Conditions | Yield |
---|---|
With ammonium formate; palladium on activated charcoal In tetrahydrofuran; methanol at 20℃; for 0.55h; | 99% |
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; silica gel In benzene at 70℃; for 4h; | 95% |
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate In benzene at 70℃; Rate constant; Product distribution; further reaction conditions; deuterium isotopic effect; | |
With hydrogen; palladium on activated charcoal In tetrahydrofuran Ambient temperature; | |
With hydrogen; palladium on activated charcoal In ethyl acetate for 1h; |
Conditions | Yield |
---|---|
With palladium 10% on activated carbon; hydrogen In dichloromethane at 20℃; under 760.051 Torr; for 6h; Catalytic behavior; Time; | 98% |
With 10% Pd/C; diphenyl sulfide; hydrogen In methanol at 20℃; for 24h; chemoselective reaction; | 97% |
With palladium 10% on activated carbon; hydrogen In ethanol under 1875.19 Torr; for 0.5h; | 95% |
phenethylmagnesium chloride
salicylic acid
2'-hydroxy-3-phenylpropiophenone
Conditions | Yield |
---|---|
Stage #1: salicylic acid With tert-butylmagnesium chloride In tetrahydrofuran; toluene at 0℃; for 0.25h; Inert atmosphere; Stage #2: phenethylmagnesium chloride With diisopropylaminomagnesium chloride lithium chloride In tetrahydrofuran; toluene at 0 - 20℃; for 14.25h; Inert atmosphere; Sonication; | 98% |
2'-hydroxy-3-phenylpropiophenone
Conditions | Yield |
---|---|
With acetic acid In tetrahydrofuran; water at 40℃; for 4h; | 89% |
1-(2'-hydroxyphenyl)prop-2-en-1-ol
phenylboronic acid
2'-hydroxy-3-phenylpropiophenone
Conditions | Yield |
---|---|
With 2.9-dimethyl-1,10-phenanthroline; palladium diacetate; copper(l) chloride In dimethyl sulfoxide at 50℃; under 760.051 Torr; for 12h; | 89% |
With 2.9-dimethyl-1,10-phenanthroline; palladium diacetate; silver carbonate In acetonitrile at 60℃; for 24h; regioselective reaction; | 85% |
styrene
salicylaldehyde
A
2'-hydroxy-3-phenylpropiophenone
B
1-(2-Hydroxyphenyl)-2-phenylpropan-1-one
Conditions | Yield |
---|---|
With potassium phosphate; chloro(1,5-cyclooctadiene)rhodium(I) dimer; (11aR)-(+)-10,11,12,13-tetrahydrodiindeno[7,1-de:1', 7'-fg][1,3,2]dioxaphosphocin-5-bis[(R)-1-phenylethyl]amine In 1,2-dichloro-ethane at 70℃; for 36h; Inert atmosphere; Overall yield = 98 %; | A 87% B n/a |
Conditions | Yield |
---|---|
With aluminium trichloride for 1h; | 84% |
With aluminum (III) chloride at 100℃; for 1h; Fries Phenol Ester Rearrangement; |
Conditions | Yield |
---|---|
With lithium tert-butoxide In toluene at 110℃; for 12h; Inert atmosphere; | 84% |
With C61H47N3OP2Ru; potassium hydroxide In toluene at 110℃; for 12h; | 80% |
With C51H39As2N3O2RuS; sodium hydroxide In toluene at 105℃; for 8h; | 79% |
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; potassium hydroxide In tert-Amyl alcohol at 110℃; for 24h; Sealed tube; | 50% |
phenyl 3-phenylpropanoate
A
2'-hydroxy-3-phenylpropiophenone
B
1-(4-hydroxyphenyl)-3-phenylpropan-1-one
Conditions | Yield |
---|---|
With methanesulfonic acid; Methanesulfonic anhydride at 65℃; Fries rearrangement; Inert atmosphere; regioselective reaction; | A n/a B 82% |
phenyl Salicylate
1-phenyl-2-bromoethane
2'-hydroxy-3-phenylpropiophenone
Conditions | Yield |
---|---|
With 1,10-Phenanthroline; nickel(II) bromide diethylene glycol dimethyl ether; zinc In N,N-dimethyl-formamide at 60℃; for 10h; Inert atmosphere; Sealed tube; | 71% |
Conditions | Yield |
---|---|
Stage #1: o-hydroxyacetophenone; benzaldehyde With sodium hydride In N,N-dimethyl-formamide at 20℃; Stage #2: With palladium 10% on activated carbon; hydrogen In tetrahydrofuran at 20℃; | 68% |
With potassium hydroxide; tris(triphenylphosphine)ruthenium(II) chloride In 1,4-dioxane at 80℃; for 40h; | 49% |
With sodium hydroxide; hydrogen; palladium on activated charcoal 1.) methanol, r.t., 60 h, 2.) methanol, normal pressure; Yield given. Multistep reaction; | |
Multistep reaction; |
A
2'-hydroxy-3-phenylpropiophenone
B
N-methyl-N-phenyl-3-phenylpropanamide
C
salicylic acid
Conditions | Yield |
---|---|
With water; sodium hydride In tetrahydrofuran for 24h; Reflux; | A n/a B 42% C 42% |
2-(5-phenyl-4,5-dihydroisoxazol-3-yl)phenol
A
2'-hydroxy-3-phenylpropiophenone
B
3-hydroxy-1-(2-hydroxyphenyl)-3-phenylpropan-1-one
Conditions | Yield |
---|---|
With hydrogen; boric acid; nickel In methanol; water | A 14% B 38% |
(Z)-1-acetoxy-1-(2-acetoxyphenyl)-3-phenylpropene
A
2'-hydroxy-3-phenylpropiophenone
B
2-methyl-3-(phenylmethyl)chromone
C
1-(2-acetoxyphenyl)-3-phenyl-1-propane
D
1-(2-acetoxyphenyl)-3-phenyl-1,4-pentanedione
Conditions | Yield |
---|---|
In hexane for 6h; Irradiation; | A 6% B 24% C 32% D 16% |
In hexane for 6h; Mechanism; Irradiation; | A 6% B 24% C 32% D 16% |
In hexane for 2h; Ambient temperature; Irradiation; | A 30% B 24% C 6% D 16% |
Conditions | Yield |
---|---|
With Penicillium raistrickii CBMAI 931 In aq. phosphate buffer at 32℃; for 168h; pH=7; | 30% |
With sodium hydroxide; palladium on activated charcoal Hydrogenation; | |
With hydrogen; palladium |
Conditions | Yield |
---|---|
With Rhodococcus sp. DSM 364 In acetone at 28℃; for 168h; Microbiological reaction; | A 30% B 13% |
Flavanone
A
2'-hydroxy-3-phenylpropiophenone
B
1-(2'-hydroxyphenyl)-3-(4-hydroxyphenyl)propan-1-one
Conditions | Yield |
---|---|
With Fusarium sp. CBMAI 1830 at 32℃; for 168h; | A 6% B 30% |
Conditions | Yield |
---|---|
at 110℃; for 0.5h; Condensation; | A n/a B 29% |
1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one
A
2'-hydroxy-3-phenylpropiophenone
B
1-(2'-hydroxyphenyl)-3-(4-hydroxyphenyl)propan-1-one
Conditions | Yield |
---|---|
With Aspergillus sydowii CBMAI 935 In aq. phosphate buffer; dimethyl sulfoxide at 32℃; for 168h; pH=7; Microbiological reaction; chemoselective reaction; | A n/a B 26% |
Multi-step reaction with 2 steps 1: potassium hydroxide; L-proline / water / 20 °C 2: Fusarium sp. CBMAI 1830 / 168 h / 32 °C View Scheme |
Conditions | Yield |
---|---|
With sodium hydroxide; palladium on activated charcoal Hydrogenation; |
1-(2-methoxyphenyl)-3-phenylpropan-1-one
2'-hydroxy-3-phenylpropiophenone
Conditions | Yield |
---|---|
With boron trichloride In chloroform |
o-hydroxyacetophenone
benzyl chloride
A
2'-hydroxy-3-phenylpropiophenone
B
2-benzyl-1-(2-hydroxyphenyl)-3-phenylpropan-1-one
Conditions | Yield |
---|---|
With lithium diisopropyl amide 1.) THF, 0 deg C to 25 deg C, 1 h, 2.) THF, -50 deg C to 25 deg C; Yield given. Multistep reaction. Yields of byproduct given; |
2'-hydroxy-3-phenylpropiophenone
Conditions | Yield |
---|---|
With acetic acid; platinum Hydrogenation; |
2-(1-isopropyliminoethyl) phenol
2'-hydroxy-3-phenylpropiophenone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) LDA / 1.) THF, 0 deg C to 25 deg C, 1 h, 2.) THF, -50 deg C to 25 deg C 2: 89 percent / AcOH / tetrahydrofuran; H2O / 4 h / 40 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) LDA / 1.) THF, 0 deg C to 25 deg C, 1 h, 2.) THF, -50 deg C to 25 deg C 2: 89 percent / AcOH / tetrahydrofuran; H2O / 4 h / 40 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 54 percent / N-chlorosuccinimide, pyridine / CHCl3 / 2 h / Heating 2: 14 percent / H2, boric acid / Raney-Ni / methanol; H2O View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 54 percent / N-chlorosuccinimide, pyridine / CHCl3 / 2 h / Heating 2: 14 percent / H2, boric acid / Raney-Ni / methanol; H2O View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 57 percent / KOH / ethanol; H2O / 10 h / Ambient temperature 2: 801 mg / H2 / Adams catalyst / ethyl acetate / 0.17 h / 2068.6 Torr / Ambient temperature View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 57 percent / KOH / ethanol; H2O / 10 h / Ambient temperature 2: 801 mg / H2 / Adams catalyst / ethyl acetate / 0.17 h / 2068.6 Torr / Ambient temperature View Scheme |
2'-hydroxy-3-phenylpropiophenone
1-(2-hydroxyphenyl)-3-phenyl-1-propanol
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol | 99% |
With lithium aluminium tetrahydride In diethyl ether for 17h; Heating; | 94% |
With sodium tetrahydroborate In methanol Reduction; | 89% |
2'-hydroxy-3-phenylpropiophenone
epichlorohydrin
1-(2-(oxiran-2-ylmethoxy)phenyl)-3-phenylpropan-1-one
Conditions | Yield |
---|---|
With sodium hydroxide for 18h; Reflux; | 99% |
With sodium hydroxide for 12h; Heating; | 90.6% |
for 4h; Reflux; | 82% |
2'-hydroxy-3-phenylpropiophenone
ethylene glycol
2-(2-phenethyl-1,3-dioxolan-2-yl)phenol
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid; trimethyl orthoformate In hexane at 40℃; for 72h; | 99% |
With toluene-4-sulfonic acid In benzene for 86h; Heating; | 62.8% |
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 16h; | 99% |
2'-hydroxy-3-phenylpropiophenone
chloroacetic acid ethyl ester
2-(2-(3-phenylpropionyl)-phenoxy)-essigsaeureethylester
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 24h; Heating; | 96% |
With potassium carbonate In acetone for 24h; Heating; | 72% |
Conditions | Yield |
---|---|
With potassium phosphate; tetrabutylammomium bromide In water at 20℃; for 2h; | 95% |
With potassium carbonate; potassium iodide In acetone at 50℃; for 11h; | 80% |
2'-hydroxy-3-phenylpropiophenone
N,N-dimethyl-formamide dimethyl acetal
3-benzyl-4H-1-benzopyran-4-one
Conditions | Yield |
---|---|
In toluene for 5h; Heating; | 94% |
Conditions | Yield |
---|---|
With [(C6H6)(PCy3)(CO)RuH]+*BF4−; hydrogen; phenol In 1,4-dioxane; isopropyl alcohol at 130℃; under 1520.1 Torr; for 8h; Inert atmosphere; Glovebox; Schlenk technique; chemoselective reaction; | 92% |
Conditions | Yield |
---|---|
With bismuth(III) chloride; silver(I) bromide; magnesium; copper(ll) bromide In tetrahydrofuran; toluene at 96℃; for 12h; chemoselective reaction; | 92% |
2-bromophenylacetic acid
2'-hydroxy-3-phenylpropiophenone
phenylacetic acid
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran Heating; | 91% |
Conditions | Yield |
---|---|
With bismuth(III) chloride; silver(I) bromide; magnesium; copper(ll) bromide In tetrahydrofuran; toluene at 96℃; for 12h; chemoselective reaction; | 91% |
Conditions | Yield |
---|---|
With oxygen; palladium diacetate; trifluoroacetic acid In dimethyl sulfoxide at 80℃; for 9h; Sealed tube; | 91% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 50℃; for 96h; | 88% |
1-bromomethyl-1,2-dicarba-closo-dodecaborane(12)
2'-hydroxy-3-phenylpropiophenone
Conditions | Yield |
---|---|
With 3-dodecyl-1,2-dimethyl-1H-imidazol-3-ium tetrafluoroborate; triethylamine at 60 - 70℃; for 6h; Reagent/catalyst; Temperature; | 84% |
Conditions | Yield |
---|---|
With palladium(II) trifluoroacetate; 5-Nitro-1,10-phenanthroline; oxygen In dimethyl sulfoxide at 100℃; for 48h; Catalytic behavior; Reagent/catalyst; | 81% |
Conditions | Yield |
---|---|
With bismuth(III) chloride; silver(I) bromide; magnesium; copper(ll) bromide In tetrahydrofuran; toluene at 96℃; for 12h; chemoselective reaction; | 80% |
With silver(I) bromide; bismuth(III) chloride; magnesium; copper(ll) bromide In tetrahydrofuran; toluene at 96℃; for 12h; |
Conditions | Yield |
---|---|
With bismuth(III) chloride; silver(I) bromide; magnesium; copper(ll) bromide In tetrahydrofuran; toluene at 96℃; for 12h; chemoselective reaction; | 80% |
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; potassium carbonate In water; toluene for 144h; Reflux; | 79% |
2'-hydroxy-3-phenylpropiophenone
A
FLAVONE
B
Flavanone
C
1-(2-hydroxyphenyl)-3-phenylprop-2-en-1-one
Conditions | Yield |
---|---|
Stage #1: 2'-hydroxy-3-phenylpropiophenone With palladium(II) trifluoroacetate; copper diacetate In dimethyl sulfoxide at 100℃; for 15h; Inert atmosphere; Stage #2: With hydrogenchloride In water; dimethyl sulfoxide; ethyl acetate at 100℃; for 24h; Reagent/catalyst; Inert atmosphere; | A 10% B 79% C 8% |
Conditions | Yield |
---|---|
With bismuth(III) chloride; silver(I) bromide; magnesium; copper(ll) bromide In tetrahydrofuran; toluene at 96℃; for 12h; chemoselective reaction; | 78% |
chloroacetaldehyde dimethyl acetal
2'-hydroxy-3-phenylpropiophenone
1-(2-(2,2-Dimethoxyethoxy)phenyl)-3-phenyl-1-propanon
Conditions | Yield |
---|---|
With sodium hydroxide; potassium iodide for 24h; Heating; | 77% |
IUPAC Name: 1-(2-Hydroxyphenyl)-3-phenylpropan-1-one
Systematic of 1-Propanone,1-(2-hydroxyphenyl)-3-phenyl- (CAS NO.3516-95-8): EINECS 222-521-4 ; 1-(2-Hydroxyphenyl)-3-phenylpropan-1-one
CAS NO: 3516-95-8
Molecular Formula of 1-Propanone,1-(2-hydroxyphenyl)-3-phenyl- (CAS NO.3516-95-8): C15H14O2
Molecular Weight: 226.2705
Molecular Structure:
Melting Point: 36-37 °C
H bond acceptors: 2
H bond donors: 1
Freely Rotating Bonds: 5
Polar Surface Area: 26.3 Å2
Index of Refraction: 1.6
Molar Refractivity: 67.28 cm3
Molar Volume: 196.6 cm3
Surface Tension: 48.7 dyne/cm
Density of 1-Propanone,1-(2-hydroxyphenyl)-3-phenyl- (CAS NO.3516-95-8): 1.15 g/cm3
Flash Point: 162.7 °C
Enthalpy of Vaporization: 65.39 kJ/mol
Boiling Point: 381.1 °C at 760 mmHg
Vapour Pressure: 2.38E-06 mmHg at 25°C
1-Propanone,1-(2-hydroxyphenyl)-3-phenyl- (CAS NO.3516-95-8) is used as oyster preservatives.
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S37/39: Wear suitable gloves and eye/face protection.
WGK Germany: 3
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