Conditions | Yield |
---|---|
With aluminium(III) iodide; diisopropyl-carbodiimide In acetonitrile at 80℃; for 18h; | 100% |
With boron tribromide In dichloromethane at 0℃; for 1h; Inert atmosphere; | 97.5% |
With dimethylsulfide; boron tribromide Heating; | 95% |
Conditions | Yield |
---|---|
With caesium carbonate In 2,2,2-trifluoroethanol for 14h; Irradiation; | 87% |
With caesium carbonate In 2,2,2-trifluoroethanol for 4h; Irradiation; Flow reactor; | 70% |
4-[3-(2-Nitro-phenylselanyl)-propyl]-phenol
4-(prop-2-enyl)phenol
Conditions | Yield |
---|---|
With dihydrogen peroxide In tetrahydrofuran at 40℃; for 3.5h; | 80% |
Conditions | Yield |
---|---|
Stage #1: p-ethoxyallylbenzene With aluminum (III) chloride; N,N-dimethyl-aniline In toluene at 100 - 110℃; for 2 - 3h; Stage #2: With hydrogenchloride; water In toluene at 20℃; pH=1 - 2; Product distribution / selectivity; | 80% |
Conditions | Yield |
---|---|
Stage #1: p-Iodophenol With dilithium tetra(tert-butyl)zincate In tetrahydrofuran at 40℃; for 2h; Stage #2: allyl bromide In tetrahydrofuran at 20℃; for 12h; | 79% |
Stage #1: p-Iodophenol With dilithium tetra(tert-butyl)zincate In tetrahydrofuran at -78 - 40℃; Inert atmosphere; Stage #2: allyl bromide In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; chemoselective reaction; | 79% |
Conditions | Yield |
---|---|
With potassium carbonate In water at 135℃; for 0.3h; Suzuki-Miyaura Coupling; Microwave irradiation; Sealed tube; | 75% |
4-chloro-phenol
allyl-trimethyl-silane
A
4-(prop-2-enyl)phenol
B
phenol
Conditions | Yield |
---|---|
In water; acetonitrile for 2.5h; Concentration; Irradiation; Flow reactor; | A 75% B 7 %Chromat. |
Conditions | Yield |
---|---|
{(norbornadiene)rhodium(I)(NCCH3)2}(PF6) In toluene at 0℃; for 24h; | 54% |
Conditions | Yield |
---|---|
Stage #1: Estragole With boron tribromide In dichloromethane at 0 - 20℃; for 3.75h; Inert atmosphere; Stage #2: With water In dichloromethane Inert atmosphere; | A 49% B 31% |
2-(4-(allyloxy)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
4-(prop-2-enyl)phenol
Conditions | Yield |
---|---|
With C14H16N6; palladium diacetate; calcium hydroxide In N,N-dimethyl acetamide; water at 70℃; for 48h; Inert atmosphere; | 43% |
allyl (p-tolyl)sulfide
4-diazo-2,5-cyclohexadienone
A
4-(prop-2-enyl)phenol
Conditions | Yield |
---|---|
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} In 1,2-dichloro-ethane at 40℃; Inert atmosphere; Molecular sieve; Schlenk technique; chemoselective reaction; | A 41% B 32% |
allyl phenyl ether
A
4-(prop-2-enyl)phenol
B
2-Allylphenol
C
phenol
Conditions | Yield |
---|---|
With β‐cyclodextrin In water at 25℃; for 0.5h; Irradiation; | A 21.9% B 40.2% C 2.1% |
With β‐cyclodextrin In water at 25℃; for 0.5h; Quantum yield; Irradiation; without β-CD, in nitrogen or oxygen atmosphere; | A 21.9% B 40.2% C 2.1% |
In methanol Product distribution; Kinetics; Quantum yield; Further Variations:; Solvents; Reagents; photo-Claisen rearrangement; Irradiation; | |
In butan-1-ol at 35℃; for 0.0833333h; Temperature; Time; Concentration; Claisen Rearrangement; Flow reactor; UV-irradiation; |
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at 25℃; | A 38% B 8% |
Conditions | Yield |
---|---|
With KU-2-8 cation-exchange resin at 95 - 97℃; for 4h; | 10% |
Conditions | Yield |
---|---|
at 160 - 170℃; |
Conditions | Yield |
---|---|
With ethanol; ammonia; sodium |
4-(2-propenyl)aniline
4-(prop-2-enyl)phenol
Conditions | Yield |
---|---|
With sulfuric acid; sodium nitrite anschliessendes Erwaermen; |
4-(prop-2-enyl)phenol
Conditions | Yield |
---|---|
With diethyl ether; oxygen |
Conditions | Yield |
---|---|
Irradiation.UV-Licht; |
allyl phenyl ether
isopropyl alcohol
A
4-(prop-2-enyl)phenol
B
phenol
Conditions | Yield |
---|---|
UV-Licht.Irradiation; |
allyl bromide
phenol
A
4-(prop-2-enyl)phenol
B
2,4-di(prop-2-en-1-yl)phenol
C
2-Allylphenol
Conditions | Yield |
---|---|
With sodium hydroxide In water |
(2-Allyl-phenoxy)-trimethyl-silan
4-(prop-2-enyl)phenol
Conditions | Yield |
---|---|
With acid In methanol Yield given; |
methanol
acetic anhydride
miyaginin
A
4-(prop-2-enyl)phenol
B
methyl 2,3,4-tri-O-acetyl-α-D-xylopyranoside
C
Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-4-yl ester
Conditions | Yield |
---|---|
With pyridine; sulfuric acid 1) reflux, 14 h, 2) room temperature, 14 h; Yield given. Multistep reaction. Yields of byproduct given; |
dimethylovobatol
A
4-(prop-2-enyl)phenol
B
4-propyl-1,2-dimethoxybenzene
Conditions | Yield |
---|---|
With potassium In ammonia at -70 - -62℃; for 1.5h; |
A
2,3,4-tri-O-methyl-D-glucopyranose
B
4-(prop-2-enyl)phenol
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol for 2h; Heating; Yield given; |
1-allyl-4-(methoxymethoxy)benzene
4-(prop-2-enyl)phenol
Conditions | Yield |
---|---|
With sulfuric acid; acetic acid | |
With hydrogenchloride In tetrahydrofuran for 3h; Heating; Yield given; |
Conditions | Yield |
---|---|
Erhitzen des Reaktionsprodukts bei 10-15 mm Druck auf 150-160grad; |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 98 percent / K2CO3 / acetone / 2 h / Heating 2: 1.) Mg / 1.) THF, 2.) THF, reflux, 3 h 3: 3N aq. HCl / tetrahydrofuran / 3 h / Heating View Scheme |
p-methoxymethoxybromobenzene
4-(prop-2-enyl)phenol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) Mg / 1.) THF, 2.) THF, reflux, 3 h 2: 3N aq. HCl / tetrahydrofuran / 3 h / Heating View Scheme |
4-(prop-2-enyl)phenol
tert-butyldimethylsilyl chloride
Conditions | Yield |
---|---|
With 1H-imidazole In dichloromethane at 0 - 20℃; Inert atmosphere; | 98% |
With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; | 96% |
4-(prop-2-enyl)phenol
isobutene
1-(tert-butoxy)-4-(prop-2-enyl)benzene
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid In dichloromethane at -78℃; for 3h; | 96% |
4-(prop-2-enyl)phenol
benzyl bromide
1-(benzyloxy)-4-(prop-2-en-1-yl)benzene
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 4h; Reflux; | 95% |
ethyl 2-phenyldiazoacetate
4-(prop-2-enyl)phenol
Conditions | Yield |
---|---|
Stage #1: ethyl 2-phenyldiazoacetate; 4-(prop-2-enyl)phenol In 1,2-dichloro-ethane at 20℃; for 0.0333333h; Schlenk technique; Green chemistry; Stage #2: With trifluorormethanesulfonic acid In 1,2-dichloro-ethane for 0.333333h; Schlenk technique; Green chemistry; | 90% |
With sewage sludge-derived carbonaceous materials treated by perchloric acid; air In 1,2-dichloro-ethane at 20 - 70℃; under 750.075 Torr; for 5h; Schlenk technique; | 72% |
4-(prop-2-enyl)phenol
chloromethyl methyl ether
1-allyl-4-(methoxymethoxy)benzene
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran 1.) r.t., 1 h, 2.) r.t., 12 h; | 89% |
4-(prop-2-enyl)phenol
acetic anhydride
phenol, 4-(2-propenyl)-, acetate
Conditions | Yield |
---|---|
With pyridine at 20℃; for 16h; | 89% |
With dmap; triethylamine In dichloromethane at 20℃; for 0.333333h; | 71% |
With triethylamine In dichloromethane |
4-(prop-2-enyl)phenol
Conditions | Yield |
---|---|
With Grubbs catalyst first generation In dichloromethane for 4.5h; Inert atmosphere; Reflux; | 87.3% |
Conditions | Yield |
---|---|
With iron(III) chloride; tetramethyldisiloxane In ethanol at 20℃; for 24h; | 86% |
Conditions | Yield |
---|---|
With tris(pentafluorophenyl)borate In toluene at 25℃; for 0.5h; chemoselective reaction; | 84% |
Conditions | Yield |
---|---|
With tris(pentafluorophenyl)borate In toluene at 25℃; for 0.5h; Inert atmosphere; Sealed tube; | 84% |
4-(prop-2-enyl)phenol
(S)-Glycidyl tosylate
(S)-2-((4-allylphenoxy)methyl)oxirane
Conditions | Yield |
---|---|
Stage #1: 4-(prop-2-enyl)phenol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h; Stage #2: (S)-Glycidyl tosylate In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; | 79% |
Conditions | Yield |
---|---|
With dmap In dichloromethane at 0 - 23℃; for 6h; Inert atmosphere; | 78% |
With dmap In dichloromethane at 0 - 23℃; for 6h; Inert atmosphere; | 78% |
With dmap In dichloromethane at 0 - 23℃; for 6h; Inert atmosphere; | 78% |
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere; | 78% |
Conditions | Yield |
---|---|
With aluminium trichloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone In nitromethane for 1.5h; Ambient temperature; | 77% |
With air; ethanol; iron(III) chloride |
4-(prop-2-enyl)phenol
isopentanoyl chloride
4-allylphenyl 3-methylbutanoate
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere; | 75% |
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere; | 73% |
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere; | 70% |
With sodium hydroxide | |
Stage #1: 4-(prop-2-enyl)phenol With sodium hydroxide In water Stage #2: benzoyl chloride In water for 0.5h; | 0.32 g |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 5h; Inert atmosphere; | 66% |
4-(prop-2-enyl)phenol
4-fluorobenzaldehyde
4-(4-allyl phenoxy)benzaldehyde
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 48h; | 63% |
4-(prop-2-enyl)phenol
Conditions | Yield |
---|---|
With N-Bromosuccinimide; tert-butylamine In dichloromethane at 0℃; for 1h; | 61% |
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In chloroform at 20℃; for 2.08333h; | 50.6% |
Conditions | Yield |
---|---|
Stage #1: 4-(prop-2-enyl)phenol With (Z)-2-Butene; C33H28Cl2F2N2ORuS2 In tetrahydrofuran at 22℃; for 1h; Cross Metathesis; Inert atmosphere; Stage #2: (Z)-but-2-enamide In tetrahydrofuran at 22℃; for 20h; Cross Metathesis; Inert atmosphere; diastereoselective reaction; | 61% |
[bis(acetoxy)iodo]benzene
4-(prop-2-enyl)phenol
1-allyl-4-oxocyclohexa-2,5-dienylethanoate
Conditions | Yield |
---|---|
In acetic acid for 8h; | 60% |
4-(prop-2-enyl)phenol
benzyl (Z)-but-2-enoate
Conditions | Yield |
---|---|
Stage #1: 4-(prop-2-enyl)phenol With (Z)-2-Butene; C33H28Cl2F2N2ORuS2 In tetrahydrofuran at 22℃; for 1h; Cross Metathesis; Inert atmosphere; Stage #2: benzyl (Z)-but-2-enoate In tetrahydrofuran at 22℃; for 20h; Cross Metathesis; Inert atmosphere; diastereoselective reaction; | 59% |
The Phenol,4-(2-propen-1-yl)-, with the CAS registry number 501-92-8 and EINECS registry number 207-929-2, has the systematic name of 4-allylphenol, and the IUPAC name of 4-prop-2-enylphenol. The molecular formula of the chemical is C9H10O.
The characteristics of Phenol,4-(2-propen-1-yl)- are as followings: (1)ACD/LogP: 2.50; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.5; (4)ACD/LogD (pH 7.4): 2.5 ; (5)#H bond acceptors: 1; (6)#H bond donors: 1; (7)#Freely Rotating Bonds: 3; (8)Polar Surface Area: 20.23 Å2; (9)Index of Refraction: 1.548; (10)Molar Refractivity: 42.04 cm3; (11)Molar Volume: 132.2 cm3; (12)Polarizability: 16.66×10-24cm3; (13)Surface Tension: 37.6 dyne/cm; (14)Density: 1.014 g/cm3; (15)Flash Point: 102.6 °C; (16)Enthalpy of Vaporization: 49.41 kJ/mol; (17)Boiling Point: 238 °C at 760 mmHg; (18)Vapour Pressure: 0.0282 mmHg at 25°C.
Uses of Phenol,4-(2-propen-1-yl)-: It can react with 2-methyl-propene to produce 1-allyl-4-tert-butoxy-benzene. This reaction will need reagent CF3SO3H, and the menstruum CH2Cl2. The reaction time is 3 hours with temperature of -78°C, and the yield is about 96%.
Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: Oc1ccc(CC=C)cc1
(2)InChI: InChI=1/C9H10O/c1-2-3-8-4-6-9(10)7-5-8/h2,4-7,10H,1,3H2
(3)InChIKey: RGIBXDHONMXTLI-UHFFFAOYAI
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