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Basic Information
| CAS No.: | 548-43-6 |
|---|---|
| Name: | elymoclavine |
| Article Data: | 9 |
| Molecular Structure: | |
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| Formula: | C16H18 N2 O |
| Molecular Weight: | 254.332 |
| Synonyms: | Elymoclavine(6CI); D-8,9-Didehydro-6-methylergoline-8-methanol; Elymoclavin; NSC 109431 |
| Density: | 1.247g/cm3 |
| Melting Point: | 251°C (rough estimate) |
| Boiling Point: | 468°Cat760mmHg |
| Flash Point: | 236.8°C |
| Safety: | A poison by intraperitoneal and intravenous routes. Experimental teratogenic and reproductive effects. When heated to decomposition it emits acrid smoke and fumes. See also N,N-DIETHYLLYSERGAMIDE (LSD). |
| PSA: | 39.26000 |
| LogP: | 1.97820 |
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- 548-43-6
elymoclavine
Conditions
| Conditions | Yield |
|---|---|
| With pyridinium p-toluenesulfonate In ethanol at 20℃; for 48h; | 95% |
Conditions
| Conditions | Yield |
|---|---|
| for 168h; fermentative bioconversion by Ca-alginate immibilized cells of submerged cultures of C. fusiformis W1; | 90% |
- 63-68-3
L-methionine
- 150-97-0, 690-72-2, 17817-88-8, 32451-23-3
D,L-mevalonic acid
- 54-12-6
Trp
- 548-43-6
elymoclavine
Conditions
| Conditions | Yield |
|---|---|
| With phosphate buffer pH 7.3 In water for 48h; Claviceps sp., strain SD58, medium NL 406; |
...Expand
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 13 steps 1: dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver hexafluoroantimonate; copper diacetate / 4 h / 110 °C / Inert atmosphere 2: dmap / acetonitrile / 0.5 h / 40 °C 3: ammonium acetate / 2 h / 70 °C 4: diisobutylaluminium hydride / tetrahydrofuran; hexane / 1 h / -78 °C 5: sodium tetrahydroborate / tetrahydrofuran; methanol / 1 h / 20 °C 6: triethylamine / dichloromethane / 1 h / 0 - 20 °C 7: potassium carbonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); palladium diacetate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere 8: hydrogenchloride; zinc / methanol; water / 1 h 9: potassium carbonate / dichloromethane / 20 h / 20 °C 10: triethylamine / dichloromethane / 24 h / 20 °C 11: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride / toluene / 12 h / 80 °C / Inert atmosphere 12: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux 13: pyridinium p-toluenesulfonate / ethanol / 48 h / 20 °C View Scheme |
- 115698-38-9
(E)-methyl 3-(3-formyl-1H-indol-4-yl)acrylate
- 548-43-6
elymoclavine
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 12 steps 1: dmap / acetonitrile / 0.5 h / 40 °C 2: ammonium acetate / 2 h / 70 °C 3: diisobutylaluminium hydride / tetrahydrofuran; hexane / 1 h / -78 °C 4: sodium tetrahydroborate / tetrahydrofuran; methanol / 1 h / 20 °C 5: triethylamine / dichloromethane / 1 h / 0 - 20 °C 6: potassium carbonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); palladium diacetate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere 7: hydrogenchloride; zinc / methanol; water / 1 h 8: potassium carbonate / dichloromethane / 20 h / 20 °C 9: triethylamine / dichloromethane / 24 h / 20 °C 10: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride / toluene / 12 h / 80 °C / Inert atmosphere 11: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux 12: pyridinium p-toluenesulfonate / ethanol / 48 h / 20 °C View Scheme |
- 548-43-6
elymoclavine
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 11 steps 1: ammonium acetate / 2 h / 70 °C 2: diisobutylaluminium hydride / tetrahydrofuran; hexane / 1 h / -78 °C 3: sodium tetrahydroborate / tetrahydrofuran; methanol / 1 h / 20 °C 4: triethylamine / dichloromethane / 1 h / 0 - 20 °C 5: potassium carbonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); palladium diacetate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere 6: hydrogenchloride; zinc / methanol; water / 1 h 7: potassium carbonate / dichloromethane / 20 h / 20 °C 8: triethylamine / dichloromethane / 24 h / 20 °C 9: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride / toluene / 12 h / 80 °C / Inert atmosphere 10: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux 11: pyridinium p-toluenesulfonate / ethanol / 48 h / 20 °C View Scheme |
- 548-43-6
elymoclavine
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 10 steps 1: diisobutylaluminium hydride / tetrahydrofuran; hexane / 1 h / -78 °C 2: sodium tetrahydroborate / tetrahydrofuran; methanol / 1 h / 20 °C 3: triethylamine / dichloromethane / 1 h / 0 - 20 °C 4: potassium carbonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); palladium diacetate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere 5: hydrogenchloride; zinc / methanol; water / 1 h 6: potassium carbonate / dichloromethane / 20 h / 20 °C 7: triethylamine / dichloromethane / 24 h / 20 °C 8: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride / toluene / 12 h / 80 °C / Inert atmosphere 9: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux 10: pyridinium p-toluenesulfonate / ethanol / 48 h / 20 °C View Scheme |
- 548-43-6
elymoclavine
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 8 steps 1: triethylamine / dichloromethane / 1 h / 0 - 20 °C 2: potassium carbonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); palladium diacetate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere 3: hydrogenchloride; zinc / methanol; water / 1 h 4: potassium carbonate / dichloromethane / 20 h / 20 °C 5: triethylamine / dichloromethane / 24 h / 20 °C 6: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride / toluene / 12 h / 80 °C / Inert atmosphere 7: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux 8: pyridinium p-toluenesulfonate / ethanol / 48 h / 20 °C View Scheme |
- 548-43-6
elymoclavine
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 7 steps 1: potassium carbonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); palladium diacetate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere 2: hydrogenchloride; zinc / methanol; water / 1 h 3: potassium carbonate / dichloromethane / 20 h / 20 °C 4: triethylamine / dichloromethane / 24 h / 20 °C 5: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride / toluene / 12 h / 80 °C / Inert atmosphere 6: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux 7: pyridinium p-toluenesulfonate / ethanol / 48 h / 20 °C View Scheme |
- 548-43-6
elymoclavine
Conditions
| Conditions | Yield |
|---|---|
| Multi-step reaction with 6 steps 1: hydrogenchloride; zinc / methanol; water / 1 h 2: potassium carbonate / dichloromethane / 20 h / 20 °C 3: triethylamine / dichloromethane / 24 h / 20 °C 4: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride / toluene / 12 h / 80 °C / Inert atmosphere 5: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux 6: pyridinium p-toluenesulfonate / ethanol / 48 h / 20 °C View Scheme |
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elymoclavine
Chemistry
Molecular Formula:C16H18N2O
Molecular Weight:254.36
Density:1.247g/cm3
Boiling Point:468°C at 760mmHg
Flash Point:236.8°C
Properties:A solid
Mp: 250–252°C
Molecular Weight:254.36
Density:1.247g/cm3
Boiling Point:468°C at 760mmHg
Flash Point:236.8°C
Properties:A solid
Mp: 250–252°C
History
A close chemical relative of LSD found in ergot fungi and bindweeds of the genus Ipomoea, Fam. convolvulaceae ( JANSAG Journal of Animal Science. 41 (1975),1700. ).
Uses
Elymoclavine soluble in pyridine is sympathetic to stimulate the central role and the central nervous system stimulant. Ergot is by and bindweed Branch silver leaf and flower is a gland vine leaves (Stictocardia tiliaefolia) from the plant alkaloids.
Production
Ergot alkaloid isolated from cultures of fungi parasitic on Elymis mollis Trin; toxic alkaloid produced by Claviceps purpurea
Safety Profile
Elymoclavine may be a poison by intraperitoneal and intravenous routes. Experimental teratogenic and reproductive effects. When heated to decomposition it emits acrid smoke and fumes.