Conditions | Yield |
---|---|
With diethoxymethylane; cesium fluoride at 25℃; for 5h; | 100% |
With diethoxymethylane; ethyl laurate; cesium fluoride at 25℃; for 5h; | 100% |
With C28H18Co(1-)*K(1+)*2C4H10O2; hydrogen In toluene at 60℃; under 8025.8 Torr; for 24h; chemoselective reaction; | 99% |
tert-butyl-(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro-decyloxy)-(1-methyl-2-phenyl-ethoxy)-phenyl-silane
3-phenyl-2-propanol
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 3h; deprotection; | 100% |
3-phenyl-2-propanol
Conditions | Yield |
---|---|
With SO3H silica gel at 25℃; for 0.5h; | 100% |
Conditions | Yield |
---|---|
With sodium tetrahydroborate; alpha cyclodextrin In water for 24h; Product distribution; Ambient temperature; presence of β-, and γ-cyclodextrin; kinetic resolution; further epoxides; | 98% |
Stage #1: 1,2-epoxy-3-phenylpropane With sodium tetrahydroborate; diselenide resin In ethanol Stage #2: With 2,2'-azobis(isobutyronitrile); tris-(trimethylsilyl)silane | 97% |
With [carbonylchlorohydrido{bis[2-(diphenylphosphinomethyl)ethyl]amino}ethylamino] ruthenium(II); potassium tert-butylate; hydrogen In toluene at 100℃; under 37503.8 Torr; for 24h; regioselective reaction; | 95% |
3-phenyl-2-propanol
Conditions | Yield |
---|---|
With 3-azapentane-1,5-diamine at 160℃; for 0.5h; Reagent/catalyst; Sealed tube; Microwave irradiation; | 97% |
(±)-trans-(3-phenyloxiran-2-yl)methyl 4-methylbenzenesulfonate
3-phenyl-2-propanol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In diethyl ether at 0℃; | 95% |
1-phenylpropylene oxide
3-phenyl-2-propanol
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; under 760.051 Torr; for 2h; regioselective reaction; | 95% |
With ammonium formate In ethyl acetate at 25℃; for 12h; Inert atmosphere; | 94% |
With alkaline hydrogen peroxide; lithium triethylborohydride In tetrahydrofuran for 1h; | 93% |
With Al-trifluoromethanesulfonyldiisobutylalane In diethyl ether at 25℃; for 0.5h; Meerwein-Ponndorf-Verley reduction; Inert atmosphere; regioselective reaction; | |
Multi-step reaction with 2 steps 1: dimethyltitanocene / tetrahydrofuran / 18 h / Inert atmosphere; Reflux 2: water; potassium carbonate / tetrahydrofuran; acetone / 16 h / Inert atmosphere View Scheme |
(2-phenylpropan-1-yloxy)tetrahydro-2H-pyran
3-phenyl-2-propanol
Conditions | Yield |
---|---|
With silica triflate In methanol for 0.166667h; Heating; | 95% |
Conditions | Yield |
---|---|
In tetrahydrofuran A soln. of PhCH2COMe in THF was added to a suspn. of complex in THF at -78°C; 1 h;; evapd., chromy. on silica; eluent - ethyl acetate-light petroleum;; | A n/a B 95% |
Conditions | Yield |
---|---|
Stage #1: benzyl chloride With magnesium In diethyl ether Stage #2: acetaldehyde In diethyl ether at 20℃; for 2h; Grignard reaction; | 93% |
Conditions | Yield |
---|---|
Stage #1: methyloxirane; benzene With aluminium trichloride at 6 - 7℃; for 4h; Stage #2: With water Further stages.; | 93% |
Conditions | Yield |
---|---|
With aluminum oxide; sodium tetrahydroborate; palladium dichloride In hexane; water at 30℃; for 1h; | 93% |
With ammonia borane; C28H28Cl2CoNP2; erbium(III) triflate In tetrahydrofuran at 55℃; for 8h; Reagent/catalyst; | 93% |
In isopropyl alcohol at 29.84℃; under 760.051 Torr; for 6h; Inert atmosphere; UV-irradiation; Sealed tube; | 76% |
With cobalt(II) bis[bis((trifluoromethyl)sulfonyl)amide]; hydrogen; zinc trifluoromethanesulfonate In tetrahydrofuran at 80℃; under 30003 Torr; for 16h; Catalytic behavior; Autoclave; regioselective reaction; | 85 %Chromat. |
trimethyl[(1-phenylpropan-2-yl)oxy]silane
3-phenyl-2-propanol
Conditions | Yield |
---|---|
With trinitratocerium(IV) bromate at 20℃; for 0.0833333h; | 92% |
With tris[trinitratocerium(IV)] paraperiodate at 20℃; for 0.0166667h; | 90% |
formic acid
(+/-)-formic acid-(1-methyl-2-phenyl-ethyl ester)
3-phenyl-2-propanol
Conditions | Yield |
---|---|
Stage #1: formic acid With silica gel at 20℃; for 0.0166667h; Stage #2: (+/-)-formic acid-(1-methyl-2-phenyl-ethyl ester) With silica gel at 110℃; for 0.05h; | 92% |
3-phenyl-2-propanol
Conditions | Yield |
---|---|
With scandium tris(trifluoromethanesulfonate); trimethyleneglycol In acetonitrile for 2h; Heating; | 90% |
With bismuth(III) chloride; water In acetonitrile at 50℃; for 3h; | 78% |
bis-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-nonyl)-thiocarbamic acid O-(1-methyl-2-phenyl-ethyl) ester
B
3-phenyl-2-propanol
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at -78℃; for 1h; | A n/a B 90% |
[2-(benzyloxy)propyl]benzene
3-phenyl-2-propanol
Conditions | Yield |
---|---|
Stage #1: [2-(benzyloxy)propyl]benzene With isocyanate de chlorosulfonyle; sodium carbonate In dichloromethane for 20h; Heating; Stage #2: With sodium hydroxide In methanol at 20℃; for 1h; | 88% |
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at -78℃; for 1h; | A n/a B 88% |
Conditions | Yield |
---|---|
With pyridine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 4,4'-bipyridine; NiI2*3.9H2O; triethylamine hydrochloride; sodium iodide; zinc at 20℃; for 12h; | 87% |
Stage #1: bromobenzene With n-butyllithium In tetrahydrofuran; hexane at -70℃; Stage #2: methyloxirane In tetrahydrofuran; hexane at -50 - 20℃; | 72% |
Stage #1: bromobenzene With n-butyllithium In tetrahydrofuran at -30℃; for 0.5h; Stage #2: methyloxirane In tetrahydrofuran at 20℃; for 1h; Further stages.; | 68% |
Conditions | Yield |
---|---|
With formic acid; triethylamine; Pd0-EnCatTM In ethyl acetate at 23℃; for 3h; | 87% |
Conditions | Yield |
---|---|
With water; diphenyldisulfane; 9-(2-mesityl)-10-methylacridinium perchlorate In acetonitrile at 20℃; for 24h; Irradiation; Inert atmosphere; regioselective reaction; | 87% |
bis-(4,4,5,5,6,6,7,7,7-nonafluoro-heptyl)-thiocarbamic acid O-(1-methyl-2-phenyl-ethyl) ester
B
3-phenyl-2-propanol
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at -78℃; for 1h; | A n/a B 86% |
B
3-phenyl-2-propanol
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at -78℃; for 1h; | A n/a B 85% |
sodium tetraethylaluminate
1-phenyl-acetone
A
3-phenyl-2-propanol
B
2-methyl-1-phenyl-2-butanol
Conditions | Yield |
---|---|
nickel dichloride In pentane at 35℃; for 2h; | A 3% B 82% |
Conditions | Yield |
---|---|
With titanium(IV) isopropylate In diethyl ether for 6h; Product distribution; Ambient temperature; other Grignard reagents, var. time; | 80% |
With titanium(IV) isopropylate In diethyl ether for 6h; Ambient temperature; | 80% |
2-methyl-4,7-dihydro-1,3-dioxepine
phenylmagnesium bromide
A
3-phenyl-2-propanol
B
2-phenylmethyl-but-3-en-1-ol
Conditions | Yield |
---|---|
1,2-bis(diphenylphosphino)ethane nickel(II) chloride for 14h; Ambient temperature; | A n/a B 80% |
1-Phenylpropane-1,2-dione
A
3-phenyl-2-propanol
B
1-Phenyl-1-propanol
C
1-phenyl-1,2-propandiol
D
1-phenyl-propan-1-one
Conditions | Yield |
---|---|
With samarium diiodide; water In tetrahydrofuran at 20℃; for 0.166667h; Further byproducts given; | A 6% B 79% C 3% D 7% |
Conditions | Yield |
---|---|
In diethyl ether for 2h; -40 deg C to 0 deg C; | 74% |
3-phenyl-2-propanol
Conditions | Yield |
---|---|
Stage #1: phenyl(1-phenylpropan-2-yl)silane With tetrafluoroboric acid diethyl ether In dichloromethane at 0 - 25℃; for 2h; Schlenk technique; Inert atmosphere; Stage #2: With potassium fluoride; dihydrogen peroxide; potassium hydrogencarbonate In tetrahydrofuran; methanol; dichloromethane; water for 18h; Inert atmosphere; Schlenk technique; Reflux; | 72% |
Conditions | Yield |
---|---|
With periodic acid; pyridinium chlorochromate In acetonitrile at 0 - 23℃; for 2.08333h; Inert atmosphere; | 100% |
With periodic acid; pyridinium chlorochromate In acetonitrile at 0 - 23℃; for 2h; Inert atmosphere; Cooling with ice; | 100% |
With periodic acid; tripropylammonium fluorochromate (VI) In acetonitrile at 0℃; for 2h; | 99% |
Conditions | Yield |
---|---|
With dmap; triethylamine In tetrahydrofuran at 20℃; for 2h; | 100% |
With dmap; triethylamine In tetrahydrofuran at 20℃; for 2h; | 100% |
C15H12ClF18NS
3-phenyl-2-propanol
bis-(4,4,5,5,6,6,7,7,7-nonafluoro-heptyl)-thiocarbamic acid O-(1-methyl-2-phenyl-ethyl) ester
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 20℃; for 12h; | 100% |
C19H12ClF26NS
3-phenyl-2-propanol
bis-(4,4,5,5,6,6,7,7,8,8,9,9,9-tridecafluoro-nonyl)-thiocarbamic acid O-(1-methyl-2-phenyl-ethyl) ester
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 20℃; for 12h; | 100% |
3-phenyl-2-propanol
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran at 20℃; for 12h; | 100% |
Conditions | Yield |
---|---|
With sodium t-butanolate In dimethyl sulfoxide at 20℃; for 3h; | 99% |
With cesium hydroxide; 4 A molecular sieve In N,N-dimethyl-formamide at 23℃; for 3h; | 90% |
Conditions | Yield |
---|---|
With pyridine; dmap In dichloromethane at 20℃; for 49h; | 99% |
Conditions | Yield |
---|---|
for 120h; | 99% |
Conditions | Yield |
---|---|
With sodium t-butanolate In dimethyl sulfoxide at 20℃; for 3h; | 99% |
Conditions | Yield |
---|---|
With sodium t-butanolate In dimethyl sulfoxide at 20℃; for 3h; | 99% |
Conditions | Yield |
---|---|
With tetra-(n-butyl)ammonium iodide; caesium carbonate In N,N-dimethyl-formamide at 23℃; for 3h; | 98% |
Stage #1: 3-phenyl-2-propanol; carbon dioxide With tetra-(n-butyl)ammonium iodide; caesium carbonate In N,N-dimethyl-formamide at 23℃; for 1h; Stage #2: benzyl chloride In N,N-dimethyl-formamide at 23℃; for 3h; | 98% |
3-phenyl-2-propanol
3-(diphenylphosphono)-2-(N-cyanoimino)thiazolidine
Conditions | Yield |
---|---|
With tert-butylmagnesium chloride In tetrahydrofuran at 20℃; for 0.25h; | 98% |
3-phenyl-2-propanol
ethenyltrimethylsilane
trimethyl[(1-phenylpropan-2-yl)oxy]silane
Conditions | Yield |
---|---|
With hydrogenchloride; chlorobis(cyclooctene)rhodium(I) dimer In 1,4-dioxane; chloroform at 20℃; for 4h; | 98% |
Wilkinson's catalyst In toluene at 100℃; for 4h; | 97% |
3-phenyl-2-propanol
p-toluenesulfonyl chloride
1-phenyl-2-propyl-4-toluenesulfonate
Conditions | Yield |
---|---|
With pyridine; dmap In dichloromethane at 20℃; for 21h; | 97% |
With pyridine Ambient temperature; | 83% |
3-phenyl-2-propanol
3-(diethylphosphono)-2-(N-cyanoimino)thiazolidine
Conditions | Yield |
---|---|
With tert-butylmagnesium chloride In tetrahydrofuran at 20℃; for 1.5h; | 97% |
3-phenyl-2-propanol
ethenyltrimethylsilane
A
ethene
B
trimethyl[(1-phenylpropan-2-yl)oxy]silane
Conditions | Yield |
---|---|
hydrogenchloride; chlorobis(cyclooctene)rhodium(I) dimer In 1,4-dioxane; chloroform for 4h; Product distribution / selectivity; | A n/a B 97% |
3-phenyl-2-propanol
4-fluorophenyl chlorothionoformate
Conditions | Yield |
---|---|
With pyridine In dichloromethane for 2h; | 96% |
Conditions | Yield |
---|---|
With tetra-(n-butyl)ammonium iodide; caesium carbonate In N,N-dimethyl-formamide at 23℃; for 5h; | 96% |
Stage #1: 3-phenyl-2-propanol; carbon dioxide With tetra-(n-butyl)ammonium iodide; caesium carbonate In N,N-dimethyl-formamide at 23℃; for 1h; Stage #2: bromoacetic acid tert-butyl ester In N,N-dimethyl-formamide at 23℃; for 5h; | 96% |
Isopropenyl acetate
3-phenyl-2-propanol
(R)-1-phenyl-2-acetoxypropane
Conditions | Yield |
---|---|
With dicarbonylchlorido(pentabenzylcyclopentadienyl)ruthenium; potassium tert-butylate; sodium carbonate In tetrahydrofuran; toluene at 23℃; for 6h; Inert atmosphere; dynamic kinetic resolution; Enzymatic reaction; optical yield given as %ee; enantioselective reaction; | 96% |
With Candida antarctica lipase B; C51H41P2Ru(1+)*C32H12BF24(1-); potassium carbonate In toluene at 20℃; for 16h; Glovebox; Enzymatic reaction; enantioselective reaction; | 95% |
With [(η5-1-methoxy-2,4-di-tert-butyl-3-neopentylcyclopentadienyl)Ru(CO)2(CO2Me)] In toluene at 25℃; for 6h; Schlenk technique; Molecular sieve; Inert atmosphere; Enzymatic reaction; enantioselective reaction; | 92% |
With air; Novozym-435; silver(l) oxide; (η5-Ph5C5)Ru(CO)(PPh3)Br In toluene at 25℃; for 20h; | 93 % Chromat. |
N-hydroxyphthalimide
3-phenyl-2-propanol
2-((1-phenylpropan-2-yl)oxy)isoindoline-1,3-dione
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran Inert atmosphere; | 96% |
With diisopropyl (E)-azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 23℃; | 68% |
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 3h; |
formic acid
3-phenyl-2-propanol
(+/-)-formic acid-(1-methyl-2-phenyl-ethyl ester)
Conditions | Yield |
---|---|
With silica triflate In hexane for 0.183333h; Heating; | 95% |
With sulfuric acid; silica gel In hexane for 0.25h; Heating; | 85% |
With magnesium hydrogen sulfate In dichloromethane for 0.5h; Heating; | 83% |
With zirconium hydrogen sulfate In hexane at 20℃; for 2h; | 75% |
With copper(II) sulfate |
3-phenyl-2-propanol
1-phenyl-2-chloropropane
Conditions | Yield |
---|---|
With oxalyl dichloride; 1-methyl-3-(2-(3-methyl-2-oxoimidazolidin-1-yl)ethyl)-1H-imidazol-3-ium hexafluorophosphate at 20 - 60℃; | 95% |
With tetrachlorosilane In tetrachloromethane at 25℃; for 0.5h; | 80% |
With gallium(III) trichloride; dimethylmonochlorosilane; diethyl (2R,3R)-tartrate In dichloromethane; pentane at 20℃; for 1h; Inert atmosphere; | 69% |
3-phenyl-2-propanol
1,1,1,3,3,3-hexamethyl-disilazane
trimethyl[(1-phenylpropan-2-yl)oxy]silane
Conditions | Yield |
---|---|
With tetrachlorosilane In dichloromethane for 0.7h; Heating; | 95% |
With potassium bromide In acetonitrile at 20℃; for 0.0833333h; | 92% |
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In acetonitrile at 20℃; | 92% |
1. | ipr-mus LD50:520 mg/kg | JPMSAE Journal of Pharmaceutical Sciences. 60 (1971),799. |
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