Conditions | Yield |
---|---|
With methylaluminum bis(2,6-di-tert-butylphenoxide) In diethyl ether; toluene at -78℃; for 2h; | 100% |
In diethyl ether at 0 - 20℃; | 87% |
Stage #1: ethylmagnesium bromide; benzaldehyde In tetrahydrofuran at 30℃; for 24h; Inert atmosphere; Stage #2: With water In tetrahydrofuran Inert atmosphere; | 73% |
Conditions | Yield |
---|---|
With potassium hydride; ditriptylethylborane In tetrahydrofuran for 0.0833333h; | 100% |
With zirconium dioxide hydrate; isopropyl alcohol at 130℃; for 0.5h; Meerwein-Ponndorf-Verley Reduction; | 100% |
With hydrogen In methanol at 40℃; for 24h; chemoselective reaction; | 100% |
Conditions | Yield |
---|---|
With C35H41ClFeIrPS; hydrogen; sodium methylate In tetrahydrofuran at 25℃; under 22502.3 Torr; for 2h; Reagent/catalyst; Autoclave; Inert atmosphere; | 100% |
With sodium tetrahydroborate; C11H18Cl2CoN2S; hydrogen In isopropyl alcohol at 100℃; under 37503.8 Torr; for 16h; Glovebox; Autoclave; | 97% |
With 1,1'-bis(diphenylphosphino)ferrocene; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; Butane-1,4-diol; potassium tert-butylate at 110℃; for 24h; Inert atmosphere; | 92% |
2-(1-phenyl-propoxy)-tetrahydro-pyran
1-Phenyl-1-propanol
Conditions | Yield |
---|---|
silica-supported prop-1-ylsulfonic acid In methanol | 99.6% |
With tetra-N-butylammonium tribromide In methanol at 20℃; for 1h; | 97% |
With tetra-N-butylammonium tribromide In methanol for 1.2h; | 97% |
With trichloroisocyanuric acid In methanol at 20℃; for 4h; | 92% |
Conditions | Yield |
---|---|
With (1R,2S)-2-aminomethyl-2-hydroxy-1,7,7-trimethylbicyclo[2.2.1]heptane In hexane for 48h; | 99% |
With polystyrene bond triphenylphosphonium chloride In toluene at 0 - 23℃; Inert atmosphere; chemoselective reaction; | 99% |
With 15-crown-5; sodium iodide In toluene at 0 - 23℃; for 24h; Reagent/catalyst; Solvent; Inert atmosphere; Schlenk technique; | 99% |
Conditions | Yield |
---|---|
With hydrogen; TMSB; palladium In ethanol at 20℃; under 760 Torr; for 20h; | 98% |
With riboflavin tetrabutyrate; oxygen; hydrazine hydrate In acetonitrile at 30℃; under 760.051 Torr; for 30h; | 92% |
With oxygen; hydrazine hydrate; riboflavin 2’,3’,4’,5’-tetrabutanoate In acetonitrile at 25 - 30℃; for 30h; chemoselective reaction; | 92% |
Conditions | Yield |
---|---|
With titanium tetrachloride In dichloromethane at -78 - -30℃; Product distribution; further aldehydes and tetraalkylleads; reaction with mixed tetraalkylleads; other conditions; | 98% |
With titanium tetrachloride In dichloromethane at -78 - -30℃; | 98% |
With titanium tetrachloride In dichloromethane at -78 - -30℃; | 96% |
triethyl-butyl plumbane
benzaldehyde
A
1-Phenyl-1-propanol
B
1-Phenyl-1-pentanol
Conditions | Yield |
---|---|
With titanium tetrachloride In dichloromethane at -78 - -30℃; | A 98% B 1.7% |
1-phenyl-1-tert-butyldimethylsiloxypropane
1-Phenyl-1-propanol
Conditions | Yield |
---|---|
With tetra-N-butylammonium tribromide In methanol for 7h; | 98% |
With N-iodo-succinimide In methanol at 20℃; for 19h; | 95% |
With methanol at 20℃; for 3.33333h; | 93% |
sulfonic acid functionalized nanoporous silica In methanol at 35℃; for 12h; | 87% |
With tetrabutyl ammonium fluoride |
Conditions | Yield |
---|---|
In toluene for 0.166667h; Alkylation; reduction; Title compound not separated from byproducts.; | A 97% B 2% |
Conditions | Yield |
---|---|
In toluene for 24h; Alkylation; reduction; Title compound not separated from byproducts.; | A 97% B 2% |
Conditions | Yield |
---|---|
In diethyl ether Heating; | 96% |
With diethyl ether | |
With 2,3-Dimethylaniline; benzene |
Conditions | Yield |
---|---|
With iron(III) sulfate; water In toluene at 110℃; for 1h; Ionic liquid; | 96% |
In ethanol at 25℃; Rate constant; Kinetics; Thermodynamic data; ΔH(excit.), ΔS(excit.); |
Conditions | Yield |
---|---|
With potassium hydroxide; hydrogen; Aliquat 336; palladium on activated charcoal In 2,2,4-trimethylpentane at 50℃; for 0.833333h; Product distribution; various time, solvents; also in the presence of various aromatic halides as promoters; further benzylic alcohols; | A 96% B 4% |
1-phenylpropylene oxide
1-Phenyl-1-propanol
Conditions | Yield |
---|---|
With sodium tert-pentoxide; sodium hydride; zinc(II) chloride In 1,2-dimethoxyethane at 65℃; for 6h; | 95% |
1-phenylpropyl trimethylsilyl ether
1-Phenyl-1-propanol
Conditions | Yield |
---|---|
With silica triflate In methanol for 0.0666667h; Heating; | 95% |
With 1-butyl-3-methylimidazolium chloride at 20℃; for 1.33h; | 94% |
With silica gel; iodic acid In water for 0.00833333h; microwave irradiation; | 90% |
1-Phenyl-1-propanol
Conditions | Yield |
---|---|
With silica gel In methanol for 4h; Reflux; | 95% |
With sodium hydroxide In tetrahydrofuran; diethyl ether; water at 20℃; for 0.5h; | |
With silica gel In methanol at 60℃; for 6h; Inert atmosphere; Schlenk technique; Glovebox; | |
With air In diethyl ether | 129 mg |
With dihydrogen peroxide; sodium hydroxide Inert atmosphere; | 145 mg |
Conditions | Yield |
---|---|
With dibutylmagnesium; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In toluene at 75℃; for 24h; regioselective reaction; | 95% |
Conditions | Yield |
---|---|
Stage #1: ethyl iodide With 1-butylpyridinium bromide; N-butylpyridinium tetrafluoroborate; zinc at 50℃; for 1h; Stage #2: benzaldehyde at 20℃; for 12h; | 94% |
Stage #1: ethyl iodide With magnesium In diethyl ether Inert atmosphere; Stage #2: benzaldehyde In diethyl ether at 0 - 20℃; for 2h; Grignard Reaction; Inert atmosphere; | 84% |
Stage #1: ethyl iodide With N-butylpyridinium tetrafluoroborate at 20℃; for 1h; Stage #2: benzaldehyde With pyridine at 20℃; for 12h; Further stages.; | 83% |
With diethyl ether; calcium |
Conditions | Yield |
---|---|
In toluene for 0.25h; Alkylation; | 94% |
Conditions | Yield |
---|---|
With hydrogen In ethanol; water at 120℃; under 37503.8 Torr; chemoselective reaction; | 94% |
Conditions | Yield |
---|---|
With C20H24B10Cl4FeN6; dihydrogen peroxide In methanol at 20℃; for 6h; | 93% |
With lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); oxygen Kinetics; relative chain propagation rates; | |
With NADPH In dimethyl sulfoxide at 30℃; pH=7.4; Product distribution; Further Variations:; Reagents; | 99 % Chromat. |
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)nickel (0); tri-tert-butyl phosphine; 1-(Prop-2-enyl)-1,2,3,4,5-pentamethylcyclopenta-2,4-dien In hexane; toluene at 0℃; for 24h; | 93% |
With tri-tert-butyl phosphine; bis(1,5-cyclooctadiene)nickel (0) In hexane; water at 20℃; for 20h; Product distribution; Further Variations:; Catalysts; Reagents; Solvents; | 81% |
With tetra-(n-butyl)ammonium iodide In tetrahydrofuran; N,N-dimethyl-formamide for 7h; Ambient temperature; electrolysis with Pt/Cu electrodes; | 74% |
Conditions | Yield |
---|---|
With C35H41FePRhS; hydrogen; sodium methylate In tetrahydrofuran at 82℃; under 22502.3 Torr; for 16h; Autoclave; Inert atmosphere; | A 7% B 93% |
With triethylamine; palladium on activated charcoal In toluene at 150℃; for 3h; | A 5 % Spectr. B 91 % Spectr. |
With dichloro(η3:η2:η3-dodeca-2,6,10-triene-1,12-diyl)ruthenium(IV); water; sodium formate at 100℃; for 24h; Inert atmosphere; | A 82 %Chromat. B n/a |
Conditions | Yield |
---|---|
With alkaline hydrogen peroxide; lithium triethylborohydride In tetrahydrofuran for 1h; | 92% |
(E)-3-(N,N-dimethylamino)-1-phenyl-2-propen-1-one
1-Phenyl-1-propanol
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; for 12h; Reagent/catalyst; Temperature; | 92% |
potassium trifluoro(1-phenylpropan-2-yl)borate
1-Phenyl-1-propanol
Conditions | Yield |
---|---|
With rose bengal; triethylamine In ethanol at 25℃; for 12h; Schlenk technique; Irradiation; | 91% |
Conditions | Yield |
---|---|
With lithium In tetrahydrofuran at -30℃; for 0.25h; | 90% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 0.0833333h; | 90% |
In tetrahydrofuran at 20℃; further carbonyl compounds, further solvents, further Grignard/TDA-1 complexes; | 90% |
Conditions | Yield |
---|---|
With silica-supported Jones reagent In dichloromethane for 0.00269444h; | 100% |
With ruthenium trichloride; iodobenzene; potassium peroxomonosulfate In water; acetonitrile at 20℃; for 0.3h; | 100% |
With ruthenium trichloride; iodobenzene; potassium peroxymonosulfate In water; acetonitrile at 20℃; for 0.3h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
indium(III) chloride at 20℃; for 1h; | 100% |
With pyridine | 99% |
With SiO2-supported Co(II) Salen complex catalyst at 50℃; for 0.75h; | 99% |
Conditions | Yield |
---|---|
Stage #1: ethyl iodide With magnesium; N-butylpyridinium tetrafluoroborate at 20℃; for 1h; Stage #2: 1-Phenyl-1-propanol With magnesium iodide at 20℃; for 12h; Further stages.; | 100% |
Conditions | Yield |
---|---|
In diethyl ether at 0 - 20℃; | 100% |
1-Phenyl-1-propanol
chloromethyldiphenylsilane
1-phenylpropan-1-yl diphenylmethylsilyl ether
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 20℃; for 2h; Inert atmosphere; | 100% |
3,4-dihydro-2H-pyran
1-Phenyl-1-propanol
2-(1-phenyl-propoxy)-tetrahydro-pyran
Conditions | Yield |
---|---|
silica-supported prop-1-ylsulfonic acid In acetonitrile for 0.166667h; | 99.8% |
With C8H15N2O3S(1+)*Cl5Zn2(1-) In neat (no solvent) at 20℃; for 0.75h; Green chemistry; | 92% |
With trichloroisocyanuric acid at 60 - 80℃; for 6h; | 90% |
bismuth(III) nitrate In dichloromethane at 20℃; for 0.3h; | 90% |
With tetra-N-butylammonium tribromide In dichloromethane at 20℃; for 0.41h; | 85% |
Conditions | Yield |
---|---|
Stage #1: 1-Phenyl-1-propanol With sodium hydride In tetrahydrofuran at 20℃; for 1h; Stage #2: methyl iodide at 20℃; | 99.2% |
Conditions | Yield |
---|---|
With chloro-trimethyl-silane; acetonitrile; sodium iodide In hexane for 24h; Ambient temperature; | 99% |
With chloro-trimethyl-silane; acetonitrile; sodium iodide In hexane for 24h; Ambient temperature; | 99% |
With hydrogen In ethanol at 80℃; under 2250.23 Torr; for 3h; Catalytic behavior; Temperature; Solvent; Inert atmosphere; | 94% |
Isopropenyl acetate
1-Phenyl-1-propanol
(R)-1-phenylpropyl acetate
Conditions | Yield |
---|---|
With dicarbonylchlorido(pentabenzylcyclopentadienyl)ruthenium; potassium tert-butylate; sodium carbonate In tetrahydrofuran; toluene at 23℃; for 9h; Inert atmosphere; dynamic kinetic resolution; Enzymatic reaction; optical yield given as %ee; enantioselective reaction; | 99% |
With Candida antarctica lipase B; potassium tert-butylate; sodium carbonate; [chlorodicarbonyl(η-pentaphenylcyclopentadienyl)]Ru(II) In toluene at 20℃; for 17h; | 90% |
Stage #1: Isopropenyl acetate; 1-Phenyl-1-propanol With Novozym 435 In toluene at 60℃; for 1h; Enzymatic reaction; Stage #2: In toluene at 60℃; for 21h; | n/a |
1-Phenyl-1-propanol
(-)-(S)-(1-chloropropyl)benzene
Conditions | Yield |
---|---|
With 1,3,5-trichloro-2,4,6-triazine; dimethyl sulfoxide at 20℃; for 0.416667h; chemoselective reaction; | 99% |
Conditions | Yield |
---|---|
Stage #1: 1-Phenyl-1-propanol With allylchloro[1,3-bis(2,6-di-isopropylphenyl)imidazol-2-ylidine]palladium(II); para-chlorotoluene; potassium tert-butylate In toluene at 40℃; for 2.5h; Inert atmosphere; Stage #2: 2,6-dimethyl-1-chlorobenzene In toluene at 80℃; for 2h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With allylchloro[1,3-bis(2,6-di-isopropylphenyl)imidazol-2-ylidine]palladium(II); potassium tert-butylate In toluene at 80℃; for 1.5h; Inert atmosphere; | 99% |
1-Phenyl-1-propanol
5,5-dimethyl-2-phenyl-1,3,2-dioxaborinane
1,1-Diphenyl-propan-1-ol
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)nickel (0); potassium tert-butylate; chlorobenzene; cesium fluoride; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In toluene at 80℃; for 4h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
Stage #1: 1-Phenyl-1-propanol; benzoic acid With N-Bromosuccinimide In 1,4-dioxane at 60℃; for 1h; Sealed tube; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In 1,4-dioxane at 60℃; for 2h; Reagent/catalyst; Solvent; Temperature; | 99% |
Stage #1: 1-Phenyl-1-propanol; benzoic acid With N-Bromosuccinimide In 1,4-dioxane at 60℃; for 1h; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In 1,4-dioxane for 2h; | 99% |
Stage #1: 1-Phenyl-1-propanol; benzoic acid With N-Bromosuccinimide In 1,4-dioxane at 60℃; for 1h; Stage #2: With 1,8-diazabicyclo[5.4.0]undec-7-ene In 1,4-dioxane for 2h; | 99% |
With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide In water; ethyl acetate at 100℃; for 12h; Catalytic behavior; Reagent/catalyst; Solvent; Schlenk technique; | 72% |
Conditions | Yield |
---|---|
With C24H24IrN4O4(1+)*BF4(1-); sodium t-butanolate at 140℃; for 24h; Sealed tube; Inert atmosphere; | 99% |
With caesium carbonate at 150℃; for 24h; | 87% |
With carbonylhydrido(tetrahydroborato)[bis(2-diphenylphosphinoethyl)amino]ruthenium(II); sodium methylate at 150℃; for 20h; Inert atmosphere; Autoclave; Glovebox; Green chemistry; | 83 %Spectr. |
With trimethylamine-N-oxide; (1,4-dimethyl-5,7-diphenyl-1,2,3,4-tetrahydro-6H-cyclopenta[b]pyrazin-6-one) irontricarbonyl complex3; sodium hydroxide at 130℃; for 24h; | 12 %Spectr. |
Conditions | Yield |
---|---|
With potassium hydroxide | 98.4% |
With dmap; triethylamine In tetrahydrofuran; dichloromethane Heating; | 84% |
1-Phenyl-1-propanol
1,1,1,3,3,3-hexamethyl-disilazane
1-phenylpropyl trimethylsilyl ether
Conditions | Yield |
---|---|
With polyvinylpolypyrrolidonium tribromide In acetonitrile at 20℃; for 0.116667h; | 98% |
With L-Aspartic acid In acetonitrile at 20℃; for 0.0666667h; | 98% |
With bismuth(lll) trifluoromethanesulfonate at 20℃; for 0.0333333h; Neat (no solvent); | 96% |
Conditions | Yield |
---|---|
With aluminum dodecatungstophosphate at 20℃; for 0.166667h; | 98% |
Conditions | Yield |
---|---|
Stage #1: succinic acid anhydride; 1-Phenyl-1-propanol With dmap In dichloromethane at 20℃; for 2h; Inert atmosphere; Stage #2: With hydrogenchloride In water | 98% |
With dmap In dichloromethane at 20℃; Inert atmosphere; |
2-methylchlorobenzene
1-Phenyl-1-propanol
2-(2-methylphenyl)-1-phenylpropan-1-one
Conditions | Yield |
---|---|
With allylchloro[1,3-bis(2,6-di-isopropylphenyl)imidazol-2-ylidine]palladium(II); potassium tert-butylate In toluene at 80℃; for 4h; Inert atmosphere; | 98% |
1. | orl-rat LD50:1600 mg/kg | ARZNAD Arzneimittel-Forschung. Drug Research. 12 (1962),347. | ||
2. | orl-mus LD50:500 mg/kg | AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. 116 (1958),154. | ||
3. | scu-mus LD50:700 mg/kg | AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. 116 (1958),154. |
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