methyl (3,4,5-trimethoxyphenyl) ketone
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
Conditions | Yield |
---|---|
With lithium thioethoxide In N,N-dimethyl-formamide at 70℃; for 0.25h; Inert atmosphere; Microwave irradiation; regioselective reaction; | 95% |
With magnesium iodide for 0.5h; neat (no solvent); | 90% |
With zirconium(IV) chloride; methoxybenzene In dichloromethane at 40℃; for 48h; Sealed tube; | 63% |
methyl 4-O-tert-butyldimethylsilyl-3,5-dimethoxybenzoate
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride | 92% |
1-(4-Hydroxy-3,5-dimethoxyphenyl)ethanol
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
Conditions | Yield |
---|---|
With copper diacetate; ethylene glycol at 50℃; for 8h; Green chemistry; chemoselective reaction; | 91% |
4-ethylsyringol
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
Conditions | Yield |
---|---|
With copper diacetate; ethylene glycol at 90℃; for 12h; Green chemistry; chemoselective reaction; | 84% |
C11H16O4
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
Conditions | Yield |
---|---|
With copper diacetate; ethylene glycol at 50℃; for 8h; Green chemistry; chemoselective reaction; | 83% |
1-(4-Hydroxy-3,5-dimethoxyphenyl)ethanol
A
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
B
2,6-dimethoxy-p-quinone
Conditions | Yield |
---|---|
With oxygen; (pyridine)cobalt In methanol under 2585.7 Torr; for 24h; Ambient temperature; Title compound not separated from byproducts; | A 4 % Spectr. B 82% |
With oxygen; (pyridine)cobalt In methanol under 2585.7 Torr; for 24h; Ambient temperature; | A 4 % Spectr. B 82% |
acetic acid 2,6-dimethoxy-phenyl ester
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
Conditions | Yield |
---|---|
With bismuth(lll) trifluoromethanesulfonate In toluene for 1h; Fries rearrangement; Heating; | 80% |
With aluminum (III) chloride In nitrobenzene at 0℃; Solvent; Reagent/catalyst; | 80% |
With aluminium trichloride; nitrobenzene at 2 - 3℃; dann bei Zimmertemperatur; | |
With aluminium trichloride; nitrobenzene | |
With aluminium trichloride In nitrobenzene |
3,3'-dimethoxy-4-carboxymethoxyacetophenone
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
Conditions | Yield |
---|---|
Stage #1: 3,3'-dimethoxy-4-carboxymethoxyacetophenone With triethylamine In N,N-dimethyl-formamide; toluene for 3h; Curtius rearrangement; Heating; Stage #2: With potassium hydroxide; glycerol In ethanol; N,N-dimethyl-formamide; toluene for 2h; Heating; Further stages.; | 70% |
1-(4-hydroxy-3-iodo-5-methoxy-phenyl)ethan-1-one
sodium methylate
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
Conditions | Yield |
---|---|
With methanol; copper at 140℃; |
1-(4-hydroxy-3,5-dimethoxyphenyl)ethanone benzyl ether
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
Conditions | Yield |
---|---|
With hydrogen bromide; acetic acid bei gewoehnlicher Temperatur; |
1,3-dimethoxy-2-hydroxy-benzene
acetic acid
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
Conditions | Yield |
---|---|
With boron trifluoride |
pyrrolidine
1-(4-acetoxy-3,5-dimethoxy-phenyl)-ethanone
A
N-(acetyl)pyrrolidine
B
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
Conditions | Yield |
---|---|
for 0.05h; Ambient temperature; |
1,3-dimethoxy-2-hydroxy-benzene
acetyl chloride
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
Conditions | Yield |
---|---|
(i), (ii) AlCl3, PhNO2; Multistep reaction; |
4-amino-butyric acid 2-(4-hydroxy-3,5-dimethoxy-phenyl)-2-oxo-ethyl ester
A
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
B
3',5'-dimethoxy-4'-hydroxy-(2-hydroxy)acetophenone
C
4-amino-n-butyric acid
Conditions | Yield |
---|---|
With water Hydrolysis; reduction; UV-irradiation; |
A
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
B
(E)-sinapinaldehyde
C
1-(3,5-dimethoxy-4-hydroxyphenyl)propan-2-one
Conditions | Yield |
---|---|
With air Oxidation; Formation of xenobiotics; Further byproducts given; |
1-(3,5-dimethoxyphenyl)ethan-1-one
A
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
B
2ʹ-hydroxy-3ʹ,5ʹ-dimethoxyacetophenone
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid; 3-chloro-benzenecarboperoxoic acid In acetonitrile at 80℃; for 2h; | A 3 % Chromat. B 11 % Chromat. |
A
L-glutamic acid
B
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
C
3',5'-dimethoxy-4'-hydroxy-(2-hydroxy)acetophenone
Conditions | Yield |
---|---|
With water Hydrolysis; reduction; UV-irradiation; |
2-bromo-1-(4-hydroxy-3,5-dimethoxyphenyl)ethanone
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: DBU / dioxane / 12 h / 0 - 20 °C 2: TFA / 4 h / 0 °C 3: H2O / UV-irradiation View Scheme | |
Multi-step reaction with 3 steps 1: 67 percent / DBU / benzene / 12 h / 20 °C 2: 98 percent / TFA / 4 h / 0 °C 3: H2O / UV-irradiation View Scheme |
4-tert-butoxycarbonylamino-butyric acid 2-(4-hydroxy-3,5-dimethoxy-phenyl)-2-oxo-ethyl ester
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: TFA / 4 h / 0 °C 2: H2O / UV-irradiation View Scheme |
γ-O-(3,5-dimethoxy-4-hydroxyphenacyl) t-butyl N-t-boc L-glutamate
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 98 percent / TFA / 4 h / 0 °C 2: H2O / UV-irradiation View Scheme |
1-(3-methoxy-4-hydroxyphenyl)ethanone
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aqueous KI; NaHCO3; iodine 2: copper; methanol / 140 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: pyridine; benzene / anschliessendes Erwaermen auf 60grad 2: AlCl3; nitrobenzene View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: NaOH-solution 2: benzene; phosphorus pentachloride / 0 °C 3: alcohol; diethyl ether 4: ammonium chloride; diluted ammonia 5: water / 175 - 180 °C 6: hydrogen bromide; glacial acetic acid / bei gewoehnlicher Temperatur View Scheme |
methyl 4-benzyloxy-3,5-dimethoxybenzoate
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: NaOH-solution / durch Verseifung 2: benzene; phosphorus pentachloride / 0 °C 3: alcohol; diethyl ether 4: ammonium chloride; diluted ammonia 5: water / 175 - 180 °C 6: hydrogen bromide; glacial acetic acid / bei gewoehnlicher Temperatur View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: methanolic KOH-solution 2: NaOH-solution / durch Verseifung 3: benzene; phosphorus pentachloride / 0 °C 4: alcohol; diethyl ether 5: ammonium chloride; diluted ammonia 6: water / 175 - 180 °C 7: hydrogen bromide; glacial acetic acid / bei gewoehnlicher Temperatur View Scheme |
ethyl 3-(4-benzyloxy-3,5-dimethoxyphenyl)-3-oxopropionate
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: water / 175 - 180 °C 2: hydrogen bromide; glacial acetic acid / bei gewoehnlicher Temperatur View Scheme |
4-benzyloxy-3,5-dimethoxybenzoic acid chloride
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: alcohol; diethyl ether 2: ammonium chloride; diluted ammonia 3: water / 175 - 180 °C 4: hydrogen bromide; glacial acetic acid / bei gewoehnlicher Temperatur View Scheme |
2-(4-benzyloxy-3,5-dimethoxy-benzoyl)-3-oxo-butyric acid ethyl ester
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: ammonium chloride; diluted ammonia 2: water / 175 - 180 °C 3: hydrogen bromide; glacial acetic acid / bei gewoehnlicher Temperatur View Scheme |
4-(benzyloxy)-3,5-dimethoxybenzoic acid
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: benzene; phosphorus pentachloride / 0 °C 2: alcohol; diethyl ether 3: ammonium chloride; diluted ammonia 4: water / 175 - 180 °C 5: hydrogen bromide; glacial acetic acid / bei gewoehnlicher Temperatur View Scheme |
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
acetyl chloride
1-(4-acetoxy-3,5-dimethoxy-phenyl)-ethanone
Conditions | Yield |
---|---|
With potassium carbonate; triethylamine In dichloromethane | 99% |
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
3,5-bis(trifluoromethyl)benzyl bromide
Conditions | Yield |
---|---|
With sodium hydroxide In water; acetonitrile for 5h; Heating; | 95% |
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
Conditions | Yield |
---|---|
With hydroxylamine hydrochloride; sodium acetate In methanol; water at 60℃; | 93% |
With hydroxylamine hydrochloride; sodium acetate In water at 80℃; for 2h; | 47% |
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
ethyl bromoacetate
ethyl (4-acetyl-2,6-dimethoxyphenoxy)acetate
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide for 18h; | 90% |
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2-(tert-butyldimethylsilyloxy)ethanol
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0 - 20℃; Mitsunobu reaction; | 87% |
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
Conditions | Yield |
---|---|
With iodine; Selectfluor In methanol at 22℃; for 24h; | 81% |
9-methyl-9H-carbazole-3-carbaldehyde
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
Conditions | Yield |
---|---|
With piperidine In ethanol for 3h; Claisen-Schmidt Condensation; Reflux; | 79% |
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
ethylene glycol
2,6-dimethoxy-4-(2-methyl-[1,3]dioxolan-2-yl)-phenol
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid; orthoformic acid triethyl ester | 75% |
Conditions | Yield |
---|---|
With bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane | 69% |
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
2-bromo-1-(4-hydroxy-3,5-dimethoxyphenyl)ethanone
Conditions | Yield |
---|---|
With copper(ll) bromide In chloroform; ethyl acetate at 20℃; for 21h; Bromination; | 68% |
With bromine In chloroform | |
With bromine In 1,4-dioxane; diethyl ether at 0℃; for 1h; |
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
isopropyl bromide
3',5'-dimethoxy-4'-isopropoxyacetophenone
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide for 4.5h; Heating; | 65.9% |
Conditions | Yield |
---|---|
Stage #1: 1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone With selenium(IV) oxide; ytterbium(III) chloride In water; dimethyl sulfoxide at 110℃; for 15h; Green chemistry; Stage #2: 1,2,3-trimethoxybenzene In water; dimethyl sulfoxide at 70℃; for 0.166667h; Green chemistry; | 65% |
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
DL-tryptophan methyl ester
C22H18N2O6
Conditions | Yield |
---|---|
Stage #1: 1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone With iodine; dimethyl sulfoxide at 90℃; Stage #2: DL-tryptophan methyl ester | 64% |
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
A
1-(3,4-dihydroxy-5-methoxyphenyl)-ethan-1-one
B
1-(3,4,5-trihydroxyphenyl)-ethan-1-one
Conditions | Yield |
---|---|
With methylimidazolium bromide at 110℃; Irradiation; | A 63% B 26% |
Methyl 4-bromobutyrate
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
4-(4-Acetyl-2,6-dimethoxy-phenoxy)-butyric acid methyl ester
Conditions | Yield |
---|---|
60% | |
With 18-crown-6 ether; potassium carbonate In butanone 1.) reflux, 48 h, 2.) reflux, 1 h; | 60% |
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
4-hydroxy-benzaldehyde
1-(4-hydroxy-3,5-dimethoxyphenyl)-3-(4-hydroxyphenyl)-prop-2-enone
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 24h; | 60% |
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; copper(l) iodide; hydroquinone In water; dimethyl sulfoxide at 30℃; for 24h; pH=5.5; Catalytic behavior; Reagent/catalyst; Solvent; Sealed tube; | 58% |
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
(E)-2-allyl-6-iodohepta-2,6-dienoic acid
C20H23IO6
Conditions | Yield |
---|---|
Stage #1: (E)-2-allyl-6-iodohepta-2,6-dienoic acid With diphenic acid; lead(IV) tetraacetate In dichloromethane at 0 - 20℃; Inert atmosphere; Stage #2: 1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone In dichloromethane at 0 - 20℃; for 2.25h; | 54% |
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
C20H23BrO6
Conditions | Yield |
---|---|
Stage #1: (E)-2-allyl-6-bromohepta-2,6-dienoic acid With diphenic acid; lead(IV) tetraacetate In dichloromethane for 0.333333h; Inert atmosphere; Stage #2: 1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone In dichloromethane at 0 - 20℃; for 1.41667h; | 48% |
isovanillin
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
(E)-1-(4-hydroxy-3,5-dimethoxyphenyl)-3-(3-hydroxy-4-methoxyphenyl)prop-2-en-1-one
Conditions | Yield |
---|---|
Stage #1: isovanillin; 1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone In ethanol at 20℃; for 0.0833333h; Stage #2: With sodium hydroxide In ethanol at 20℃; | 48% |
1-(4-hydroxy-3,5-dimethoxy-phenyl)-ethanone
phenyl 2,3,4,6-tetra-O-benzyl-1-sulfinyl-α/β-D-glucopyranoside
Conditions | Yield |
---|---|
With 2,6-di-tert-butyl-4-methylpyridine In dichloromethane at 20℃; | 46% |
Conditions | Yield |
---|---|
With 1,1,1,3',3',3'-hexafluoro-propanol; bis-[(trifluoroacetoxy)iodo]benzene In dichloromethane at 20℃; for 2.5h; Inert atmosphere; | 34% |
The Acetosyringone, with CAS registry number 2478-38-8, belongs to the following product category: Aromatic Acetophenones & Derivatives (substituted). Its systematic name and its IUPAC name are the same, which is 1-(4-hydroxy-3,5-dimethoxyphenyl)ethanone. And this chemical is a kind of beige to light brown crystalline powder.
Physical properties of Acetosyringone are: (1)ACD/LogP: 1.699; (2)ACD/LogD (pH 5.5): 1.70; (3)ACD/LogD (pH 7.4): 1.63; (4)ACD/BCF (pH 5.5): 11.49; (5)ACD/BCF (pH 7.4): 9.92; (6)ACD/KOC (pH 5.5): 199.64; (7)ACD/KOC (pH 7.4): 172.35; (8)#H bond acceptors: 4; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 4; (11)Index of Refraction:1.528; (12)Molar Refractivity: 51.519 cm3; (13)Molar Volume: 167.398 cm3; (14)Polarizability: 20.424 10-24cm3; (15)Surface Tension: 39.9329986572266 dyne/cm; (16)Density: 1.172 g/cm3; (17)Flash Point: 131.705 °C; (18)Enthalpy of Vaporization: 60.054 kJ/mol; (19)Boiling Point: 334.653 °C at 760 mmHg
Preparation of Acetosyringone: This chemical can be prepared by 1-(3,4,5-trimethoxy-phenyl)-ethanone. This reaction will need reagent AlCl3. The yield is about 60%.
Uses of Acetosyringone: It can be used to produce 3',5'-dimethoxy-4'-isopropoxyacetophenone. This reaction will need reagent K2CO3 and solvent dimethylformamide. The reaction time is 4.5 hour(s). The yield is about 65.9%.
When you are using this chemical, please be cautious about it as the following:
The Acetosyringone irritates to eyes, respiratory system and skin. When use it, wear suitable protective clothing, gloves and eye/face protection. If contact with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1)InChI=1S/C10H12O4/c1-6(11)7-4-8(13-2)10(12)9(5-7)14-3/h4-5,12H,1-3H3;
(2)InChIKey=OJOBTAOGJIWAGB-UHFFFAOYSA-N;
(3)Smilesc1(c(c(cc(c1)C(C)=O)OC)O)OC;
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intraperitoneal | 650mg/kg (650mg/kg) | BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) | Journal of Medicinal Chemistry. Vol. 7, Pg. 178, 1964. |
mouse | LD50 | oral | > 10gm/kg (10000mg/kg) | Bromatologia i Chemia Toksykologiczna. Vol. 14, Pg. 301, 1981. |
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