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CAS No.: | 38345-66-3 |
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Name: | (2S,3R)-(+)-4-DIMETHYLAMINO-1,2-DIPHENYL-3-METHYL-2-BUTANOL |
Article Data: | 9 |
Molecular Structure: | |
Formula: | C19H25 N O |
Molecular Weight: | 283.414 |
Synonyms: | Benzeneethanol,a-[2-(dimethylamino)-1-methylethyl]-a-phenyl-, [S-(R*,S*)]-;(+)-Darvon alcohol; (+)-Oxyphene;(2S,3R)-(+)-4-(Dimethylamino)-3-methyl-1,2-diphenyl-2-butanol;(2S,3R)-(+)-4-Dimethylamino-1,2-diphenyl-3-methyl-2-butanol; Chirald; Darvonalcohol; Mosher's reagent; d-Oxyphene |
EINECS: | 204-765-3 |
Density: | 1.043 g/cm3 |
Melting Point: | 54-56 °C(lit.) |
Boiling Point: | 418.7 °C at 760 mmHg |
Flash Point: | 160.2 °C |
Appearance: | WHITE TO YELLOW POWDER, CRYSTALS OR SOLID |
PSA: | 23.47000 |
LogP: | 3.31460 |
(2RS,3SR)-4-dimethylamino-3-methyl-1,2-diphenyl-butan-2-ol
(2S,3R)-(+)-4-Dimethylamino-1,2-diphenyl-3-methyl-2-butanol
Conditions | Yield |
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With camphor-10-sulfonic acid |
dimethyl amine
p-toluenesulfonyl chloride
(2S,3R)-(+)-4-Dimethylamino-1,2-diphenyl-3-methyl-2-butanol
Conditions | Yield |
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In dimethyl sulfoxide for 48h; Ambient temperature; |
formaldehyd
(2S,3R)-(+)-4-Dimethylamino-1,2-diphenyl-3-methyl-2-butanol
Conditions | Yield |
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With formic acid |
lithium aluminium tetrahydride
benzoylferrocene
(2S,3R)-(+)-4-Dimethylamino-1,2-diphenyl-3-methyl-2-butanol
Conditions | Yield |
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With hydrogenchloride; ammonium chloride In diethyl ether (Ar); soln. of Chirald in Et2O stirred at 0°C, added to soln. of LiAlH4 in ether, cooled to -70°C; dropwise addn. of ethereal soln. of Fe-complex at -70°C; treatment with wet ether and aq. NH4Cl;; ethereal ext. treated with 1 N HCl; crystn. (hexane); | 90% |
lithium aluminium tetrahydride
(2S,3R)-(+)-4-Dimethylamino-1,2-diphenyl-3-methyl-2-butanol
Conditions | Yield |
---|---|
With hydrogenchloride; ammonium chloride In diethyl ether (Ar); soln. of Chirald in Et2O stirred at 0°C added to soln. of LiAlH4 in ether cooled to -70°C; dropwise addn. of ethereal soln. of Ru-complex at -50°C; treatment with wet ether and aq. NH4Cl;; ethereal ext. treated with 1 N HCl; crystn. (hexane); | 90% |
(2S,3R)-(+)-4-Dimethylamino-1,2-diphenyl-3-methyl-2-butanol
binaphthol chlorophosphite
(1'S,2'R)-2-(1'-benzyl-3'-dimethylamino-2'-methyl-1'-phenyl-propoxy)dinaphtho[2,1-d:1',2'-f](1,3,2) dioxaphosphepine
Conditions | Yield |
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With triethylamine In toluene | 89% |
(2S,3R)-(+)-4-Dimethylamino-1,2-diphenyl-3-methyl-2-butanol
Conditions | Yield |
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With triethylamine In toluene | 87% |
(2S,3R)-(+)-4-Dimethylamino-1,2-diphenyl-3-methyl-2-butanol
1-dodecylbromide
(+)-(2R,3S)-N-(3-hydroxy-2-methyl-3,4-diphenylbutyl)-N,N-dimethyldodecan-1-ammonium bromide
Conditions | Yield |
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In acetonitrile for 240h; Reflux; | 65% |
(2S,3R)-(+)-4-Dimethylamino-1,2-diphenyl-3-methyl-2-butanol
benzyl chloride
Conditions | Yield |
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In ethanol for 18h; Heating; | 28% |
methyl 2-oxo-2-phenylacetate
(2S,3R)-(+)-4-Dimethylamino-1,2-diphenyl-3-methyl-2-butanol
lithium tetrabutylaluminate
α-butyl-α-hydroxy phenyl methyl ester
Conditions | Yield |
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With hydrogenchloride In hexane at 0℃; for 2h; asymmetric alkylation; various solvent; | |
With hydrogenchloride Multistep reaction; |