Magnolol
Conditions | Yield |
---|---|
With chloro-trimethyl-silane In methanol at 0 - 25℃; for 1h; | 90% |
With chloro-trimethyl-silane In methanol at 0 - 25℃; for 1h; | 90% |
With hydrogenchloride In tetrahydrofuran; isopropyl alcohol for 18h; Ambient temperature; | 70% |
2,2′-di(allyloxy)-biphenyl
Magnolol
Conditions | Yield |
---|---|
With antimonypentachloride In dichloromethane at -78℃; | 81% |
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 |
5,5'-diallyl-2,2'-dimethoxy-1,1'-biphenyl
Magnolol
Conditions | Yield |
---|---|
With boron tribromide In dichloromethane at -78℃; for 1h; | 75% |
With aluminum (III) chloride; thiourea In 1,2-dichloro-ethane at 50℃; | |
With aluminum (III) chloride; thiourea In 1,2-dichloro-ethane at 50℃; |
Conditions | Yield |
---|---|
With horseradish peroxidase type-1; dihydrogen peroxide In methanol at 20℃; for 0.3h; pH=6.0; | A 28% B 5% |
Conditions | Yield |
---|---|
With air; iron(III) chloride In ethanol for 48h; | A 15% B 2% C 1% |
Conditions | Yield |
---|---|
With sodium carbonate; potassium hexacyanoferrate(III) at 0℃; for 3h; Further byproducts given; | A 8% B 11% C 12% D 5% |
Conditions | Yield |
---|---|
With sodium carbonate; potassium hexacyanoferrate(III) at 0℃; for 3h; Further byproducts given; | A 8% B 11% C 12% D 5% |
Conditions | Yield |
---|---|
With sodium carbonate; potassium hexacyanoferrate(III) at 0℃; for 3h; Further byproducts given; | A 8% B 11% C 12% D 4% |
methyl magnesium iodide
5,5'-diallyl-2,2'-dimethoxy-1,1'-biphenyl
Magnolol
Conditions | Yield |
---|---|
at 180℃; |
methanol
1-oxaspiro[4,5]deca-6,9-dien-2,8-dione
p-cresol
A
Magnolol
B
2,2'-dihydroxy-5-methyl-5'-(2-methoxycarbonylethyl)biphenyl
Conditions | Yield |
---|---|
With sulfuric acid; tin(IV) chloride 1.) MeNO2, 2 min; 2.) reflux, 1 h; Yield given. Multistep reaction. Yields of byproduct given; |
eudesmagnolol
A
Magnolol
Conditions | Yield |
---|---|
With trifluoroacetic acid In benzene |
eudesmagnolol
A
Magnolol
B
eudesm-4-en-11-ol
Conditions | Yield |
---|---|
With trifluoroacetic acid In benzene for 10h; Ambient temperature; | A 12 mg B 3 mg |
With trifluoroacetic acid In benzene for 10h; Ambient temperature; | A 12 mg B 2 mg |
Conditions | Yield |
---|---|
With β-glucuronidase-arylsulfatase In various solvent(s) at 37℃; for 4h; Product distribution; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 95 percent / BBr3; Me2S / Heating 2: 28 percent / horseradish peroxidase type-1; aq. H2O2 / methanol / 0.3 h / 20 °C / pH 6.0 View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 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 4: 77 percent / AlCl3, DDQ / nitromethane / 1.5 h / Ambient temperature View Scheme |
p-methoxymethoxybromobenzene
Magnolol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.) Mg / 1.) THF, 2.) THF, reflux, 3 h 2: 3N aq. HCl / tetrahydrofuran / 3 h / Heating 3: 77 percent / AlCl3, DDQ / nitromethane / 1.5 h / Ambient temperature View Scheme |
1-allyl-4-(methoxymethoxy)benzene
Magnolol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 3N aq. HCl / tetrahydrofuran / 3 h / Heating 2: 77 percent / AlCl3, DDQ / nitromethane / 1.5 h / Ambient temperature View Scheme |
2,2'-dimethoxy-5,5'-dibromo-biphenyl
Magnolol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: THF / anschliessend Erwaermen mit Allylbromid 2: 180 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: bromine / chloroform / 2 h / 20 °C 2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 °C 2.2: 0 °C 3.1: ethyl bromide; magnesium / tetrahydrofuran / Inert atmosphere; Cooling with ice 3.2: 3 h / 0 - 20 °C 4.1: chloro-trimethyl-silane / methanol / 1 h / 0 - 25 °C View Scheme | |
Multi-step reaction with 4 steps 1: sodium hydroxide 2: bromine 3: tetrahydrofuran 4: thiourea; aluminum (III) chloride / 1,2-dichloro-ethane / 50 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: bromine / chloroform / 2 h 2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 °C 2.2: 0 °C 3.1: magnesium; ethyl bromide / tetrahydrofuran / 24 h / 0 - 20 °C / Inert atmosphere 3.2: 3 h / 0 - 20 °C / Inert atmosphere 4.1: chloro-trimethyl-silane / methanol / 1 h / 0 - 25 °C View Scheme |
5,5'-dibromo-2,2'-dihydroxybiphenyl
Magnolol
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 °C 1.2: 0 °C 2.1: ethyl bromide; magnesium / tetrahydrofuran / Inert atmosphere; Cooling with ice 2.2: 3 h / 0 - 20 °C 3.1: chloro-trimethyl-silane / methanol / 1 h / 0 - 25 °C View Scheme | |
Multi-step reaction with 3 steps 1.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 °C 1.2: 0 °C 2.1: magnesium; ethyl bromide / tetrahydrofuran / 24 h / 0 - 20 °C / Inert atmosphere 2.2: 3 h / 0 - 20 °C / Inert atmosphere 3.1: chloro-trimethyl-silane / methanol / 1 h / 0 - 25 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: bromine 2: tetrahydrofuran 3: thiourea; aluminum (III) chloride / 1,2-dichloro-ethane / 50 °C View Scheme |
Conditions | Yield |
---|---|
With 18-crown-6 ether; potassium carbonate In acetone for 48h; | 98% |
Magnolol
tert-butyldimethylsilyl chloride
Conditions | Yield |
---|---|
With 1H-imidazole In dichloromethane at 22℃; for 1h; Inert atmosphere; | 98% |
With 1H-imidazole In dichloromethane at 20℃; for 3h; | 96% |
Magnolol
(2S)-2-(6-methoxy(2-naphthyl))propanoic acid
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1h; | 97% |
Conditions | Yield |
---|---|
With dmap In dichloromethane at 25 - 30℃; | 97% |
Conditions | Yield |
---|---|
With 18-crown-6 ether; potassium carbonate In acetone for 17h; | 96% |
With 18-crown-6 ether; potassium carbonate In acetone for 17h; Product distribution / selectivity; |
Conditions | Yield |
---|---|
In diethyl ether for 24h; | 95% |
In diethyl ether for 24h; Product distribution / selectivity; | 95% |
In diethyl ether Ambient temperature; |
Magnolol
2',4'-difluoro-4-hydroxybiphenyl-3-carboxylic acid
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1h; | 95% |
Conditions | Yield |
---|---|
With dmap In dichloromethane at 25 - 30℃; | 95% |
Conditions | Yield |
---|---|
In 1,4-dioxane; toluene at 90℃; for 72h; | 94.5% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 22℃; for 2h; | 94% |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1h; | 93% |
With dmap In dichloromethane at 25 - 30℃; | 92% |
Magnolol
tolfenamic Acid
Conditions | Yield |
---|---|
With dmap In dichloromethane at 25 - 30℃; | 93% |
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1h; | 92% |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1h; | 92% |
With dmap In dichloromethane at 25 - 30℃; | 92% |
Magnolol
[2-(2,6-dichloroanilino)phenyl]acetic acid
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1h; | 92% |
With dmap In dichloromethane at 25 - 30℃; | 92% |
Conditions | Yield |
---|---|
Stage #1: Magnolol With potassium carbonate In acetone for 0.5h; Inert atmosphere; Reflux; Stage #2: butyryl chloride In acetone for 24h; Reflux; | A 92% B 8% |
Conditions | Yield |
---|---|
In 1,4-dioxane; toluene at 90℃; for 32h; | 91.5% |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1h; | 91% |
With dmap In dichloromethane at 25 - 30℃; | 91% |
Magnolol
ibuprofen
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1h; | 91% |
With dmap In dichloromethane at 25 - 30℃; | 91% |
Conditions | Yield |
---|---|
Stage #1: Magnolol With potassium carbonate In acetone at 20℃; for 0.166667h; Inert atmosphere; Stage #2: acetic anhydride In acetone at 20℃; for 1h; | 90% |
In pyridine |
Magnolol
etodolac
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1h; | 90% |
With dmap In dichloromethane at 25 - 30℃; | 90% |
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; sodium hydroxide In water at 80℃; for 6h; | 90% |
With sodium hydride In tetrahydrofuran; mineral oil at 60℃; for 3h; | 65% |
Magnolol
Conditions | Yield |
---|---|
With ammonium hydroxide; 10 wt% Pd(OH)2 on carbon; sodium formate; trifluoroacetic acid In m-xylene at 140℃; for 24h; Inert atmosphere; | 90% |
Conditions | Yield |
---|---|
With potassium carbonate In dimethyl sulfoxide at 40℃; for 48h; Inert atmosphere; | 90% |
Conditions | Yield |
---|---|
Stage #1: Magnolol With sodium hydride In tetrahydrofuran for 0.25h; Cooling with ice; Inert atmosphere; Stage #2: Diphenylphosphinic chloride In tetrahydrofuran at 20℃; for 3h; Inert atmosphere; Stage #3: With 3-chloro-benzenecarboperoxoic acid In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; | 89% |
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; | 88.15% |
Magnolol
ketoprofen
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 1h; | 88% |
ethyl 2-phenyldiazoacetate
Magnolol
Conditions | Yield |
---|---|
Stage #1: ethyl 2-phenyldiazoacetate; Magnolol 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; | 88% |
With sewage sludge-derived carbon material treated with perchloric acid In 1,2-dichloro-ethane at 70℃; for 24h; | 86% |
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; Solvent; Schlenk technique; | 85% |
Conditions | Yield |
---|---|
Stage #1: Magnolol With sodium hydroxide In water for 0.5h; Stage #2: 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide With tetrabutylammomium bromide In dichloromethane; water at 20℃; for 3.5h; Stage #3: Cinnamic acid Further stages; | 87.2% |
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; | 86.74% |
Molecular Structure of 5,5'-Diallyl-2,2'-biphenyldiol (CAS NO.528-43-8):
IUPAC Name: 2-(2-hydroxy-5-prop-2-enylphenyl)-4-prop-2-enylphenol
Empirical Formula: C18H18O2
Molecular Weight: 266.3343
H bond acceptors: 2
H bond donors: 2
Freely Rotating Bonds: 7
Polar Surface Area: 18.46Å2
Index of Refraction: 1.601
Molar Refractivity: 82.42 cm3
Molar Volume: 240.4 cm3
Surface Tension: 44.6 dyne/cm
Density: 1.107 g/cm3
Flash Point: 184.5 °C
Enthalpy of Vaporization: 67.74 kJ/mol
Boiling Point: 401 °C at 760 mmHg
Vapour Pressure: 5.25E-07 mmHg at 25°C
Storage temp: 2-8°C
Merck: 13,5721
InChI
InChI=1/C18H18O2/c1-3-5-13-7-9-17(19)15(11-13)16-12-14(6-4-2)8-10-18(16)20/h3-4,7-12,19-20H,1-2,5-6H2
Smiles
c1(c2c(ccc(c2)CC=C)O)c(ccc(c1)CC=C)O
Product Categories: Aromatic Phenols; The group of Magnolia; Antifungal; Nutritional Ingredients
1. | orl-mus LD50:2200 mg/kg | BRXXAA British Patent Document. (U.S. Patent Office, Science Library, 2021 Jefferson Davis Highway, Arlington, VA 22202) #5135746 . |
Moderately toxic by ingestion. When heated to decomposition it emits acrid smoke and irritating vapors.
Hazard Codes: N
Risk Statements: 37/38-41-51/53
R37/38:Irritating to respiratory system and skin.
R41:Risk of serious damage to the eyes.
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements: 26-39-61
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S39:Wear eye / face protection.
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
RIDADR: UN 3077
RTECS: DV5105500
5,5'-Diallyl-2,2'-biphenyldiol , with CAS number of 528-43-8, can be called 2,2'-Bichavicol(6CI) ; [1,1'-Biphenyl]-2,2'-diol,5,5'-di-2-propenyl- (9CI) ; 2,2'-Biphenyldiol, 5,5'-diallyl- (8CI) . 5,5'-Diallyl-2,2'-biphenyldiol (CAS NO.528-43-8) can be used in Pharmacological.
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