ELYMOCLAVINE supplier | CasNO.548-43-6

Name
elymoclavine
EINECS
CAS No. 548-43-6
Article Data9
CAS DataBase
Density 1.247g/cm³
Solubility
Melting Point 251°C (rough estimate)
Formula C16H18 N2 O
Boiling Point 468°Cat760mmHg
Molecular Weight 254.332
Flash Point 236.8°C
Transport Information
Appearance
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).
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Elymoclavine(6CI); D-8,9-Didehydro-6-methylergoline-8-methanol; Elymoclavin; NSC 109431
PSA 39.26000
LogP 1.97820

Synthetic route

: 1027016-28-9
(6aR,10aR)-9-(tert-Butyl-dimethyl-silanyloxymethyl)-7-methyl-4,6,6a,7,8,10a-hexahydro-indolo[4,3-fg]quinoline

: 548-43-6
elymoclavine

Conditions

Conditions	Yield
With pyridinium p-toluenesulfonate In ethanol at 20℃; for 48h;	95%

: 548-42-5
agroclavine

: 548-43-6
elymoclavine

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

: 487-89-8
Indole-3-carboxaldehyde

: 548-43-6
elymoclavine

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

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

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

: (E)-tert-butyl 3-formyl-4-(3-methoxy-3-oxoprop-1-en-1-yl)-1H-indole-1-carboxylate

: 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

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

: C19H20N2O6

: 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

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

: C18H22N2O5

: 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

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

: C20H24N2O6

: 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

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

: C18H20N2O4

: 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

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

: C30H44N2O5Si

: 548-43-6
elymoclavine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 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 2: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux 3: pyridinium p-toluenesulfonate / ethanol / 48 h / 20 °C View Scheme

: C18H20N2O5

: 548-43-6
elymoclavine

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1: sodium tetrahydroborate / tetrahydrofuran; methanol / 1 h / 20 °C 2: triethylamine / dichloromethane / 1 h / 0 - 20 °C 3: potassium carbonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); palladium diacetate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere 4: hydrogenchloride; zinc / methanol; water / 1 h 5: potassium carbonate / dichloromethane / 20 h / 20 °C 6: triethylamine / dichloromethane / 24 h / 20 °C 7: 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 8: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux 9: pyridinium p-toluenesulfonate / ethanol / 48 h / 20 °C View Scheme

Yield

Multi-step reaction with 9 steps
1: sodium tetrahydroborate / tetrahydrofuran; methanol / 1 h / 20 °C
2: triethylamine / dichloromethane / 1 h / 0 - 20 °C
3: potassium carbonate; (S)-(1,1'-binaphthalene)-2,2'-diylbis(diphenylphosphine); palladium diacetate / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere
4: hydrogenchloride; zinc / methanol; water / 1 h
5: potassium carbonate / dichloromethane / 20 h / 20 °C
6: triethylamine / dichloromethane / 24 h / 20 °C
7: 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
8: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux
9: pyridinium p-toluenesulfonate / ethanol / 48 h / 20 °C
View Scheme

: C18H22N2O2

: 548-43-6
elymoclavine

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: potassium carbonate / dichloromethane / 20 h / 20 °C 2: triethylamine / dichloromethane / 24 h / 20 °C 3: 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 4: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux 5: pyridinium p-toluenesulfonate / ethanol / 48 h / 20 °C View Scheme

Yield

Multi-step reaction with 5 steps
1: potassium carbonate / dichloromethane / 20 h / 20 °C
2: triethylamine / dichloromethane / 24 h / 20 °C
3: 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
4: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux
5: pyridinium p-toluenesulfonate / ethanol / 48 h / 20 °C
View Scheme

: C28H42N2O3Si

: 548-43-6
elymoclavine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / 24 h / 20 °C 2: 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 3: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux 4: pyridinium p-toluenesulfonate / ethanol / 48 h / 20 °C View Scheme

Yield

Multi-step reaction with 4 steps
1: triethylamine / dichloromethane / 24 h / 20 °C
2: 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
3: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / Reflux
4: pyridinium p-toluenesulfonate / ethanol / 48 h / 20 °C
View Scheme

: 548-43-6
elymoclavine

: 108-24-7
acetic anhydride

: 5080-45-5
8-acetoxymethyl-6-methyl-8,9-didehydro-ergoline

Conditions

Conditions	Yield
In pyridine Ambient temperature;	90%
In pyridine Ambient temperature; Yield given;

: 548-43-6
elymoclavine

: 18051-16-6
9,10-dihydrolysergol

Conditions

Conditions	Yield
With methanol; nickel In 1,4-dioxane Heating;	86%

: 548-43-6
elymoclavine

: 618-46-2
m-Chlorobenzoyl chloride

: 85893-06-7
O-3-Chlorobenzoyl-elymoclavin-hydrochlorid

Conditions

Conditions	Yield
With pyridine Ambient temperature;	77%

: 548-43-6
elymoclavine

: 122-01-0
4-chloro-benzoyl chloride

: 85893-07-8
O-4-Chlorobenzoyl-elymoclavin-hydrochlorid

Conditions

Conditions	Yield
With pyridine Ambient temperature;	69%

: 548-43-6
elymoclavine

: 100-07-2
4-methoxy-benzoyl chloride

: 85893-09-0
O-4-Methoxybenzoyl-elymoclavin-hydrochlorid

Conditions

Conditions	Yield
With pyridine at 70℃;	63%

: 548-43-6
elymoclavine

: 4521-61-3
3,4,5-Trimethoxybenzoyl chloride

: 85893-10-3
O-3,4,5-Trimethoxybenzoyl-elymoclavin-hydrochlorid

Conditions

Conditions	Yield
With pyridine at 100℃;	62%

: 548-43-6
elymoclavine

: 874-60-2
4-methyl-benzoyl chloride

: 85893-08-9
O-4-Methylbenzoyl-elymoclavin-hydrochlorid

Conditions

Conditions	Yield
With pyridine at 70℃;	62%

: 548-43-6
elymoclavine

: 73621-60-0
N-((4aR,10bR)-2-Hydroxymethyl-4-methyl-6-oxo-3,4,4a,5,6,10b-hexahydro-benzo[f]quinolin-7-yl)-formamide

Conditions

Conditions	Yield
With sodium periodate; methanesulfonic acid In methanol at 25℃; for 2.75h;	50%

: 548-43-6
elymoclavine

: 604-69-3
β-D-glucose pentaacetate

: 180144-99-4
Acetic acid (2R,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((6aR,10aR)-7-methyl-4,6,6a,7,8,10a-hexahydro-indolo[4,3-fg]quinolin-9-ylmethoxy)-tetrahydro-pyran-3-yl ester

Conditions

Conditions	Yield
With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve In nitromethane; dichloromethane for 3h; Ambient temperature;	46%

: 548-43-6
elymoclavine

: 3150-24-1
4-nitrophenyl-β-D-galactopyranoside

A: 145603-56-1
elymoclavine-β-D-galactoside

B: 145603-59-4
GAL-β(1-6)-GAL-β-O-elymoclavine

Conditions

Conditions	Yield
In various solvent(s) at 24℃; for 3h; β-galactosidase from Aspergillus orizae or from Escherichia coli; other ergot alkaloids;	A 37% B n/a
With 2-hydroxyethanethiol; citric acid; magnesium chloride at 24℃; for 3h; β-galactosidase from Aspergillus oryzae, K-Pi-buffer;	A 37% B n/a
With 2-hydroxyethanethiol; citric acid; magnesium chloride at 24℃; β-galactosidase from Aspergillus oryzae, K-Pi buffer;	A n/a B 1%

...Expand

: 548-43-6
elymoclavine

: 57-50-1
Sucrose

: (2R,3S,4S,5R)-2,5-Bis-hydroxymethyl-2-((6aR,10aR)-7-methyl-4,6,6a,7,8,10a-hexahydro-indolo[4,3-fg]quinolin-9-ylmethoxy)-tetrahydro-furan-3,4-diol

Conditions

Conditions	Yield
With succinic acid; DL-5-fluorotryptophan In water at 24℃; for 1296h; Claviceps purpurea 88-EP-47;	24%

: 548-43-6
elymoclavine

: 7493-95-0
4-nitrophenyl α-D-galactoside

A: (2R,3R,4S,5R,6R)-2-[(2R,3S,4S,5R,6S)-3,5-Dihydroxy-2-hydroxymethyl-6-((6aR,10aR)-7-methyl-4,6,6a,7,8,10a-hexahydro-indolo[4,3-fg]quinolin-9-ylmethoxy)-tetrahydro-pyran-4-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

B: (2R,3R,4S,5R,6S)-2-Hydroxymethyl-6-((6aR,10aR)-7-methyl-4,6,6a,7,8,10a-hexahydro-indolo[4,3-fg]quinolin-9-ylmethoxy)-tetrahydro-pyran-3,4,5-triol

Conditions

Conditions	Yield
With α-galactosidase form A. oryzae; citric acid at 30℃; pH 5;	A 3% B 23%

...Expand

: 548-43-6
elymoclavine

: 74-88-4
methyl iodide

: 1935-35-9
1-Methylelymoclavin

Conditions

Conditions	Yield
With potassium amide; ferric nitrate In diethyl ether; ammonia at -50 - -40℃; for 0.5h;	14%

: 548-43-6
elymoclavine

: 10357-27-4
4-nitrophenyl-α-D-mannopyranoside

: (2R,3S,4S,5S,6S)-2-Hydroxymethyl-6-((6aR,10aR)-7-methyl-4,6,6a,7,8,10a-hexahydro-indolo[4,3-fg]quinolin-9-ylmethoxy)-tetrahydro-pyran-3,4,5-triol

Conditions

Conditions	Yield
With α-mannosidase (almond); citric acid at 30℃; pH 5;	3%

: 548-43-6
elymoclavine

: 478-91-1
Lysergen

Conditions

Conditions	Yield
With sodium; butan-1-ol

: 548-43-6
elymoclavine

: 548-42-5
agroclavine

Conditions

Conditions	Yield
With sodium; butan-1-ol

: 548-43-6
elymoclavine

: 436-41-9, 478-89-7, 569-26-6, 40759-95-3, 61425-10-3, 74644-94-3, 74644-95-4, 74644-96-5
(+)-Costaclavine

Conditions

Conditions	Yield
With sodium; butan-1-ol
Multi-step reaction with 2 steps 1: sodium; butan-1-ol 2: sodium; butan-1-ol View Scheme

: 548-43-6
elymoclavine

: 18162-48-6
tert-butyldimethylsilyl chloride

: 1027016-28-9
(6aR,10aR)-9-(tert-Butyl-dimethyl-silanyloxymethyl)-7-methyl-4,6,6a,7,8,10a-hexahydro-indolo[4,3-fg]quinoline

Conditions

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide for 1h; Ambient temperature;

: 548-43-6
elymoclavine

: 56862-50-1
8-chloromethyl-6-methyl-8,9-didehydro-ergoline

Conditions

Conditions	Yield
With trichlorophosphate for 1.5h; Heating;
With oxalyl dichloride In N,N-dimethyl-formamide; acetonitrile at -70℃;

: 548-43-6
elymoclavine

A: ((6aR,7R,10aR)-7-Methyl-7-oxy-4,6,6a,7,8,10a-hexahydro-indolo[4,3-fg]quinolin-9-yl)-methanol

B: ((6aR,7S,10aR)-7-Methyl-7-oxy-4,6,6a,7,8,10a-hexahydro-indolo[4,3-fg]quinolin-9-yl)-methanol

Conditions

Conditions	Yield
With dihydrogen peroxide In isopropyl alcohol at 60℃; for 2h; Yield given. Yields of byproduct given;

: 4524-93-0
Cyclopentanecarboxylic acid chloride

: 548-43-6
elymoclavine

: Cyclopentanecarboxylic acid (6aR,10aR)-7-methyl-4,6,6a,7,8,10a-hexahydro-indolo[4,3-fg]quinolin-9-ylmethyl ester

Conditions

Conditions	Yield
With pyridine; dmap for 12h; Ambient temperature;

: 2307-69-9
toluene-4-sulfonic acid isopropyl ester

: 548-43-6
elymoclavine

: 1-isopropylelymoclavine

Conditions

Conditions	Yield
With potassium hydroxide; 18-crown-6 ether In dimethyl sulfoxide for 1h;

: 6557-86-4
cycloheptanecarbonyl chloride

: 548-43-6
elymoclavine

: Cycloheptanecarboxylic acid (6aR,10aR)-7-methyl-4,6,6a,7,8,10a-hexahydro-indolo[4,3-fg]quinolin-9-ylmethyl ester

Conditions

Conditions	Yield
With pyridine; dmap for 12h; Ambient temperature;

: 548-43-6
elymoclavine

: 2719-27-9
cyclohexanylcarbonyl chloride

: Cyclohexanecarboxylic acid (6aR,10aR)-7-methyl-4,6,6a,7,8,10a-hexahydro-indolo[4,3-fg]quinolin-9-ylmethyl ester

Conditions

Conditions	Yield
With pyridine; dmap for 12h; Ambient temperature;

: 548-43-6
elymoclavine

: 4-methoxy-cyclohexanecarbonyl chloride

: 4-Methoxy-cyclohexanecarboxylic acid (6aR,10aR)-7-methyl-4,6,6a,7,8,10a-hexahydro-indolo[4,3-fg]quinolin-9-ylmethyl ester

Conditions

Conditions	Yield
With pyridine; dmap for 12h; Ambient temperature;

: 548-43-6
elymoclavine

: 5006-22-4
Cyclobutanecarbonyl chloride

: Cyclobutanecarboxylic acid (6aR,10aR)-7-methyl-4,6,6a,7,8,10a-hexahydro-indolo[4,3-fg]quinolin-9-ylmethyl ester

Conditions

Conditions	Yield
With pyridine; dmap for 12h; Ambient temperature;

ELYMOCLAVINE Chemical Properties

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

ELYMOCLAVINE 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. ).

ELYMOCLAVINE 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.

ELYMOCLAVINE Production

Ergot alkaloid isolated from cultures of fungi parasitic on Elymis mollis Trin; toxic alkaloid produced by Claviceps purpurea

ELYMOCLAVINE 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.

Product Name

elymoclavine

Synthetic route

ELYMOCLAVINE Chemical Properties

ELYMOCLAVINE History

ELYMOCLAVINE Uses

ELYMOCLAVINE Production

ELYMOCLAVINE Safety Profile

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