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Basic Information
| CAS No.: | 517-66-8 |
|---|---|
| Name: | Dicentrin |
| Molecular Structure: | |
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|
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| Formula: | C20H21 N O4 |
| Molecular Weight: | 339.391 |
| Synonyms: | 5H-Benzo[g]-1,3-benzodioxolo[6,5,4-de]quinoline,6,7,7a,8-tetrahydro-10,11-dimethoxy-7-methyl-, (S)-; 6aa-Aporphine,9,10-dimethoxy-1,2-(methylenedioxy)- (8CI); Dicentrine (6CI,7CI);(+)-Dicentrine; 1,2-(Methylenedioxy)-9,10-dimethoxy-6aa-aporphine;9,10-Dimethoxy-1,2-(methylenedioxy)-6aa-aporphine; Eximine; O,N-Dimethyllitseferine;d-Dicentrine |
| Density: | 1.266g/cm3 |
| Melting Point: | 177-178℃ |
| Boiling Point: | 480.7°Cat760mmHg |
| Flash Point: | 142.7°C |
| Safety: | Mutation data reported. When heated to decomposition it emits toxic vapors of NOx. |
| PSA: | 40.16000 |
| LogP: | 3.12250 |
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Synthetic route
- 517-66-8
(S)-dicentrine
Conditions
| Conditions | Yield |
|---|---|
| With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; Inert atmosphere; | 53% |
| With lithium aluminium tetrahydride In diethyl ether at 0℃; |
Conditions
| Conditions | Yield |
|---|---|
| (i) HCO2H, (ii) /BRN= 102415/, MeOH, Et2O; Multistep reaction; |
...Expand
- 72203-90-8
(7aS)-10,11-dimethoxy-7-methyl-6,7,7a,8-tetrahydro-5H-benzo[g][1,3]dioxolo[4',5':4,5]benzo[1,2,3-de]quinolin-5c-ol; hydrochloride
- 517-66-8
(S)-dicentrine
Conditions
| Conditions | Yield |
|---|---|
| With hydrogenchloride; palladium on activated charcoal In acetic acid at 50 - 60℃; under 3102.9 Torr; for 4h; |
- 517-66-8
(S)-dicentrine
Conditions
| Conditions | Yield |
|---|---|
| With D-tartaric acid; L-Tartaric acid |
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: diethyl ether; methanol View Scheme |
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 6 steps 1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 4-methyl-morpholine / N,N-dimethyl-formamide / 4 h / 0 - 20 °C / Inert atmosphere 2: trifluoromethylsulfonic anhydride; 2-chloropyridine / dichloromethane / 0.25 h / -78 - 0 °C / Inert atmosphere 3: triethylamine; formic acid; Noyori's catalyst / N,N-dimethyl-formamide / 24 h / 0 - 20 °C / Inert atmosphere 4: N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 10 h / 20 °C / Inert atmosphere 5: palladium diacetate; potassium carbonate; di-tert-butyl(methyl)phosphonium tetrafluoroborate salt / N,N-dimethyl acetamide / 8 h / 130 °C / Inert atmosphere 6: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere View Scheme |
- 25829-00-9
N-(2-(benzo[d] [1,3]dioxol-5-yl)ethyl)-2-(2-bromo-4,5-dimethoxyphenyl)acetamide
- 517-66-8
(S)-dicentrine
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 5 steps 1: trifluoromethylsulfonic anhydride; 2-chloropyridine / dichloromethane / 0.25 h / -78 - 0 °C / Inert atmosphere 2: triethylamine; formic acid; Noyori's catalyst / N,N-dimethyl-formamide / 24 h / 0 - 20 °C / Inert atmosphere 3: N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 10 h / 20 °C / Inert atmosphere 4: palladium diacetate; potassium carbonate; di-tert-butyl(methyl)phosphonium tetrafluoroborate salt / N,N-dimethyl acetamide / 8 h / 130 °C / Inert atmosphere 5: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere View Scheme |
- 517-66-8
(S)-dicentrine
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 10 h / 20 °C / Inert atmosphere 2: palladium diacetate; potassium carbonate; di-tert-butyl(methyl)phosphonium tetrafluoroborate salt / N,N-dimethyl acetamide / 8 h / 130 °C / Inert atmosphere 3: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere View Scheme |
- 80041-80-1
5-(2-bromo-4,5-dimethoxy-benzyl)-7,8-dihydro-[1,3]dioxolo[4,5-g]isoquinoline
- 517-66-8
(S)-dicentrine
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 4 steps 1: triethylamine; formic acid; Noyori's catalyst / N,N-dimethyl-formamide / 24 h / 0 - 20 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; dmap / dichloromethane / 10 h / 20 °C / Inert atmosphere 3: palladium diacetate; potassium carbonate; di-tert-butyl(methyl)phosphonium tetrafluoroborate salt / N,N-dimethyl acetamide / 8 h / 130 °C / Inert atmosphere 4: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere View Scheme |
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Dicentrin
Toxicity Data With Reference
| 1. | mic-sat 20 µLg/plate | MUREAV Mutation Research. 240 (1990),267. |
Safety Profile
Mutation data reported. When heated to decomposition it emits toxic vapors of NOx.