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CAS No. : | 22139-77-1 | MDL No. : | MFCD00210544 |
Formula : | C14H12O2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YCVPRTHEGLPYPB-VOTSOKGWSA-N |
M.W : | 212.24 | Pubchem ID : | 5280457 |
Synonyms : |
trans-3,5-Dihydroxystilbene
|
Num. heavy atoms : | 16 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 65.86 |
TPSA : | 40.46 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.12 cm/s |
Log Po/w (iLOGP) : | 2.05 |
Log Po/w (XLOGP3) : | 3.48 |
Log Po/w (WLOGP) : | 3.05 |
Log Po/w (MLOGP) : | 2.87 |
Log Po/w (SILICOS-IT) : | 3.07 |
Consensus Log Po/w : | 2.9 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -3.77 |
Solubility : | 0.0359 mg/ml ; 0.000169 mol/l |
Class : | Soluble |
Log S (Ali) : | -4.01 |
Solubility : | 0.0206 mg/ml ; 0.0000973 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -3.86 |
Solubility : | 0.0292 mg/ml ; 0.000138 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.98 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine hydrochloride at 180℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydroxide; ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
35% | With potassium carbonate In acetone Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | With potassium carbonate In acetone for 24h; Reflux; Inert atmosphere; | |
20% | With potassium carbonate In acetone Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
41% | With potassium carbonate In acetone Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With boron trifluoride diethyl etherate at 25℃; for 40h; Yield given. Yields of byproduct given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
26% | With potassium carbonate In acetone Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | With potassium carbonate In acetone Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With potassium carbonate In acetone Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | With potassium carbonate In acetone Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With hydrogen In ethanol for 1h; | |
With hydrogen Yield given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | With pyridine hydrochloride at 190℃; for 4h; | |
83% | With boron tribromide In dichloromethane at -20 - 20℃; Inert atmosphere; | |
83% | With boron tribromide In dichloromethane at -20 - 20℃; Inert atmosphere; | 1 E-1-(2-(3,5-dimethoxyphenyl)vinyl)benzene, 0.2 mmol,48mg, dissolved in 6mL anhydrous dichloromethane under nitrogen protection,Stir at -20 ° C and slowly add 0.34 g, 1.34 mmol of boron tribromide.30% was dissolved in anhydrous dichloromethane. The mixture is stirred under nitrogen,And slowly rise to room temperature, the reaction is 4 ~ 5h, after the reaction is completed, add 10ml of water,The mixture was extracted three times with dichloromethane, washed with brine and dried over anhydrous sodium sulfate.The crude product was concentrated under reduced pressure and purified by column chromatography (hexane/hexane = 6/4).Get silver pine,White solid 35 mg, yield 83%. |
83% | With boron tribromide In dichloromethane at -20 - 20℃; Inert atmosphere; | 2 (2) Add 0.2mmol of (E-1,2-bis(4-methoxyphenyl)vinyl)benzene to 6mL of anhydrous dichloromethane under the protection of nitrogen to dissolve, stir and slowly add dropwise at -20 1.34mmol of boron tribromide (0.34 g, 30% dissolved in anhydrous dichloromethane), the mixture is stirred under nitrogen protection, and slowly rises to room temperature to react for 4~5h. After the reaction is completed, add 10ml of water and dichloromethane Extracted 3 times, washed with brine, and dried over anhydrous sodium sulfate; concentrated under reduced pressure and purified by column chromatography (n-hexane/acetone=6/4) to obtain silver pintin, white solid 35mg, reaction yield 83%. |
80% | With boron tribromide-dimethyl sulfide complex In 1,2-dichloro-ethane | |
32% | With boron tribromide In dichloromethane at 5℃; Reflux; | |
29% | With boron tribromide In dichloromethane at -10 - 20℃; for 24h; Inert atmosphere; | 2. General procedure for demethylation of stilbene 4 General procedure: In 6 mL of anhydrous methylene chloride, 200 mg of methoxy-stilbene 4 (0.74 mmol) was dissolved and cooled to -10 °C under argon. BBr3 (0.6 mL, 6.3 mmol, 17% in dichloromethane) in anhydrous methylene chloride (5 mL) was added slowly, and the mixture was allowed to reach to room temperature for 3-24 h. Water was added to destroy the excess BBr3, and the mixture was extracted twice with ethyl acetate. The organic extracts were washed with water and brine and dried, and the solvent evaporated. The crude product was purified by column chromatography on silica gel (20% EtOAc in hexane) yielding resveratrol and derivatives 1. |
13 mg | With pyridine hydrochloride at 190℃; for 3h; | |
With pyridine hydrochloride at 190℃; for 4h; | ||
With pyridine hydrochloride at 190℃; for 4h; | ||
With pyridine hydrochloride at 190℃; | ||
With hydrogenchloride; pyridine hydrochloride | 1.e 3rd Step 3rd Step For demethylation, a homogeneous mixture of 54.0 g (0.22 mol) of 3,5-dimethoxystilbene and 40.0 g (0.35 mol) of pyridine hydrochloride is heated at about 165° C. for 3 hours. The cooled, oily reaction mass is then introduced into 1.2 liters of 2N hydrochloric acid and the crude product is isolated by extraction with diethyl ether. Recrystallisation from toluene yields 3,5-dlihydroxystilbene in the form of a pale-yellow powder. Yield: 26.0 g (0.12 mol; 41.0% of theory) | |
With pyridine hydrochloride at 180 - 200℃; Inert atmosphere; | ||
69 mg | With boron tribromide In dichloromethane at 0 - 20℃; Schlenk technique; Inert atmosphere; | |
62 mg | With boron tribromide In dichloromethane at -20℃; Inert atmosphere; diastereoselective reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 43% 2: 51% | With boron tribromide In dichloromethane at 0 - 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With hydrogen In dichloromethane at 20℃; for 5h; | 11 A solution of 21.1 g of 3,5_-dibenzyloxystilb was dissolved in 120 mL of CH2C12, and then 10.38 g of a catalyst having a loading of 5% Pd was charged at a pressure of 5 to 5 MPa, and the reaction was carried out at room temperature for 5 hours. After the completion of the reaction, The filtrate was recovered by filtration to recover the reaction solvent to obtain the crude product. The crude product was recrystallized from ethanol to give 9.5 g of pinosylvin in a yield of 90%. |
70% | With palladium 10% on activated carbon; ammonium formate In methanol; 1,2-dichloro-ethane at 40℃; for 0.75h; | 7 Embodiment 7 Weighing 0 . 20 g of formula II - 6 shown (E)-1-phenyl-2-(3,5-dibenzyloxyphenyl)ethylene and 0 . 18 g ammonium formate in 6 ml mixed solvent (1, 2 - dichloroethane/methanol=1/1) by heating to 40 °C, stirring 15 minutes, the raw material is dissolved. The insulation by adding 0 . 026 g 10% palladium-carbon catalyst, thermal insulation stirring TLC monitoring until the reaction is complete, about 30 minutes. Filtering to remove the palladium-carbon, reducing pressure of the mother liquor solvent, residue by column chromatography separation to obtain the target product I - 6 indicated by the 5-[(1E)-2-phenylvinyl]-1,3-benzenediol 0.076g, yield 70%. |
58% | With aluminium trichloride; <i>N</i>,<i>N</i>-dimethyl-aniline In dichloromethane at 0℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
34% | With potassium carbonate In acetone Heating; | |
12% | With potassium carbonate In acetone for 24h; Reflux; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
99% | With diphenyldisulfane In tetrahydrofuran for 0.5h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 64% 2: 13% | With iodine In benzene for 5h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen fluoride In acetonitrile for 4h; Ambient temperature; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | With potassium carbonate In acetone Heating; | |
28% | With potassium carbonate In acetone for 24h; Reflux; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With boron trifluoride diethyl etherate In 1,4-dioxane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With boron trifluoride diethyl etherate In 1,4-dioxane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With boron trifluoride diethyl etherate In 1,4-dioxane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With boron trifluoride diethyl etherate In 1,4-dioxane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(i) KOH, MeOH, (ii) aq. NaOH; Multistep reaction; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogen bromide In acetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With quinoline; copper at 240 - 260℃; Kochen des Reaktionsprodukts mit wss. NaOH; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | In toluene; butan-1-ol for 4h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With potassium carbonate In acetone | |
18% | With potassium carbonate In acetone for 24h; Reflux; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
11% | With phosphate buffer; Streptococcus mutans at 37℃; for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With pyridine In dichloromethane at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
44% | With pyridine In dichloromethane at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28% | With pyridine In dichloromethane at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 50 percent / K2CO3 / acetone 2: 98 percent / K2CO3 / acetone |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: NaOMe / dimethylformamide / 0 °C 1.2: dimethylformamide / 20 °C 2.1: pyridine hydrochloride / 190 °C | ||
Multi-step reaction with 2 steps 1: 35.1 g 2: 13 mg / pyridine hydrochloride / 3 h / 190 °C | ||
Multi-step reaction with 2 steps 1: 1.) potassium tert-butoxide, 2.) diphenyl disulfide / 1.) THF, 30 min, 2.) THF, reflux, 4 h 2: 51 percent / BBr3 / CH2Cl2 / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: NaOMe / dimethylformamide / 0 °C 1.2: dimethylformamide / 20 °C 2.1: pyridine hydrochloride / 190 °C | ||
Multi-step reaction with 2 steps 1: 35.1 g 2: 13 mg / pyridine hydrochloride / 3 h / 190 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: 130 °C 2.1: NaOMe / dimethylformamide / 0 °C 2.2: dimethylformamide / 20 °C 3.1: pyridine hydrochloride / 190 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: triethyl phosphate / 130 °C 1.2: NaOMe / dimethylformamide / 20 - 100 °C 2.1: pyridine hydrochloride / 4 h / 190 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: gaseous HBr / benzene / 1 h / 78 °C 2.1: triethyl phosphate / 130 °C 2.2: NaOMe / dimethylformamide / 20 - 100 °C 3.1: pyridine hydrochloride / 4 h / 190 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: Et3N / tetrahydrofuran / 1 h / 0 - 20 °C 2: 37 percent / Li, naphthalene / tetrahydrofuran / 2 h / -30 - 0 °C 3: 75 percent / phosphoric acid / toluene / 2 h / Heating 4: 80 percent / BBr3*Me2S / 1,2-dichloro-ethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 37 percent / Li, naphthalene / tetrahydrofuran / 2 h / -30 - 0 °C 2: 75 percent / phosphoric acid / toluene / 2 h / Heating 3: 80 percent / BBr3*Me2S / 1,2-dichloro-ethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 75 percent / phosphoric acid / toluene / 2 h / Heating 2: 80 percent / BBr3*Me2S / 1,2-dichloro-ethane |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1.) potassium tert-butoxide, 2.) diphenyl disulfide / 1.) THF, 30 min, 2.) THF, reflux, 4 h 2: 51 percent / BBr3 / CH2Cl2 / 0 - 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: 94 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 2: 95 percent / lithium aluminium hydride / diethyl ether / 1.) 30 min 2.) reflux, 1 h 3: 86 percent / Ph3P / CCl4 / 2 h / 75 - 80 °C 4: 83 percent / xylene / 10 h / Heating 5: 1.) n-BuLi / 1.) benzene, 30 min 2.) benzene, 4 h 6: 40percent aq. HF / acetonitrile / 4 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1.) n-BuLi / 1.) benzene, 30 min 2.) benzene, 4 h 2: 40percent aq. HF / acetonitrile / 4 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 95 percent / lithium aluminium hydride / diethyl ether / 1.) 30 min 2.) reflux, 1 h 2: 86 percent / Ph3P / CCl4 / 2 h / 75 - 80 °C 3: 83 percent / xylene / 10 h / Heating 4: 1.) n-BuLi / 1.) benzene, 30 min 2.) benzene, 4 h 5: 40percent aq. HF / acetonitrile / 4 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 86 percent / Ph3P / CCl4 / 2 h / 75 - 80 °C 2: 83 percent / xylene / 10 h / Heating 3: 1.) n-BuLi / 1.) benzene, 30 min 2.) benzene, 4 h 4: 40percent aq. HF / acetonitrile / 4 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 83 percent / xylene / 10 h / Heating 2: 1.) n-BuLi / 1.) benzene, 30 min 2.) benzene, 4 h 3: 40percent aq. HF / acetonitrile / 4 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 1.) n-BuLi / 1.) benzene, 30 min 2.) benzene, 4 h 2: 40percent aq. HF / acetonitrile / 4 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: H2 / 10percent Pd-C 2: 1) NaOMe / 1) methanol, room temp., 30 min, 2) benzene, 50-55 deg C, 30 min |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: H2 / 10percent Pd-C 2: 1) NaOMe / 1) methanol, room temp., 30 min, 2) benzene, 50-55 deg C, 30 min 3: 5 mg / m-CPBA / CHCl3 / 2 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: H2 / 10percent Pd-C 2: 1) NaOMe / 1) methanol, room temp., 30 min, 2) benzene, 50-55 deg C, 30 min |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: H2 / 10percent Pd-C 2: 1) NaOMe / 1) methanol, room temp., 30 min, 2) benzene, 50-55 deg C, 30 min |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: BF3*Et2O / 40 h / 25 °C 2: 100 percent / K2CO3 / dimethylformamide / 20 h / 85 °C 3: 96 percent / NaIO4, OsO4 / dioxane; H2O / 15 h / 25 °C 4: 96 percent / potassium tri-sec-butylborohydride / tetrahydrofuran / 0.5 h / -78 °C 5: NaH / diethyl ether / 1 h / 15 °C 6: 1) Et3N, 2) 2 N KOH / 1) MeOH, ether, 18 h, 25 deg C, 2) 0 deg C, 15 min, MeOH |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: BF3*Et2O / 40 h / 25 °C 2: 100 percent / K2CO3 / dimethylformamide / 20 h / 85 °C 3: 96 percent / NaIO4, OsO4 / dioxane; H2O / 15 h / 25 °C 4: 96 percent / potassium tri-sec-butylborohydride / tetrahydrofuran / 0.5 h / -78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: BF3*Et2O / 40 h / 25 °C 2: 100 percent / K2CO3 / dimethylformamide / 20 h / 85 °C 3: 96 percent / NaIO4, OsO4 / dioxane; H2O / 15 h / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: BF3*Et2O / 40 h / 25 °C 2: 100 percent / K2CO3 / dimethylformamide / 20 h / 85 °C 3: 96 percent / NaIO4, OsO4 / dioxane; H2O / 15 h / 25 °C 4: 96 percent / potassium tri-sec-butylborohydride / tetrahydrofuran / 0.5 h / -78 °C 5: NaH / diethyl ether / 1 h / 15 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: BF3*Et2O / 40 h / 25 °C 2: 100 percent / K2CO3 / dimethylformamide / 20 h / 85 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: ethanol; aqueous NaOH 2: diethyl ether; platinum / Hydrogenation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: ethanol; aqueous NaOH 2: diethyl ether; platinum / Hydrogenation 3: bromine |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 160 - 170 °C 2: H2 / Pd-C / ethanol 3: (i) KOtBu, DMF, (ii) /BRN= 471223/, toluene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: H2 / Pd-C / ethanol 2: (i) KOtBu, DMF, (ii) /BRN= 471223/, toluene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With ethylenediamine diacetic acid; triethylamine In 5,5-dimethyl-1,3-cyclohexadiene for 24h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With ethylenediamine diacetic acid; triethylamine In 5,5-dimethyl-1,3-cyclohexadiene for 24h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 23% 2: 40% | With ethylenediamine diacetic acid In para-xylene for 10h; Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With ethylenediamine diacetic acid In benzene for 12h; Reflux; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With ethylenediamine diacetic acid In benzene for 12h; Reflux; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With ethylenediamine diacetic acid In para-xylene for 8h; Reflux; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | With ethylenediamine diacetic acid In para-xylene for 12h; Reflux; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With ethylenediamine diacetic acid In para-xylene for 8h; Reflux; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | With ethylenediamine diacetic acid In benzene for 12h; Reflux; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With ethylenediamine diacetic acid In benzene for 10h; Reflux; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 40% 2: 23% | With ethylenediamine diacetic acid In para-xylene at 138℃; for 10h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 9 mg 2: 15 mg | With tetrabutyl ammonium fluoride In tetrahydrofuran for 0.333333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / 0 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere 3.1: pyridine; trichlorophosphate / 0 - 100 °C / Inert atmosphere 4.1: hydrogenchloride; water / methanol / 10 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / 0 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / 0 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / 0 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere 3.1: pyridine; trichlorophosphate / 0 - 100 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / 0 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere 3.1: hydrogenchloride; water / methanol / 10 h / 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | With ethylenediamine diacetic acid In benzene for 10h; Inert atmosphere; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
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With hydrogenchloride; potassium hydroxide In methanol; hexane; water; ethyl acetate | 12 Example 12 Example 12 (E)-3,5-Dihydroxystilbene, [(E)-5-styrylbenzene-1,3-diol] (12). A solution of potassium hydroxide in methanol was added to (E)-5-styryl-1,3-phenylene diacetate suspended in methanol. The solution was heated under a nitrogen atmosphere to 70° C. for 100 minutes. Upon cooling to room temperature, the solution was acidified to pH 3 by addition of 1 M HCl. Water was added, and the volume reduced by rotary evaporation and stopped at the first appearance of a precipitate. Ethyl acetate was added and the organic layer was separated and washed four times with water until the aqueous washings were neutral. The organic material was then dried, filtered and rotary evaporated to give an orange oil. Purification by gradient elution column chromatography (2:1 hexane/EtOAc to 1:1 hexane/EtOAc) gave (E)-5-styrylbenzene-1,3-diol as a white solid. Rf 0.17 (hexane/EtOAc 4:1), 0.62 (hexane/EtOAc 1:1); mp 157.0-157.5° C., 1H NMR (CD3OD): δ 6.18 (pseudo t, 1H, J=2.2 Hz, H-4), 6.46 (d, 2H, J=2.2 Hz, H-2, H-6), 6.95 (d, 1H, J=16.3 Hz, Htrans) 7.01 (d, 1H, J=16.3 Hz, Htrans), 7.15-7.21 (m, 1H, H-4'), 7.26-7.32 (m, 2H, H-3', H-5'), 7.44-7.48 (m, 2H, 2', 6'); 13C JMOD NMR (CD3OD): δ 100.91 (4), 103.92 (2,6), 125.13 (2', 6'), 126.19, 127.27, 127.48 (2*Ctrans, 4'), 127.31 (3', 5'), 136.32 (1'), 138.52 (1), 157.28 (3, 5); LRESI positive ion mass spectrum; m/z 213 (MH+, 100%), 214 (18%); HRESI positive ion mass spectrum; C14H12O2Na+; calc. 235.0735, measured 235.0729. | |
With sodium hydroxide In dichloromethane at 20℃; for 2.5h; Inert atmosphere; Cooling with ice; | Preparation of (E)-5-[2-(3, 5-Dibromo-4-hydroxy-phenyl)-vinyl]-phenol (Compound 4z) General procedure: Acetic acid 4-[2-(3,5-dibromo-4-methoxy-phenyl)-vinyl]-phenyl ester (33 mg, 0.077 mmol) was diluted in dichloromethane (1.0 mL) and added 1.0 M dichloromethane solution of boron tribromide (0.23 mL, 0.23 mmol) under nitrogen and ice cooling. The mixture was stirred at room temperature for 2.5 h. The reaction mixture was added to cooled water under ice cooling, and extracted with ethyl acetate. The combined organic layer was washed with water and brine, then dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (20% ethyl acetate in n-hexane) to give the desire compound 4z as a white powder (26 mg, 91%). |
Yield | Reaction Conditions | Operation in experiment |
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Multi-step reaction with 2 steps 1: dichloro bis(acetonitrile) palladium(II); sodium carbonate; oxygen / N,N-dimethyl-formamide / 18 h / 50 °C 2: boron tribromide / dichloromethane / 24 h / -10 - 20 °C / Inert atmosphere |
Yield | Reaction Conditions | Operation in experiment |
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83% | With L234Q/I238V/G239A In dimethyl sulfoxide at 20℃; for 20h; Enzymatic reaction; regioselective reaction; | |
With unspecific peroxygenase from Marasmius rotula DSM-25031; dihydrogen peroxide; ascorbic acid In aq. phosphate buffer; acetone at 30℃; for 0.5h; Enzymatic reaction; regioselective reaction; |