.) THF; 2.) benzene; Yield given. Multistep reaction; |
coptisine
C20H15NO5
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) LiAlH4 / 1.) THF; 2.) benzene 2: 1.) 25percent KOH; 2.) m-chloroperoxybenzoic acid / 1.) MeOH; 2.) CH2Cl2 View Scheme |
coptisine
(6S,7S)-8-Methyl-7-(6-vinyl-benzo[1,3]dioxol-5-yl)-6,7,8,9-tetrahydro-[1,3]dioxolo[4,5-h]isoquinolin-6-ol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.) LiAlH4 / 1.) THF; 2.) benzene 2: 1.) 25percent KOH; 2.) m-chloroperoxybenzoic acid / 1.) MeOH; 2.) CH2Cl2 3: 80 percent / sodium borohydride / methanol / Heating View Scheme |
coptisine
(6R,7S)-8-Methyl-7-(6-vinyl-benzo[1,3]dioxol-5-yl)-6,7,8,9-tetrahydro-[1,3]dioxolo[4,5-h]isoquinolin-6-ol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.) LiAlH4 / 1.) THF; 2.) benzene 2: 1.) 25percent KOH; 2.) m-chloroperoxybenzoic acid / 1.) MeOH; 2.) CH2Cl2 3: 15 percent / sodium borohydride / methanol / Heating View Scheme |
coptisine
7,8,6',8'-tetrahydro-6H-(7'rN)-spiro[[1,3]dioxolo[4,5-g]isoquinoline-5,7'-indeno[4,5-d][1,3]dioxole]-6't,8'c-diol
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 2: 64 percent / LiAlH(OtBu)3 / tetrahydrofuran; diethyl ether / Heating 3: 67 percent / Heating 4: 74 percent / aq. KOH; dioxane / 48 h / Heating View Scheme |
coptisine
(+/-)-ochrobirine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 2: 61 percent 3: 89 percent / AgOAc 4: LiAlH4 View Scheme | |
Multi-step reaction with 5 steps 2: 64 percent / LiAlH(OtBu)3 / tetrahydrofuran; diethyl ether / Heating 3: 67 percent / Heating 4: 74 percent / aq. KOH; dioxane / 48 h / Heating 5: 73 percent / tetrahydrofuran / Ambient temperature View Scheme |
coptisine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 2: 61 percent 3: 89 percent / AgOAc View Scheme |
coptisine
C20H15NO7
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 2: 64 percent / LiAlH(OtBu)3 / tetrahydrofuran; diethyl ether / Heating 3: 67 percent / Heating View Scheme |
coptisine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 2: 61 percent View Scheme |
coptisine
C19H15NO5
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 2: 20 percent / LiAlH(OtBu)3 / tetrahydrofuran; diethyl ether / Heating View Scheme |
coptisine
C19H15NO5
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 2: 64 percent / LiAlH(OtBu)3 / tetrahydrofuran; diethyl ether / Heating View Scheme |
coptisine
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 2: 61 percent 3: 89 percent / AgOAc 4: LiAlH4 View Scheme |
coptisine
13-nitro-8-oxocoptisine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium hydroxide / 8 h / 80 °C 2: nitric acid / dichloromethane / 0.5 h / 20 - 30 °C / Reflux; Inert atmosphere View Scheme |
coptisine
12,13-dinitro-8-oxocoptisine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium hydroxide / 8 h / 80 °C 2: nitric acid / dichloromethane / 20 °C / Inert atmosphere View Scheme |
coptisine
1,2-methylenedioxy-9,10-dihydroxyl-12-sulfonyl-8-oxoprotoberberine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium hydroxide / 8 h / 80 °C 2: sulfuryl dichloride / dichloromethane / 2 h / 0 °C / Inert atmosphere View Scheme |
coptisine
8-thiocoptisine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium hydroxide / 8 h / 80 °C 2: tetraphosphorus decasulfide / pyridine; dichloromethane / 3 h / Reflux; Inert atmosphere View Scheme |
coptisine
13-bromo-8-thiocoptisine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: potassium hydroxide / 8 h / 80 °C 2: N-Bromosuccinimide / chloroform / 24 h / 20 °C / Reflux; Inert atmosphere 3: tetraphosphorus decasulfide / pyridine; dichloromethane / 3 h / Reflux; Inert atmosphere View Scheme |
coptisine
13-nitro-8-thiocoptisine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: potassium hydroxide / 8 h / 80 °C 2: nitric acid / dichloromethane / 0.5 h / 20 - 30 °C / Reflux; Inert atmosphere 3: tetraphosphorus decasulfide / pyridine; dichloromethane / 3 h / Reflux; Inert atmosphere View Scheme |
coptisine
12,13-dinitro-8-thiocoptisine
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: potassium hydroxide / 8 h / 80 °C 2: nitric acid / dichloromethane / 20 °C / Inert atmosphere 3: tetraphosphorus decasulfide / pyridine; dichloromethane / 3 h / Reflux; Inert atmosphere View Scheme |
coptisine
13-bromo-8-oxocoptisine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: potassium hydroxide / 8 h / 80 °C 2: N-Bromosuccinimide / chloroform / 24 h / 20 °C / Reflux; Inert atmosphere View Scheme |
coptisine
coptisinone
Conditions | Yield |
---|---|
With potassium hydroxide at 80℃; for 8h; | 28 mg |
With sodium hydroxide; potassium hexacyanoferrate(III) In water Reflux; |
Conditions | Yield |
---|---|
With potassium hydroxide at 80℃; for 8h; Inert atmosphere; | 39 mg |
Conditions | Yield |
---|---|
at 80℃; for 8h; Inert atmosphere; | 36 mg |
coptisine
1,2-dichloro-ethane
2,3-ethylenedioxy-9,10-ethylenedioxy-8-oxoprotoberbeirine
Conditions | Yield |
---|---|
With potassium hydroxide In dimethyl sulfoxide at 80℃; for 8h; Inert atmosphere; | 33 mg |
Product Name: Coptisine
Synonyms of Coptisine (CAS NO.3486-66-6) : [1,3]Benzodioxolo[5,6-a]-1,3-benzodioxolo[4,5-g]quinolizinium, 6,7-dihydro- ; 6,7-Dihydro[1,3]dioxolo[4,5-g][1,3]dioxolo[7,8]isoquino[3,2-a]isoquinoléin-5-ium ; Bis[methylenedioxy]protoberberine ; 6H,7H-[1,3]dioxolo[5,4-g][1,3]dioxolo[5'',4'':7,8]isoquino[3,2-a]isoquinolin-5-ium
Product Categories: Alkaloids
CAS NO: 3486-66-6
Molecular Formula:C19H14NO4
Molecular Weight :320.3182
Molecular Structure :
Coptisine is an alkaloid found in Chinese goldthread (Coptis chinensis). Famous for the bitter taste that it produces, Also found in Greater Celandine and has also been detected in Opium.
Coptisine (CAS NO.3486-66-6) is used in Chinese herbal medicine along with the related compound berberine for treating digestive disorders caused by bacterial infections.
1. | orl-rat TDLo:0.1 mg/kg | BIPBU* Biological & pharmaceutical bulletin. 24 (2001),1277. |
A poison by ingestion. When Coptisine (CAS NO.3486-66-6) is heated to decomposition it emits toxic vapors of NOx.
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