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inquiryFINETECH INDUSTRY LIMITED is a LONDON based CRO company providing drug discovery & development services to worldwide clients. FINETECH INDUSTRY LIMITED supplies the (S)-(+)-3,4,8,8A-TETRAHYDRO-8A-METHYL-1,6(2H,7H)-NAPHTHALENEDIONE, CAS:33878-99-8 wit
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inquiryDebyesci is here who supplied several kinds of chemical products to global pharmaceutical, drug discovery, agrochemical and biotechnology industries for four yearsOur key scientific leadership team has gained experience in top research and developmen
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inquiry(4aS,5S)-4,4a,5,6,7,8-hexahydro-5-hydroxy-4a-methylnaphthalen-2(3H)-one
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
Conditions | Yield |
---|---|
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 20℃; for 17h; enantioselective reaction; | 97.9% |
With jones reagent Oxidation; |
2-methyl-2-(3-oxobutyl)cyclohexane-1,3-dione
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
Conditions | Yield |
---|---|
With N-tosyl-(Sa)-1,1'-binaphthyl-2,2'-diamine-L-prolinamide; benzoic acid at 25℃; for 27h; Neat (no solvent); optical yield given as %ee; enantioselective reaction; | 95% |
With N-tosyl-(Sa)-1,1'-binaphthyl-2,2'-diamine-L-prolinamide; benzoic acid for 168h; optical yield given as %ee; enantioselective reaction; | 94% |
With L-proline at 20℃; for 2h; Catalytic behavior; Aldol Condensation; Ionic liquid; enantioselective reaction; | 88% |
14-noreudesma-4,11-dien-3,9-dione
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
Conditions | Yield |
---|---|
Stage #1: 14-noreudesma-4,11-dien-3,9-dione With methanol; ozone Stage #2: With ferrous(II) sulfate heptahydrate; thiophenol at -78 - 20℃; for 0.5h; | 91% |
2-methyl-2-(3-oxobutyl)cyclohexane-1,3-dione
A
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
B
(R)-Wieland-Miescher ketone
Conditions | Yield |
---|---|
With L-proline at 20℃; for 2h; Catalytic behavior; Temperature; Solvent; Reagent/catalyst; Aldol Condensation; Ionic liquid; enantioselective reaction; | A 78% B n/a |
With (S)-2-(1-pyrrolidinylmethyl)pyrrolidine In dimethyl sulfoxide at 20℃; for 10h; Hajos-Parrish-Eder-Sauer-Wiechert reaction; optical yield given as %ee; enantioselective reaction; | A 55% B n/a |
With (S)-2-(1-pyrrolidinylmethyl)pyrrolidine; trifluoroacetic acid In dimethyl sulfoxide at 20℃; for 48h; Hajos-Parrish-Eder-Sauer-Wiechert reaction; optical yield given as %ee; enantioselective reaction; | A n/a B 52% |
2-methyl-2-(3-oxobutyl)cyclohexane-1,3-dione
A
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
B
Wieland-Miescher ketone
Conditions | Yield |
---|---|
L-proline In N,N-dimethyl-formamide for 168h; Ambient temperature; | A 36% B 42% |
Wieland-Miescher ketone
B
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
C
(R)-Wieland-Miescher ketone
D
(-)-(4aR,5S)-5-hydroxy-4a-methyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one
Conditions | Yield |
---|---|
With α-D-glucose 6-phosphate; oxygen; NADP; glucose-6-phosphate dehydrogenase; recombinant c-hexanone monooxygenase (E. coli TOP10 pQR239) In phosphate buffer at 20℃; for 26h; pH=8.7; Baeyer-Villiger oxidation; Further byproducts given; | A 35% B n/a C n/a D n/a |
2-methyl-2-(3-oxobutyl)cyclohexane-1,3-dione
A
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
Conditions | Yield |
---|---|
With antibody 38C2; PBS buffer In 1,2-dimethoxyethane for 504h; Ambient temperature; Yields of byproduct given. Title compound not separated from byproducts; | A n/a B 7% C n/a |
2-methyl-2-(3-oxobutyl)cyclohexane-1,3-dione
A
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
B
6-hydroxy-1,6-dimethylbicyclo<3.3.1>nonane-2,9-dione
C
(R)-Wieland-Miescher ketone
Conditions | Yield |
---|---|
With L-proline In N,N-dimethyl-formamide for 24h; Ambient temperature; Yield given. Title compound not separated from byproducts; |
5β-hydroxy-5α-ethynyl-10β-methyl-Δ1(9)-octalin-2-one
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
Conditions | Yield |
---|---|
With silver carbonate In dimethyl sulfoxide |
Wieland-Miescher ketone
A
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
B
(-)-(4aR,5S)-5-hydroxy-4a-methyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one
Conditions | Yield |
---|---|
With D-glucose; yeast cells of Candida melibiosica IAM4488 In phosphate buffer at 30℃; for 68h; pH=6.5; Reduction; Enzymatic reaction; |
Wieland-Miescher ketone
A
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
B
(R)-Wieland-Miescher ketone
Conditions | Yield |
---|---|
Kinetic resolution; baker's yeast reduction; Title compound not separated from byproducts; | |
In hexane; isopropyl alcohol Reagent/catalyst; Resolution of racemate; |
2-methylcyclohexane-1,3-dione
methyl vinyl ketone
A
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
B
(R)-Wieland-Miescher ketone
Conditions | Yield |
---|---|
With L-proline In dimethyl sulfoxide at 35℃; for 89h; Product distribution; Further Variations:; Reagents; Addition; | |
With L-proline In dimethyl sulfoxide at 35℃; for 89h; Addition; Title compound not separated from byproducts; | |
Stage #1: 2-methylcyclohexane-1,3-dione With L-proline In dimethyl sulfoxide at 15 - 25℃; for 6h; Stage #2: methyl vinyl ketone In dimethyl sulfoxide at 15 - 25℃; for 180h; asymmetric Robinson annulation; Stage #3: With pyridinium p-toluenesulfonate In benzene for 2h; Heating; Title compound not separated from byproducts; |
2-methyl-2-(3-oxobutyl)cyclohexane-1,3-dione
C
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
Conditions | Yield |
---|---|
With water In acetonitrile Heating; Title compound not separated from byproducts.; |
2-methyl-2-(3-oxobutyl)cyclohexane-1,3-dione
C
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
Conditions | Yield |
---|---|
With water; 18O-labeled water In acetonitrile at 80℃; Title compound not separated from byproducts.; |
2-methylcyclohexane-1,3-dione
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: triethylamine / acetonitrile / 20 °C 2: (S)-5,6-dimethyl-2-(pyrrolidin-2-yl)-1H-benzimidazole; TFA / tetrahydrofuran / 48 h / 0 °C View Scheme | |
Multi-step reaction with 2 steps 1: (S)-2-diphenylmethyl-pirrolidine 2: L-proline / 120 h / 25 °C View Scheme | |
Multi-step reaction with 3 steps 1: H2O 2: (i) aq. HClO4, L-proline, MeCN, (ii) /BRN= 969178/, liq. NH3, Et2O 3: Ag2CO3 / dimethylsulfoxide View Scheme |
Wieland-Miescher ketone
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: yeast cells of Toluraspora delbrueckii IFO 10921; glucose / aq. phosphate buffer / 30 °C / pH 6.5 / Enzymatic reaction 2: Jones reagent View Scheme | |
Multi-step reaction with 2 steps 1: NADPH; glucose dehydrogenase; 7α-hydroxysteroid dehydrogenase from extremophilic bacterium Deinococcus marmoris strain / aq. phosphate buffer; dimethyl sulfoxide / 25 °C / Enzymatic reaction 2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 17 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: NADPH; glucose dehydrogenase; IS2-SDR from Icelandic hot spring sediments / aq. phosphate buffer; dimethyl sulfoxide / 25 °C / Enzymatic reaction 2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 17 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: sodium tetrahydroborate / ethanol / 4 h / 0 °C 2: Amano Lipase PS / acetone / 144 h / 45 °C / Enzymatic reaction 3: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 17 h / 20 °C View Scheme |
2-methyl-2-(3-oxobutyl)cyclohexane-1,3-dione
A
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
B
(R)-Wieland-Miescher ketone
C
cis-9-Hydroxy-10-methyl-dekalin-2,5-dion
Conditions | Yield |
---|---|
With (S)-N-(4-nitrophenyl)pyrrolidine-2-carboxamide In chloroform at 20℃; Hajos-Parrish reaction; optical yield given as %ee; enantioselective reaction; |
2-methyl-2-(3-oxobutyl)cyclohexane-1,3-dione
A
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
B
cis-9-Hydroxy-10-methyl-dekalin-2,5-dion
Conditions | Yield |
---|---|
With (S)-N-(3,5-bis(trifluoromethyl)phenyl)pyrrolidine-2-carboxamide In chloroform at 20℃; Hajos-Parrish reaction; optical yield given as %ee; enantioselective reaction; | |
With formic acid; (S)-N-{3,6-dichloro-8-[N-(2,4,4-trimethylpentan-2-yl)sulfamoyl]-9H-carbazol-1-yl}pyrrolidine-2-carboxamide formate In chloroform-d1 at 20℃; for 130h; enantioselective reaction; | A n/a B n/a |
2-methylcyclohexane-1,3-dione
methyl vinyl ketone
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
Conditions | Yield |
---|---|
With L-proline Robinson annulation; |
2-methyl-2-(3-oxobutyl)cyclohexane-1,3-dione
cyclohexanone
A
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
B
(R)-Wieland-Miescher ketone
Conditions | Yield |
---|---|
With 4-nitro-benzoic acid In water at 22℃; for 24h; Aldol condensation; optical yield given as %ee; enantioselective reaction; |
2-methylcyclohexane-1,3-dione
A
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
B
(R)-Wieland-Miescher ketone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: triethylamine / 3 h / Inert atmosphere 2: benzoic acid / neat (no solvent) / 120 h / 25 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 12 h 2: acetic acid / water / 120 h / 0 °C View Scheme | |
Multi-step reaction with 2 steps 1: acetic acid; hydroquinone / water / 80 °C 2: L-proline / dimethyl sulfoxide / 120 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: lipase AS / acetone; dimethyl sulfoxide / 192 h / 10 °C / Inert atmosphere; Enzymatic reaction 2: toluene-4-sulfonic acid / acetone; dimethyl sulfoxide / 2 h / 10 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1: triethylamine / neat (no solvent) / 16 h / 20 °C 2: (R)-pyrrolidine-2-(N-(3,5-bis(trifluoromethyl)phenyl)carboxamide) / chloroform / 168 h / 20 °C / Inert atmosphere View Scheme |
cis-9-Hydroxy-10-methyl-dekalin-2,5-dion
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
Conditions | Yield |
---|---|
In diethyl ether at -20℃; | 101.2 g |
(±)-4a,5-cis-(5-hydroxy-4a-methyl-4,4 a,5,6,7,8-hexahydronaphthalen-2(3H)-one)
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Amano Lipase PS / acetone / 144 h / 45 °C / Enzymatic reaction 2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 17 h / 20 °C View Scheme |
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
(4aS,5S)-4,4a,5,6,7,8-hexahydro-5-hydroxy-4a-methylnaphthalen-2(3H)-one
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol; dichloromethane at -78℃; for 0.25h; chemoselective reaction; | 100% |
With sodium tetrahydroborate In methanol at 0℃; for 0.5h; | 97% |
With sodium tetrahydroborate In ethanol at 0℃; | 97% |
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
ethane-1,2-dithiol
(S)-7a′-methyl-2′,3′,7′,7a′-tetrahydrospiro[[1,3]dithiolane-2,5′-inden]-1′(6′H)-one
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In acetic acid for 5h; Ambient temperature; | 99% |
With toluene-4-sulfonic acid In acetic acid for 6h; | 93% |
With toluene-4-sulfonic acid In acetic acid for 5h; Ambient temperature; | 92% |
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
(1S,6R)-1-methylbicyclo[4.4.0]decane-2,8-dione
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In hydrogenchloride; ethanol | 98% |
With glucose-6-phosphate dehydrogenase; metagenomic ene-reductase from pQR1907; β-D-glucose-6-phosphate sodium salt; NADPH In dimethyl sulfoxide at 30℃; for 20h; pH=7.4; Reagent/catalyst; Enzymatic reaction; stereoselective reaction; | 95% |
Multi-step reaction with 2 steps 1.1: 5%-palladium/activated carbon; palladium dichloride; hydrogen / 0.25 h / 20 °C 1.2: 48 h / 20 °C 2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide / 20 h / 70 °C View Scheme | |
With palladium on activated carbon; hydrogen In ethyl acetate at 20℃; for 2h; |
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
ethylene glycol
(8aS)-1,1-(1,2-ethylenedioxy)-1,2,3,4,6,7,8,8a-octahydro-8a-methyl-6-oxonaphthalene
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene for 0.916667h; Heating; | 96.7% |
In toluene for 5h; Heating; | 95% |
With 4 A molecular sieve; toluene-4-sulfonic acid at 20℃; for 0.383333h; | 93% |
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
methyllithium
cis-4a,8a-dimethyloctahydro-2(1H),5(6H)-dione
Conditions | Yield |
---|---|
With copper(l) iodide In diethyl ether at 0 - 20℃; | 96% |
2-ethyl-2-methyl-1,3-dioxolane
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
(8aS)-1,1-(1,2-ethylenedioxy)-1,2,3,4,6,7,8,8a-octahydro-8a-methyl-6-oxonaphthalene
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In ethylene glycol Inert atmosphere; regioselective reaction; | 95% |
With toluene-4-sulfonic acid; ethylene glycol | 94% |
With toluene-4-sulfonic acid In ethylene glycol for 30h; Ambient temperature; | 79% |
With toluene-4-sulfonic acid | |
With toluene-4-sulfonic acid In ethylene glycol |
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
ethylene glycol
(S)-4a-methyl-4,4a,6,7-tetrahydro-1H-spiro[naphthalene-2,2'-[1,3]dioxolan]-5(3H)-one
Conditions | Yield |
---|---|
With 2,4,6-collidinium p-toluenesulfonate Inert atmosphere; Reflux; | 93% |
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
trifluoromethylsulfonic anhydride
Conditions | Yield |
---|---|
With 2,6-di-tert-butyl-4-methylpyridine In dichloromethane at 0 - 20℃; for 1h; | 88% |
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
Conditions | Yield |
---|---|
With hydrogen; <((t-Bu)2PH)PdP(t-Bu)2>2 saturated with oxygen In tetrahydrofuran under 760 Torr; for 12h; Ambient temperature; | 83% |
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
(R)-1,2,3,4,8,8a-hexahydro-1β-hydroxy-8aβ-methyl-6-(7H)-naphthalenone
Conditions | Yield |
---|---|
Stage #1: (S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione With sodium tetrahydroborate In ethanol at 0℃; for 3.5h; Stage #2: With acetic acid In ethanol | 81% |
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
acetic anhydride
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene at 115℃; for 5.5h; Inert atmosphere; | A 81% B 18% |
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
2,2-Dimethyl-1,3-propanediol
(dimethyl-2,2 propanediyldioxy-1,3)-1,1 methyl-8a octahydro-1,2,3,4,6,7,8,8a oxo-6 naphtalene
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In diethyl ether at 0℃; for 5h; | 80% |
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
tert-butyldimethylsilyl chloride
A
5-(tert-butyl-dimethyl-silanyloxy)-4a-methyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one
Conditions | Yield |
---|---|
Stage #1: (S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione With sodium tetrahydroborate In methanol; dichloromethane at -78℃; Reduction; Stage #2: tert-butyldimethylsilyl chloride With 1H-imidazole In N,N-dimethyl-formamide at 45℃; Etherification; | A 75% B 10% |
chloro-trimethyl-silane
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
methyllithium
Conditions | Yield |
---|---|
Stage #1: (S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione; methyllithium With N,N,N,N,N,N-hexamethylphosphoric triamide; copper(l) iodide; chloro-trimethyl-silane In 1,2-dimethoxyethane; diethyl ether at 0℃; for 1h; Inert atmosphere; Stage #2: With Oxone; 18-crown-6 ether; sodium hydrogencarbonate In dichloromethane; water; acetone at 0℃; for 1h; Inert atmosphere; Stage #3: chloro-trimethyl-silane In pyridine Inert atmosphere; | 75% |
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
2,2,7,7-tetramethyl-3,6-dioxa-2,7-disilaoctane
A
(8aS)-1,1-(1,2-ethylenedioxy)-1,2,3,4,6,7,8,8a-octahydro-8a-methyl-6-oxonaphthalene
B
C15H22O4
Conditions | Yield |
---|---|
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78 - -10℃; for 8.5h; | A 73% B 6.3% |
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78℃; for 8.5h; | A 73% B 6.3% |
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
trifluoromethylsulfonic anhydride
Trifluoro-methanesulfonic acid (S)-8a-methyl-6-oxo-3,4,6,7,8,8a-hexahydro-naphthalen-1-yl ester
Conditions | Yield |
---|---|
With 2,6-di-tert-butyl-4-methylpyridine In dichloromethane at 0 - 20℃; for 1.5h; | 70% |
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide
D
Trifluoro-methanesulfonic acid (S)-8a-methyl-6-oxo-3,4,6,7,8,8a-hexahydro-naphthalen-1-yl ester
Conditions | Yield |
---|---|
Stage #1: (S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃; for 3h; Stage #2: N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide In tetrahydrofuran at 20℃; for 1h; | A 4.5% B 2.3% C 5.3% D 69% |
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
Propargylamine
Conditions | Yield |
---|---|
sodium tetrachloroaurate dihydrate In ethanol at 78℃; for 24h; | 68% |
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
6a-methyl-6,6a,9,10-tetrahydro-5H-tetrazolo<5,1-b><3>benzazepin-7(8H)-one
Conditions | Yield |
---|---|
With trimethylsilyl trifluoromethanesulfonate; trimethylsilylazide In dichloromethane for 18h; Ambient temperature; | 67% |
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
2,2,7,7-tetramethyl-3,6-dioxa-2,7-disilaoctane
A
(8aS)-1,1-(1,2-ethylenedioxy)-1,2,3,4,6,7,8,8a-octahydro-8a-methyl-6-oxonaphthalene
B
(S)-4a-methyl-4,4a,6,7-tetrahydro-1H-spiro[naphthalene-2,2'-[1,3]dioxolan]-5(3H)-one
C
C15H22O4
Conditions | Yield |
---|---|
With trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78℃; for 51h; Yields of byproduct given; | A n/a B 65% C n/a |
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
diethyl chlorophosphate
Conditions | Yield |
---|---|
Stage #1: (S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hexamethyldisilazane In tetrahydrofuran at -78 - 20℃; for 2.5h; Stage #2: diethyl chlorophosphate In tetrahydrofuran at 20℃; for 0.416667h; | A 4% B 61% |
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
ethylene glycol
(1S,6R)-8,8-ethylenedioxy-1-methylbicyclo[4.4.0]decan-2-one
Conditions | Yield |
---|---|
Stage #1: ethylene glycol With 5%-palladium/activated carbon; hydrogen; palladium dichloride at 20℃; for 0.25h; Stage #2: (S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione In tetrahydrofuran at 20℃; for 48h; | 60% |
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
chlorophosphoric acid diphenyl ester
Conditions | Yield |
---|---|
Stage #1: (S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 2h; Stage #2: chlorophosphoric acid diphenyl ester In tetrahydrofuran at 0℃; for 0.333333h; | A 19% B 53% C 5% |
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
diethyl chlorophosphate
Conditions | Yield |
---|---|
Stage #1: (S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 2h; Stage #2: diethyl chlorophosphate In tetrahydrofuran at 0℃; for 0.333333h; | A 16% B 50% C 14% |
(S)-8a-methyl-3,4,8,8a-tetrahydro-2H,7H-naphthalene-1,6-dione
ethylene glycol
(S)-4'a-Methyl-4',4'a,6',7'-tetrahydro-1'H,3'H-spiro[[1,3]dioxolane-2,2'-naphthalen]-5'-one
Conditions | Yield |
---|---|
With 2,4,6-collidinium p-toluenesulfonate In toluene for 48h; Inert atmosphere; Reflux; | 44% |
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