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Neopinone CAS:509-66-0 Qingdao Belugas Import and Export Co., Ltd. is a scientific and technological company integrating research and development, production and trade of chemical intermediates, specializing in high quality organic intermediates, st
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inquiryfactory?direct?saleAppearance:White powder Storage:Sealed and preserved Package:200/Kilograms Application:healing drugs Transportation:By sea Port:Shanghai/tianjin
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United Scientific Company Located in Shanghai of China , is a competitive player in the global specialty and fine chemical market. Fenghua has both the expertise and flexibility to produce a wide range of chemicals. Focusing on developing the innovat
neopinoneAppearance:Off white to slight yellow solid Storage:Store in dry and cool condition Package:25kg or according to cutomer's demand Application:Chemical research/Pharmaceutical intermediates Transportation:By Sea,by Air,By courier like DHL or
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(+)-14β-bromocodeinone
(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In methanol; chloroform under 760 Torr; for 5h; Ambient temperature; |
neopinone dimethyl acetal
(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one
Conditions | Yield |
---|---|
With hydrogenchloride |
thebaine
(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: N-bromo-acetamide 2: H2, aq. NaOH / Pd-C / methanol 3: aq. HCl View Scheme | |
Multi-step reaction with 2 steps 1: NBS / acetone; H2O 2: H2 / Pd-C / CHCl3; methanol / 5 h / 760 Torr / Ambient temperature View Scheme |
14-bromo-4,5α-epoxy-3-methoxy-17-methyl-(14ξ)-morphin-7-en-6-one; hydrochloride
(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one
Conditions | Yield |
---|---|
With sodium sulfite |
3a(R),9b(S)-dihydro-5-methoxy-9b-<2-(N-methylammonio)ethyl>phenanthro<4,4a,4b,5-bcd>furan-3(8H)-one trifluoroacetate
A
(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one
C
codeinone
Conditions | Yield |
---|---|
With sodium hydrogencarbonate In chloroform; water for 0.333333h; Yield given. Yields of byproduct given; |
(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one
Conditions | Yield |
---|---|
With methanol; palladium on activated charcoal; chloroform |
codeine hydrochloride
A
(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one
B
codeinone
Conditions | Yield |
---|---|
With alcohol dehydrogenase from Thermoanaerobium brockii; β-nicotinamide dinucleotide phosphate sodium salt; morphine dehydrogenase from Pseudomonas putida M10 In phosphate buffer at 30℃; for 24h; Title compound not separated from byproducts.; |
codeine
A
(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one
B
codeinone
Conditions | Yield |
---|---|
With β-nicotinamide dinucleotide phosphate sodium salt; NADP+-dependent morphine dehydrogenase; 1-(3-hydroxypropyl)-3-methylimidazolium glycolate; water In phosphate buffer at 30℃; for 24h; Title compound not separated from byproducts.; |
14-bromo-4,5α-epoxy-3,6,6-trimethoxy-17-methyl-(14ξ)-morphin-7-ene
(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: H2, aq. NaOH / Pd-C / methanol 2: aq. HCl View Scheme |
2-iodo-6-methoxy-3-(2,2-dimethoxyethyl)phenol
(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: tributylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 0.5 h / 20 °C 2.1: tris-(dibenzylideneacetone)dipalladium(0); triethylamine; tris-(o-tolyl)phosphine / acetonitrile / 1 h / 85 °C 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 70 °C 3.2: 0.17 h / 20 °C 4.1: camphor-10-sulfonic acid / methanol / 6 h / 20 °C 5.1: Dess-Martin periodane / dichloromethane / 0.5 h / 40 °C 6.1: trifluoroacetic acid / water; toluene / 2 h / 50 °C 7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 0 °C 8.1: mercaptoacetic acid; triethylamine / dichloromethane / 0.5 h / 0 °C 8.2: 0.5 h / 20 °C View Scheme | |
Multi-step reaction with 7 steps 1.1: tributylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 1 h / 20 °C 2.1: tris-(dibenzylideneacetone)dipalladium(0); tris-(o-tolyl)phosphine / acetonitrile / 2 h / 85 °C 3.1: camphor-10-sulfonic acid / methanol / 6 h / 20 °C 4.1: Dess-Martin periodane / dichloromethane / 0.5 h / 40 °C 5.1: trifluoroacetic acid / water; toluene / 2 h / 50 °C 6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 0 °C 7.1: mercaptoacetic acid; triethylamine / dichloromethane / 0.5 h / 0 °C 7.2: 0.5 h / 20 °C View Scheme |
(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1.1: acetyl chloride / methanol / 1 h / 40 °C 2.1: tributylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 0.5 h / 20 °C 3.1: tris-(dibenzylideneacetone)dipalladium(0); triethylamine; tris-(o-tolyl)phosphine / acetonitrile / 1 h / 85 °C 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 70 °C 4.2: 0.17 h / 20 °C 5.1: camphor-10-sulfonic acid / methanol / 6 h / 20 °C 6.1: Dess-Martin periodane / dichloromethane / 0.5 h / 40 °C 7.1: trifluoroacetic acid / water; toluene / 2 h / 50 °C 8.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 0 °C 9.1: mercaptoacetic acid; triethylamine / dichloromethane / 0.5 h / 0 °C 9.2: 0.5 h / 20 °C View Scheme | |
Multi-step reaction with 8 steps 1.1: acetyl chloride / methanol / 1 h / 40 °C 2.1: tributylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 1 h / 20 °C 3.1: tris-(dibenzylideneacetone)dipalladium(0); tris-(o-tolyl)phosphine / acetonitrile / 2 h / 85 °C 4.1: camphor-10-sulfonic acid / methanol / 6 h / 20 °C 5.1: Dess-Martin periodane / dichloromethane / 0.5 h / 40 °C 6.1: trifluoroacetic acid / water; toluene / 2 h / 50 °C 7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 0 °C 8.1: mercaptoacetic acid; triethylamine / dichloromethane / 0.5 h / 0 °C 8.2: 0.5 h / 20 °C View Scheme |
benzyl 2-((5R,6R)-5-(tert-butyldimethylsilyloxy)-6-(3-(2,2-dimethoxyethyl)-2-iodo-6-methoxyphenoxy)cyclohex-1-enyl)ethylcarbamate
(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: tris-(dibenzylideneacetone)dipalladium(0); triethylamine; tris-(o-tolyl)phosphine / acetonitrile / 1 h / 85 °C 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 70 °C 2.2: 0.17 h / 20 °C 3.1: camphor-10-sulfonic acid / methanol / 6 h / 20 °C 4.1: Dess-Martin periodane / dichloromethane / 0.5 h / 40 °C 5.1: trifluoroacetic acid / water; toluene / 2 h / 50 °C 6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 0 °C 7.1: mercaptoacetic acid; triethylamine / dichloromethane / 0.5 h / 0 °C 7.2: 0.5 h / 20 °C View Scheme |
benzyl N-[2-[(5aR,6R,9aS)-6-(tert-butyldimethylsilyloxy)-6,7-dihydro-1-(2,2-dimethoxyethyl)-4-methoxy-9a(5aH)-dibenzofuranyl]ethyl]carbamate
(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 70 °C 1.2: 0.17 h / 20 °C 2.1: camphor-10-sulfonic acid / methanol / 6 h / 20 °C 3.1: Dess-Martin periodane / dichloromethane / 0.5 h / 40 °C 4.1: trifluoroacetic acid / water; toluene / 2 h / 50 °C 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 0 °C 6.1: mercaptoacetic acid; triethylamine / dichloromethane / 0.5 h / 0 °C 6.2: 0.5 h / 20 °C View Scheme |
C32H45N3O11SSi
(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: camphor-10-sulfonic acid / methanol / 6 h / 20 °C 2.1: Dess-Martin periodane / dichloromethane / 0.5 h / 40 °C 3.1: trifluoroacetic acid / water; toluene / 2 h / 50 °C 4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 0 °C 5.1: mercaptoacetic acid; triethylamine / dichloromethane / 0.5 h / 0 °C 5.2: 0.5 h / 20 °C View Scheme |
N-[2-[(5aR,6R,9aS)-6,7-dihydro-6-hydroxy-1-(2,2-dimethoxyethyl)-4-methoxy-9a(5aH)-dibenzofuranyl]ethyl]-N-methyl-2,4-dinitrobenzenesulfonamide
(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: Dess-Martin periodane / dichloromethane / 0.5 h / 40 °C 2.1: trifluoroacetic acid / water; toluene / 2 h / 50 °C 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 0 °C 4.1: mercaptoacetic acid; triethylamine / dichloromethane / 0.5 h / 0 °C 4.2: 0.5 h / 20 °C View Scheme |
N-[2-[(5aR,9aS)-6,7-dihydro-1-(2,2-dimethoxyethyl)-4-methoxy-6-oxo-9a(5aH)-dibenzofuranyl]ethyl]-N-methyl-2,4-dinitrobenzenesulfonamide
(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: trifluoroacetic acid / water; toluene / 2 h / 50 °C 2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 0 °C 3.1: mercaptoacetic acid; triethylamine / dichloromethane / 0.5 h / 0 °C 3.2: 0.5 h / 20 °C View Scheme |
C24H23N3O10S
(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 0 °C 2.1: mercaptoacetic acid; triethylamine / dichloromethane / 0.5 h / 0 °C 2.2: 0.5 h / 20 °C View Scheme |
N-[2-[(3aR,9RS,9bS)-3a,8,9,9a-tetrahydro-9-(methanesulfonyloxy)-5-methoxy-3-oxo-9b-phenanthro[4,5-bcd]furanyl]ethyl]-N-methyl-2,4-dinitrobenzenesulfonamide
A
(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one
B
codeinone
Conditions | Yield |
---|---|
Stage #1: N-[2-[(3aR,9RS,9bS)-3a,8,9,9a-tetrahydro-9-(methanesulfonyloxy)-5-methoxy-3-oxo-9b-phenanthro[4,5-bcd]furanyl]ethyl]-N-methyl-2,4-dinitrobenzenesulfonamide With mercaptoacetic acid; N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.5h; Stage #2: With sodium carbonate In dichloromethane; water at 20℃; for 0.5h; |
C24H21N3O9S
A
(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one
B
codeinone
Conditions | Yield |
---|---|
Stage #1: C24H21N3O9S With mercaptoacetic acid; triethylamine In dichloromethane at 0℃; for 0.5h; Stage #2: With sodium carbonate In dichloromethane; water at 20℃; for 0.5h; |
N-[2-((5R,6R)-5-(tert-butyldimethylsilyloxy)-6-(3-(2,2-dimethoxyethyl)-2-iodo-6-methoxyphenoxy)cyclohex-1-enyl)]-N-methyl-2,4-dinitrobenzenesulfonamide
(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: tris-(dibenzylideneacetone)dipalladium(0); tris-(o-tolyl)phosphine / acetonitrile / 2 h / 85 °C 2.1: camphor-10-sulfonic acid / methanol / 6 h / 20 °C 3.1: Dess-Martin periodane / dichloromethane / 0.5 h / 40 °C 4.1: trifluoroacetic acid / water; toluene / 2 h / 50 °C 5.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 0 °C 6.1: mercaptoacetic acid; triethylamine / dichloromethane / 0.5 h / 0 °C 6.2: 0.5 h / 20 °C View Scheme |
(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: oxygen; 5,15,10,20-tetraphenylporphyrin / dichloromethane / 4 h / 20 °C / Irradiation 2: triethylamine / dichloromethane / 0.17 h / 20 °C 3: Martins sulfurane / dichloromethane / 0.17 h / 0 °C 4: N-ethyl-N,N-diisopropylamine; thiophenol / dichloromethane / 0.67 h / 0 °C View Scheme |
(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Martins sulfurane / dichloromethane / 0.17 h / 0 °C 2: N-ethyl-N,N-diisopropylamine; thiophenol / dichloromethane / 0.67 h / 0 °C View Scheme |
A
(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one
B
codeinone
Conditions | Yield |
---|---|
With thiophenol; N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.666667h; Overall yield = 50.5 %; Overall yield = 53.5 mg; |
(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 0.17 h / 20 °C 2: Martins sulfurane / dichloromethane / 0.17 h / 0 °C 3: N-ethyl-N,N-diisopropylamine; thiophenol / dichloromethane / 0.67 h / 0 °C View Scheme |
codeine
A
(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one
B
codeinone
C
Neopin
Conditions | Yield |
---|---|
With NADP In aq. buffer at 30℃; for 10.6667h; pH=9; Reagent/catalyst; Enzymatic reaction; |
(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one
Oxycodone
Conditions | Yield |
---|---|
With phenylsilane; oxygen; cobalt acetylacetonate In tetrahydrofuran for 12h; | 97% |
methyllithium
(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one
Conditions | Yield |
---|---|
In toluene |
(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one
isoneopine
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol | |
With potassium hydroxide; sodium tetrahydroborate In water |
(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one
Neopin
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol | |
With lithium triethylborohydride In tetrahydrofuran |
(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one
codeinone
7,8-didehydro-4-hydroxy-3-methoxy-17-methyl-morphinan-6-one
Conditions | Yield |
---|---|
With ammonium chloride; zinc In ethanol |
(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one
benzene
Conditions | Yield |
---|---|
(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one
6β-acetoxy-4,5α-epoxy-3-methoxy-17-methyl-morphin-8(14)-ene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aq. NaBH4 / methanol 2: 3 h / 80 - 85 °C View Scheme |
(4R,7aR,12bS)-9-methoxy-3-methyl-2,3,4,6-tetrahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7(7aH)-one
dihydro-isocodeine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aq. NaBH4 / methanol 2: H2, aq. HCl / PtO2 / 8 h / 760 Torr / Ambient temperature View Scheme |
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