Conditions | Yield |
---|---|
With copper acetylacetonate; N1-(4-hydroxy-2,6-dimethylphenyl)-N2-(4-hydroxy-3,5-dimethylphenyl)oxalamide; potassium hydroxide In water; dimethyl sulfoxide at 60℃; for 24h; Schlenk technique; Inert atmosphere; | 99% |
With copper(I) oxide; 1D-1-O-Methyl-muco-inostol; sodium hydroxide In water at 130℃; for 6h; | 59% |
With formic acid; oxygen; triethylamine; copper(ll) bromide In acetonitrile at 20℃; for 48h; Irradiation; | 52% |
Conditions | Yield |
---|---|
With copper acetylacetonate; N1-(4-hydroxy-2,6-dimethylphenyl)-N2-(4-hydroxy-3,5-dimethylphenyl)oxalamide; water In water; dimethyl sulfoxide at 80℃; for 24h; Schlenk technique; Inert atmosphere; | 99% |
With tris(6,6'-diamino-2,2'-bipyridine); 4,4-diphenyl-1,3,5,7,8-pentamethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene; Br2Ni*3H2O; water; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide; acetonitrile at 120℃; for 24h; Glovebox; Irradiation; Inert atmosphere; | 72% |
Stage #1: 1,2-(methylenedioxy)-4-bromobenzene With magnesium In tetrahydrofuran Inert atmosphere; Stage #2: With oxaziridine In tetrahydrofuran at 0 - 25℃; for 2h; Inert atmosphere; Stage #3: With ammonium chloride In tetrahydrofuran; water Inert atmosphere; | 63% |
Conditions | Yield |
---|---|
Stage #1: piperonal With 3-chloro-benzenecarboperoxoic acid for 0.0833333h; Dakin oxidation; Stage #2: With sodium hydroxide for 0.0833333h; Further stages.; | 95% |
With sulfuric acid; dihydrogen peroxide; boric acid In tetrahydrofuran; water at 20℃; for 3.5h; Oxidation; | 89% |
With sulfuric acid; dihydrogen peroxide; boric acid; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 0℃; Dakin reaction; | 78% |
benzo[d][1,3]dioxol-5-yl 4-methylbenzenesulfonate
Sesamol
Conditions | Yield |
---|---|
With magnesium In methanol for 4h; Ambient temperature; | 95% |
With potassium fluoride on basic alumina for 0.05h; Substitution; microwave irradiation; | 88% |
With (2’,4’,6’-triisopropyl-[1,1’-biphenyl]-2-yl)-diphenylphosphine; bis(2-phenylpyridinato)(2,2'-bipyridine)iridium(III) hexafluorophosphate; carbon dioxide; tetrabutylammomium bromide; palladium diacetate; caesium carbonate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 20℃; under 760.051 Torr; for 4h; Irradiation; | 31% |
Conditions | Yield |
---|---|
With water; potassium hydroxide In methanol at 50℃; for 2h; | 95% |
With water at 20℃; for 1.25h; | 95% |
Sesamol
Conditions | Yield |
---|---|
With hydrogenchloride In water pH=8.5; | 94.3% |
5-(2-Methoxy-ethoxymethoxy)-benzo[1,3]dioxole
Sesamol
Conditions | Yield |
---|---|
With 2-chloro-1,3,2-dithioborolane In dichloromethane at -78℃; for 0.75h; | 94% |
5-propionyloxy-benzo[1,3]dioxole
Sesamol
Conditions | Yield |
---|---|
Stage #1: 5-propionyloxy-benzo[1,3]dioxole With sodium hydroxide; tetrabutyl-ammonium chloride; water In dichloromethane at 20 - 25℃; for 8 - 8.75h; Stage #2: With hydrogenchloride In dichloromethane; water pH=8.5; | 92.3% |
3,4-(methylenedioxy)-benzeneboronic acid
Sesamol
Conditions | Yield |
---|---|
With 2,5-dimethylfuran; zinc(II) phthalocyanine; oxygen In tetrahydrofuran at 25℃; under 760.051 Torr; for 1.5h; Irradiation; Sealed tube; Schlenk technique; | 92% |
With dihydrogen peroxide In water at 20℃; for 0.0833333h; | 92% |
With oxygen; triethylamine In 2-methyltetrahydrofuran at 20℃; under 760.051 Torr; for 24h; Green chemistry; | 88% |
With rongalite In ethanol; water at 20℃; for 7h; Irradiation; | 71% |
With [Rh2(bpy)2(μ-OAc)2(OAc)2]; oxygen; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide under 760.051 Torr; for 18h; Irradiation; | 30 mg |
Sesamol
Conditions | Yield |
---|---|
With carbon tetrabromide In methanol for 5h; ether cleavage; Heating; | 91% |
Conditions | Yield |
---|---|
With copper acetylacetonate; N1-(4-hydroxy-2,6-dimethylphenyl)-N2-(4-hydroxy-3,5-dimethylphenyl)oxalamide; water In water; dimethyl sulfoxide at 130℃; for 24h; Schlenk technique; Inert atmosphere; | 88% |
With trans-di(μ-acetato)bis[o-(di-o-tolyl-phosphino)benzyl]dipalladium(II); C29H45Pt; caesium carbonate In water; N,N-dimethyl-formamide at 130℃; for 0.5h; Inert atmosphere; Microwave irradiation; | 51% |
Sesamol
Conditions | Yield |
---|---|
With methanol; sodium tetrahydroborate; nickel(II) chloride hexahydrate at 20℃; for 0.25h; chemoselective reaction; | 88% |
Conditions | Yield |
---|---|
Stage #1: 1-(benzo[d][1,3]dioxol-6-yl)ethanone With formic acid In toluene at 30 - 40℃; for 0.5h; Stage #2: With dihydrogen peroxide In toluene for 12h; Stage #3: With water at 35 - 40℃; for 4h; Concentration; Alkaline conditions; | 82.5% |
3,4-methylenedioxyphenyl formate
Sesamol
Conditions | Yield |
---|---|
With water; potassium hydroxide In methanol at 50℃; for 1h; | 82% |
With potassium hydroxide In tetrahydrofuran; methanol at 10℃; for 30h; Yield given; | |
With potassium hydroxide In methanol for 1h; Ambient temperature; Yield given; |
3,4-methylenedioxy-1-(2-tetrahydropyranyloxy)benzene
Sesamol
Conditions | Yield |
---|---|
With titanium(III) chloride In acetonitrile at 20℃; for 24h; | 81% |
Conditions | Yield |
---|---|
With ethanol; sodium hydroxide at 82 - 96℃; for 4.5h; Reflux; elimination of ethyl formate; | A 79% B n/a |
4-methoxy-3,4-(methylenedioxy)cyclohexa-2,5-dienone
A
Sesamol
Conditions | Yield |
---|---|
With lithium hexamethyldisilazane In toluene at 0℃; for 0.5h; Reflux; regioselective reaction; | A 46 mg B 72% |
Conditions | Yield |
---|---|
With copper(I) oxide; sodium methylate In methanol at 185℃; for 12h; Autoclave; | 68% |
Conditions | Yield |
---|---|
With dihydrogen peroxide; sulfuric acid In methanol for 24h; Ambient temperature; | A 67% B 8% |
Conditions | Yield |
---|---|
With dihydrogen peroxide; sulfuric acid In methanol for 24h; Ambient temperature; | A 67% B 8% |
(3,4-methylenedioxy)phenylmagnesium bromide
Sesamol
Conditions | Yield |
---|---|
With air In tetrahydrofuran at -25℃; under 12929 Torr; for 0.0566667h; Green chemistry; | 57% |
A
Sesamol
B
2-isopropyl-4,5-(methylenedioxy)phenol
Conditions | Yield |
---|---|
With potassium hydroxide In ethylene glycol Mechanism; Reflux; | A 53% B 17% |
Conditions | Yield |
---|---|
With (2’,4’,6’-triisopropyl-[1,1’-biphenyl]-2-yl)-diphenylphosphine; bis(2-phenylpyridinato)(2,2'-bipyridine)iridium(III) hexafluorophosphate; tetrabutylammomium bromide; palladium diacetate; caesium carbonate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl acetamide at 20℃; under 760.051 Torr; for 4h; Irradiation; | A 21% B 12% |
3,4-methylenedioxypropiophenone
Sesamol
Conditions | Yield |
---|---|
With formic acid; dihydrogen peroxide anschliessend Behandeln mit methanol. Kalilauge; | |
Stage #1: 3,4-methylenedioxypropiophenone With acetic anhydride; toluene-4-sulfonic acid In dichloromethane at 40℃; Stage #2: With dihydrogen peroxide In dichloromethane; water Heating / reflux; Stage #3: With hydrogenchloride In dichloromethane; water pH=1; | |
Stage #1: 3,4-methylenedioxypropiophenone In dichloromethane at 40℃; for 10h; Heating / reflux; Stage #2: With hydrogenchloride In dichloromethane; water pH=1; Heating / reflux; | |
Stage #1: 3,4-methylenedioxypropiophenone With phthalic anhydride; toluene-4-sulfonic acid In dichloromethane at 40℃; Stage #2: With dihydrogen peroxide In dichloromethane; water Heating / reflux; Stage #3: With hydrogenchloride In dichloromethane; water pH=1; | |
Stage #1: 3,4-methylenedioxypropiophenone With maleic anhydride; toluene-4-sulfonic acid In dichloromethane at 40℃; Stage #2: With dihydrogen peroxide In dichloromethane; water Heating / reflux; Stage #3: With hydrogenchloride In dichloromethane; water pH=1; |
benzo[1,3]dioxolo-5-ylamine
Sesamol
Conditions | Yield |
---|---|
Diazotization; |
Sesamol
Conditions | Yield |
---|---|
at 180℃; for 2h; Product distribution; variation of time, temperature; sesamol enhances antioxidativ action of γ-tocopherol; |
Sesamol
Conditions | Yield |
---|---|
With hydrogenchloride for 1h; Elimination; |
Sesamol
Conditions | Yield |
---|---|
With mineral acids | |
With hydrogenchloride |
Sesamol
Conditions | Yield |
---|---|
With triethylamine In various solvent(s) at 20℃; Kinetics; Further Variations:; Reagents; |
Conditions | Yield |
---|---|
With tetraethylammonium hydroxide at 0 - 20℃; for 1h; | 100% |
With sodium hydroxide In water for 1h; Heating; | 99% |
With potassium hydroxide | |
With potassium carbonate In acetone Heating; Yield given; | |
Alkaline conditions; |
Conditions | Yield |
---|---|
With potassium hydroxide In pyridine at 90℃; | 100% |
Sesamol
tert-butyldimethylsilyl chloride
(benzo[d][1,3]dioxol-5-yloxy)(tert-butyl)dimethylsilane
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; | 100% |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; | 98% |
With 1H-imidazole; dmap In N,N-dimethyl-formamide at 0 - 23℃; for 4h; Inert atmosphere; | 96% |
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 14h; silylation; | 92% |
With 1H-imidazole In dichloromethane at 20℃; for 16h; |
Conditions | Yield |
---|---|
Stage #1: Sesamol With ethylmagnesium bromide In diethyl ether at 20℃; for 0.333333h; Stage #2: 3-phenyl-propionaldehyde In dichloromethane for 20h; Heating; | 100% |
Sesamol
ethyl (E)-3-(4-methoxyphenyl)prop-2-enoate
8-(4-methoxyphenyl)-7,8-dihydro-6H-[1,3]dioxolo[4,5-g]-chromen-6-one
Conditions | Yield |
---|---|
With trifluoroacetic acid at 20℃; for 24h; | 100% |
Conditions | Yield |
---|---|
Stage #1: Sesamol With tetraethylammonium hydroxide In methanol Stage #2: dimethylsulfide In tetrahydrofuran at 20℃; for 1h; | 100% |
Conditions | Yield |
---|---|
Stage #1: Sesamol With isopropylmagnesium chloride In tetrahydrofuran at 0 - 4℃; for 2h; Industry scale; Stage #2: indole-2,3-dione In tetrahydrofuran at -5 - 3℃; Industry scale; Stage #3: With water; ammonium chloride In tetrahydrofuran at 3 - 4℃; Industry scale; | 100% |
Stage #1: Sesamol With isopropylmagnesium chloride In tetrahydrofuran at 0 - 5℃; for 2.5h; Stage #2: indole-2,3-dione In tetrahydrofuran at 0 - 20℃; for 19h; | 98% |
With potassium carbonate In tetrahydrofuran for 17h; Solvent; Inert atmosphere; | |
With triethylamine In tert-butyl methyl ether at 25℃; for 15h; Inert atmosphere; | |
In water at 20℃; |
4-(4-fluorobenzenesulfonyl)-1-prop-2-ynylpiperidine-4-carboxylic acid ethyl ester
Sesamol
C24H25NO7S
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 48h; | 100% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 0.166667h; | 100% |
Conditions | Yield |
---|---|
With potassium carbonate; bis-[(trifluoroacetoxy)iodo]benzene In acetonitrile for 0.166667h; Ambient temperature; | 99% |
Sesamol
chloromethyl methyl ether
(3,4-methylenedioxyphenoxy)methyl methyl ether
Conditions | Yield |
---|---|
With sodium hydride In N,N-dimethyl-formamide 1.) 0 deg C, 30 min, 2.) 0 deg C, 3 h; | 99% |
Stage #1: Sesamol With n-butyllithium In tetrahydrofuran at 0℃; for 0.5h; Stage #2: chloromethyl methyl ether In tetrahydrofuran at 20℃; for 24h; | 98% |
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; | 98% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 25℃; for 12h; | 99% |
With PS-BEMP; N,N-dimethyl-formamide In acetonitrile | 98% |
With PS-BEMP In N,N-dimethyl-formamide; acetonitrile at 20℃; for 3h; | 98% |
Sesamol
t-butyldimethylsiyl triflate
(benzo[d][1,3]dioxol-5-yloxy)(tert-butyl)dimethylsilane
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at -78℃; for 1h; | 99% |
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 23℃; Inert atmosphere; Schlenk technique; | 99% |
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 20h; | 95% |
With potassium carbonate at 60℃; for 3h; | |
Stage #1: Sesamol With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: benzyl bromide In N,N-dimethyl-formamide at 20℃; for 12h; |
Sesamol
(E)-3-(4-methoxyphenyl)acrylic acid
8-(4-methoxyphenyl)-7,8-dihydro-6H-[1,3]dioxolo[4,5-g]-chromen-6-one
Conditions | Yield |
---|---|
With trifluoroacetic acid In dichloromethane at 20℃; for 24h; | 99% |
With trifluoroacetic acid; palladium diacetate In dichloromethane at 20℃; for 10h; Cyclization; hydroarylation; | 96% |
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In benzene at 20℃; for 1h; | 99% |
Stage #1: Sesamol With ethylmagnesium bromide In diethyl ether at 20℃; for 0.333333h; Inert atmosphere; Stage #2: 4-methoxy-benzaldehyde In dichloromethane for 19h; Inert atmosphere; Reflux; |
Sesamol
(R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine
tert-butyl (R)-4-((R)-hydroxy(6-hydroxybenzo[d][1,3]dioxol-5-yl)methyl)-2,2-dimethyloxazolidine-3-carboxylate
Conditions | Yield |
---|---|
Stage #1: Sesamol With methylmagnesium chloride In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: (R)-3-tert-butoxycarbonyl-4-formyl-2,2-dimethyloxazolidine In dichloromethane at 0 - 20℃; for 15h; | 99% |
Conditions | Yield |
---|---|
With iron(III) chloride In dichloromethane at 20℃; for 0.333333h; Friedel Crafts alkylation; optical yield given as %de; diastereoselective reaction; | 99% |
Sesamol
(4aS,8aS)-3,4,4aα,5,6,7,8,8aβ-octahydro-5,5,8aβ-trimethyl-1-methylidene-2(1H)-naphthalenone
(12bS)-9,10-methylenedioxy-4,4,12b-trimethyl-2,3,4,4a,5,6,12,12b-octahydro-1Hbenzo[a]xanthene
Conditions | Yield |
---|---|
With Amberlyst A-15 ion exchange resin In benzene for 1.83333h; Friedel Crafts alkylation; Inert atmosphere; Reflux; Molecular sieve; | 99% |
Conditions | Yield |
---|---|
With C36H45F12N7S2 In toluene at 20℃; for 12h; Friedel Crafts reaction; optical yield given as %ee; enantioselective reaction; | 99% |
With C36H45F12N7S2 In toluene at 20℃; for 12h; Friedel Crafts reaction; optical yield given as %ee; stereoselective reaction; | 99% |
Conditions | Yield |
---|---|
With C36H45F12N7S2 In toluene at 20℃; for 12h; Friedel Crafts reaction; optical yield given as %ee; enantioselective reaction; | 99% |
With C36H45F12N7S2 In toluene at 0℃; for 12h; Friedel Crafts reaction; optical yield given as %ee; stereoselective reaction; | 91% |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; | 99% |
Sesamol
1-benzyloxyallene
Conditions | Yield |
---|---|
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; N,N’-(1S,2S)-cyclohexane-1,2-diylbis[2-(diphenylphosphino)-1-naphthamide]; triethylamine In 1,4-dioxane at 15℃; for 12h; Schlenk technique; Molecular sieve; enantioselective reaction; | 99% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In nitromethane at 80℃; for 3h; | 99% |
With 3-(1,1-dioxido-4-(3-(3-(3-sulfopropyl)-1H-imidazol-3-ium-1-yl)propyl)thiomorpholino-4-ium)propane-1-sulfonate trifluoromethanesulfonate In acetic acid butyl ester at 80℃; for 2h; | 99% |
Sesamol
ethyl (1-benzyl-2-oxo-2,3-dihydro-1H-indol-3-ylidene)cyanoacetate
Conditions | Yield |
---|---|
With C29H28F6N4OS at 25℃; Molecular sieve; enantioselective reaction; | 99% |
Conditions | Yield |
---|---|
With C29H28F6N4OS at 25℃; Molecular sieve; enantioselective reaction; | 99% |
Conditions | Yield |
---|---|
With C29H28F6N4OS at 25℃; Molecular sieve; enantioselective reaction; | 99% |
Conditions | Yield |
---|---|
With C29H28F6N4OS at 25℃; Molecular sieve; enantioselective reaction; | 99% |
Conditions | Yield |
---|---|
With C29H28F6N4OS at 25℃; Molecular sieve; enantioselective reaction; | 99% |
Conditions | Yield |
---|---|
With C29H28F6N4OS at 25℃; Molecular sieve; enantioselective reaction; | 99% |
Reported in EPA TSCA Inventory.
1. Introduction of Sesamol
Sesamol is a natural organic compound which is a component of sesame oil. It has been found to be an antioxidant that may prevent the spoilage of oils, and may protect the body from damage from free radicals. The IUPAC Name of it is 1,3-benzodioxol-5-ol.
2. Properties of Sesamol
Melting Point: 62-65 °C(lit.)
Boiling point: 274 °C at 760 mmHg
Storage Temperature: -20°C
Flash Point: 119.5 °C
Density: 1.394 g/cm3
Water Solubility: slightly soluble
Index of Refraction: 1.609
Molar Refractivity: 34.29 cm3
Molar Volume: 99 cm3
Surface Tension: 61.7 dyne/cm
Enthalpy of Vaporization: 53.3 kJ/mol
Vapour Pressure: 0.00331 mmHg at 25°C
XLogP3-AA: 1.2
H-Bond Donor: 1
H-Bond Acceptor: 3
3. Structure Descriptors of Sesamol
Canonical SMILES: C1OC2=C(O1)C=C(C=C2)O
InChI: InChI=1S/C7H6O3/c8-5-1-2-6-7(3-5)10-4-9-6/h1-3,8H,4H2
InChIKey: LUSZGTFNYDARNI-UHFFFAOYSA-N
4. Toxicity of Sesamol
1. | orl-mus TDLo:1092 g/kg/2Y-C:CAR | JJCREP Japanese Journal of Cancer Research (Gann). 83 (1992),1279. | ||
2. | orl-mus LD:1612 g/kg/96W-C:CAR | JJCREP Japanese Journal of Cancer Research (Gann). 81 (1990),207. |
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