Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid; iron(III) perchlorate In acetonitrile at -10℃; for 0.0833333h; | 100% |
With sodium periodate; 5-Nitro-1,10-phenanthroline; iron(II) sulfate In dichloromethane; water at 20℃; for 20h; | 100% |
With (5,10,15,20-tetrakis(p-methoxyphenyl)-21H,23H-porphyrinate)cobalt(II); oxygen; isobutyraldehyde In acetonitrile for 3h; Ambient temperature; | 100% |
Conditions | Yield |
---|---|
With sodium chlorite; edetate disodium In water; acetonitrile at 55 - 65℃; for 14h; | 100% |
With urea hydrogen peroxide adduct; ruthenium(2,2',6':2''-terpyridine)(2,6-pyridinedicarboxylate) In tert-Amyl alcohol at 20℃; for 1h; Product distribution; Further Variations:; Catalysts; Reagents; | 99% |
With Oxone; ethylenediaminetetraacetic acid; sodium carbonate In water; acetonitrile at 0 - 20℃; for 6h; | 98% |
benzaldehyde
dimethyl<(phenyl)trimethylsilylmehyl>sulfoniumtrifluoromethanesulfonate
trans-Stilbene oxide
Conditions | Yield |
---|---|
With cesium fluoride In 1,2-dimethoxyethane at 45℃; for 18h; | 98% |
Conditions | Yield |
---|---|
With thiophene; N-benzyl-N,N,N-triethylammonium chloride; dirhodium tetraacetate In acetonitrile at 40℃; for 24h; | A n/a B 98% |
Conditions | Yield |
---|---|
With hydrotris(3,4,5-tribromopyrazolyl)borate Cu (NCMe); dimethylsulfide In dichloromethane; toluene at 20℃; for 2h; Catalytic behavior; Reagent/catalyst; Solvent; Inert atmosphere; diastereoselective reaction; | 95% |
With copper acetylacetonate; ethyl isopropyl sulfide In dichloromethane | 73% |
sodium 2-benzylidene-1-tosylhydrazin-1-ide
benzaldehyde
trans-Stilbene oxide
Conditions | Yield |
---|---|
With thiophene; dirhodium tetraacetate; N-benzyl-N,N,N-triethylammonium chloride In acetonitrile at 40℃; for 3h; | 95% |
Conditions | Yield |
---|---|
With 1H-imidazole; chloro(meso-tetrakis(2,6-dichlorophenyl)porphyrinato)manganese(III); dihydrogen peroxide In dichloromethane; acetonitrile for 2h; Ambient temperature; | A 94% B 3% |
With 1H-imidazole; manganese(III) meso-tetraphenylporphyrin acetate; tetrabutylammonium periodite In dichloromethane; tert-butyl alcohol at 22℃; for 5h; Inert atmosphere; | A 92% B 3% |
With oxygen In water at 25℃; under 760.051 Torr; for 4h; | A n/a B 92% |
cis-stilben
A
phenyl benzyl ketone
B
cis-1,2-diphenyloxirane
trans-Stilbene oxide
Conditions | Yield |
---|---|
With 1H-imidazole; dihydrogen peroxide; Mn(TDCPP)Cl In dichloromethane; acetonitrile for 0.25h; Ambient temperature; | A 2% B 92% C 2% |
With tert.-butylhydroperoxide In water; acetonitrile at 85℃; for 24h; Catalytic behavior; | A 7.2 %Chromat. B 42.3% C 8.3% |
With O(3P) prepared by O2 discharge at 0℃; for 0.5h; | A 29% B 31% C 40% |
Conditions | Yield |
---|---|
With [bis(acetoxy)iodo]benzene; ruthenium(2,2',6':2''-terpyridine)(2,6-pyridinedicarboxylate) In dichloromethane for 72h; Ambient temperature; | A n/a B 92% |
With oxygen; isobutyraldehyde; 4 In water; 1,2-dichloro-ethane at 40℃; for 72h; | A 15% B 83% |
With pyridine N-oxide; oxochromium(V) complex of tetramethylsalen IIb In acetonitrile | A 10% B 81% |
Conditions | Yield |
---|---|
With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; | 91% |
With Perbenzoic acid; chloroform | |
With 3-chloro-benzenecarboperoxoic acid |
1-benzyl-3-methylbenzotriazolium iodide
benzaldehyde
trans-Stilbene oxide
Conditions | Yield |
---|---|
With potassium tert-butylate In dimethyl sulfoxide; tert-butyl alcohol at 20℃; optical yield given as %de; diastereoselective reaction; | A 90% B 70% |
Conditions | Yield |
---|---|
With triphenyl-arsane; N-benzyl-N,N,N-triethylammonium chloride; dirhodium tetraacetate In acetonitrile at 40℃; | 89% |
Conditions | Yield |
---|---|
With dimethyl sulfoxide; sodium hydroxide at 20℃; for 4h; Reagent/catalyst; | 89% |
With (1R,2R,4R)-(+)-isobornyl methyl sulfide; sodium hydroxide In acetonitrile for 72h; | 50% |
cyclic sulfate of meso-hydrobenzoin
trans-Stilbene oxide
Conditions | Yield |
---|---|
With sodium hydroxide In tetrahydrofuran; methanol at 20℃; for 1h; | 86% |
Conditions | Yield |
---|---|
With dihydrogen peroxide; iron(III) perchlorate In acetonitrile Product distribution; Heating; other oxidant, other catalysts; | A 85% B 15% |
With 2MnIVTPP; 5,15,10,20-tetraphenylporphyrin In chlorobenzene at 25℃; | A n/a B 37% |
With pyridine; sodium hypochlorite; benzyldimethyltetradecylammonium chloride; [MnIII(TPP)(OAc)] In dichloromethane; water for 5h; Ambient temperature; Yields of byproduct given; | A n/a B 20% |
Conditions | Yield |
---|---|
With trifluoromethylsulfonic anhydride; polymer-supported triphenylphosphine oxide; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; | 85% |
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; | 85% |
With diethoxyltriphenylphosphorane In toluene at 100℃; for 18h; |
Conditions | Yield |
---|---|
With dimethyl sulfoxide; sodium hydroxide at 20℃; for 12h; Reagent/catalyst; | 85% |
With dimethyl sulfoxide; silver(l) oxide at 20℃; Inert atmosphere; | 48% |
Multi-step reaction with 3 steps 1: 1.) n-butyllithium / 1.) ether, -20 deg C, 1 h., 2.) ether 2: 100 percent / benzene / 0 °C 3: 80 percent / flame-dried cesium fluoride / 1,2-dimethoxy-ethane / 12 h / 40 °C View Scheme |
Conditions | Yield |
---|---|
In acetonitrile at 22℃; Corey-Chaikovsky reaction; Electrolysis; | 83% |
benzaldehyde
methyl (phenylmethyl)<(trimethylsilyl)methyl>sulfonium trifluoromethanesulfonate
trans-Stilbene oxide
Conditions | Yield |
---|---|
With cesium fluoride In 1,2-dimethoxyethane at 40℃; for 12h; | 80% |
(1S,2R)-1,2-diphenylethane-1,2-diol
p-toluenesulfonyl chloride
trans-Stilbene oxide
Conditions | Yield |
---|---|
With triethylamine; di(n-butyl)tin oxide In dichloromethane at 20℃; for 0.666667h; | A 5% B 80% |
With di(n-butyl)tin oxide; triethylamine In dichloromethane at 20℃; for 0.666667h; Tosylation; |
1-benzyltetrahydro-1H-thiophen-1-ium bromide
benzyl alcohol
trans-Stilbene oxide
Conditions | Yield |
---|---|
With barium manganate; 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In acetonitrile at 60℃; for 1h; Corey-Tschaikosky Epoxidation; | 78% |
Stage #1: benzyl alcohol With manganese(IV) oxide In chloroform for 2h; Reflux; Stage #2: 1-benzyltetrahydro-1H-thiophen-1-ium bromide With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In chloroform for 0.333333h; | 68% |
cis-stilben
A
benzaldehyde
B
cis-1,2-diphenyloxirane
trans-Stilbene oxide
Conditions | Yield |
---|---|
With meso-tetrakis(pentafluorophenyl)porphirinato Fe(IV) nitrate; dihydrogen peroxide In dichloromethane; acetonitrile at 20℃; for 0.166667h; Product distribution; Further Variations:; Reagents; Epoxidation; Oxidation; | A 3% B 74% C 3% |
With Ni(N-(2-pyridylmethyl)-N’-(2-hydroxyethyl)ethylenediamine)(N3)2; 3-chloro-benzenecarboperoxoic acid In dichloromethane; acetonitrile at 20℃; for 0.166667h; | A 16.1% B 6.8% C 64.6% |
With iodosylbenzene; tetraphenylporphyrine aluminum chloride In toluene for 24h; Ambient temperature; | A 0.0008 mmol B 62% C 0.005 mmol |
(+/-)-trans-5,6-diphenyl-1,4-dioxane-2,3-dione
trans-Stilbene oxide
Conditions | Yield |
---|---|
In acetonitrile for 0.5h; Irradiation; | 73% |
C18H20Cl2O
trans-Stilbene oxide
Conditions | Yield |
---|---|
With potassium tert-butylate In dimethyl sulfoxide at 25℃; for 0.75h; | 70% |
erythro-1,2-Diphenyl-1,2-ethanediol
trans-Stilbene oxide
Conditions | Yield |
---|---|
With sodium hydroxide; methanesulfonyl chloride; N-benzyl-N,N,N-triethylammonium chloride In dichloromethane for 0.5h; Heating; | 70% |
Conditions | Yield |
---|---|
With phenyllithium | A 7% B 66% |
Conditions | Yield |
---|---|
With sodium hydroxide; Aliquat 336 In dichloromethane at 0℃; for 24h; Product distribution; other sulfonium salts and aldehydes; also without phase transfer catalyst; | A 6% B 66% |
Conditions | Yield |
---|---|
With potassium tert-butylate In dimethyl sulfoxide; tert-butyl alcohol at 20℃; optical yield given as %de; diastereoselective reaction; | A n/a B n/a C 66% |
(E)-1,2-diphenyl-ethene
A
benzaldehyde
B
cis-1,2-diphenyloxirane
trans-Stilbene oxide
Conditions | Yield |
---|---|
With Ni(N-(2-pyridylmethyl)-N’-(2-hydroxyethyl)ethylenediamine)(N3)2; 3-chloro-benzenecarboperoxoic acid In dichloromethane; acetonitrile at 20℃; for 0.166667h; | A 17.8% B 9.4% C 64.5% |
With iodosylbenzene; tetraphenylporphyrine aluminum chloride In toluene for 24h; Ambient temperature; | A 0.002 mmol B 0.003 mmol C 6.4% |
With tert.-butylhydroperoxide; molecular sieve In Petroleum ether for 24h; Ambient temperature; | A 0.27 % Spectr. B 0.18 % Spectr. C 9.35 % Spectr. |
With Ru(VI)(octaethylporphyrin)(O)2 In dichloromethane for 24h; Yield given. Yields of byproduct given; | |
With iodoxybenzene; bis(acetylacetonato) oxovanadium(IV) In benzene for 4h; Product distribution; | A 38 % Chromat. B 10 % Chromat. C 13 % Chromat. |
(E)-1,2-diphenyl-ethene
A
styrene oxide
B
benzoic acid
trans-Stilbene oxide
Conditions | Yield |
---|---|
With tetrachloromethane; 18-crown-6 ether In acetonitrile at 10℃; | A 11% B 11% C 62% |
sodium methylate
trans-Stilbene oxide
erythro-2-methoxy-1,2-diphenylethanol
Conditions | Yield |
---|---|
In methanol for 108h; Heating; | 100% |
Conditions | Yield |
---|---|
With <(n-C4H9)3SnAl(C2H5)3>(1-)*Li(1+) In tetrahydrofuran; hexane at 25℃; for 24h; Product distribution; (C6H5)(CH3)2SiAl(C2H5)2 as deoxygenation reagent; | 100% |
With vanadium monochloride In tetrahydrofuran at 25℃; for 12h; Inert atmosphere; | 100% |
With n-Bu3Sn-AlMe3Li In tetrahydrofuran; hexane at 25℃; for 3h; | 98% |
Conditions | Yield |
---|---|
With lithium bromide at 150℃; for 4h; | 100% |
piperidine
trans-Stilbene oxide
1,2-diphenyl-2-(piperidin-1-yl)ethanol
Conditions | Yield |
---|---|
bismuth(lll) trifluoromethanesulfonate at 160℃; for 0.25h; microwave irradiation; | 100% |
Conditions | Yield |
---|---|
With erbium(III) triflate In dichloromethane at 20℃; for 0.75h; | 99% |
With trimethylaluminum; 1,3-bis(3-t-butyl-5-methylsalicyl)benzene In dichloromethane Ambient temperature; | 98% |
With copper(II) tetrafluoroborate hydrate In dichloromethane for 1.5h; Meinwald rearrangement; Reflux; regioselective reaction; | 95% |
trans-Stilbene oxide
1,2-Diphenylethanol
Conditions | Yield |
---|---|
With formic acid; triethylamine; Pd0-EnCatTM In ethyl acetate at 23℃; for 5h; | 99% |
With ammonium formate In ethyl acetate at 25℃; for 24h; Inert atmosphere; | 99% |
With hydrogen; Pd/magnetite In ethyl acetate at 23℃; under 760.051 Torr; for 0.5h; | 94% |
Conditions | Yield |
---|---|
at 90℃; for 3h; | 99% |
cyclohexylamine
trans-Stilbene oxide
2-(cyclohexylamino)-1,2-diphenylethanol
Conditions | Yield |
---|---|
bismuth(lll) trifluoromethanesulfonate at 160℃; for 0.25h; microwave irradiation; | 99% |
trans-Stilbene oxide
trans-2,3-diphenylthiirane
Conditions | Yield |
---|---|
With Dowex-50WX8-supported thiourea for 0.0166667h; Microwave irradiation; neat (no solvent); | 98% |
With ammonium chloride; thiourea at 60 - 70℃; for 0.75h; neat (no solvent); | 96% |
With thiourea In methanol for 0.3h; Molecular sieve; Reflux; | 95% |
With indium(III) bromide; potassium thioacyanate In acetonitrile at 60℃; for 3h; | 93% |
With ammonium thiocyanate at 60℃; for 2h; Neat (no solvent); | 90% |
carbon dioxide
trans-Stilbene oxide
(4R,5R)-4,5-diphenyl-1,3-dioxolan-2-one
Conditions | Yield |
---|---|
With [La{N(SiHMe2)2}2{k3-2,2-bis(3,5-dimethylpyrazol-1-yl)-1,1-diphenylethylcyclopentadienyl}]; tetrabutylammomium bromide In neat (no solvent) at 90℃; under 7500.75 Torr; for 18h; | 98% |
With C30H41Al2N5S; tetrabutylammomium bromide In neat (no solvent) at 90℃; under 7500.75 Torr; for 16h; stereoselective reaction; | 93% |
With C30H34BrCrN2O4; tetrabutylammomium bromide In neat (no solvent) at 80℃; under 7500.75 Torr; for 24h; Temperature; | 89% |
trans-Stilbene oxide
trimethyl orthoformate
2,2-diphenylacetaldehyde dimethyl acetal
Conditions | Yield |
---|---|
With mesoporous aluminosilicate catalyst, Si/Al ratio = 14:1 In chloroform at 20 - 55℃; | 98% |
Conditions | Yield |
---|---|
With (S,S)-(+)-N,N'-bis(3,5-di-tert-butylsalicylidene)-1,2-cyclohexanediamino chromium(III) chloride at 20℃; for 4h; Ionic liquid; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | A n/a B 98% |
allyltributylstanane
trans-Stilbene oxide
Conditions | Yield |
---|---|
ytterbium(III) triflate In tetrahydrofuran at 60℃; for 22h; | 96% |
2,6-dimethylphenyl isonitrile
trans-Stilbene oxide
Conditions | Yield |
---|---|
With gallium(III) trichloride In diethyl ether; dichloromethane at 40℃; for 2h; | 96% |
orthoformic acid triethyl ester
trans-Stilbene oxide
2,2-diphenylacetaldehyde diethyl acetal
Conditions | Yield |
---|---|
With mesoporous aluminosilicate catalyst, Si/Al ratio = 14:1 In chloroform at 20 - 55℃; | 96% |
Conditions | Yield |
---|---|
With Amberlyst 15; sodium iodide In acetone at 20℃; for 3h; deoxygenation; | 95% |
With lithium; di-o-anisylphosphinyl chloride; methyl iodide 1.) THF, 4.5 h, 2.) THF, RT; 1 h; Yield given. Multistep reaction; | |
Multi-step reaction with 3 steps 1: NaH / acetonitrile / 24 h / 20 °C 2: Oxone / methanol; H2O / 24 h / 20 °C 3: KOH; tetrabutylammonium bromide / tetrahydrofuran / 16 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: 1.) n-BuLi / 1.) THF, room t., 2.) THF, room t. 2: t-BuOK / CD3CN / -10 °C View Scheme | |
Multi-step reaction with 3 steps 1: 75 percent / KOH / propan-1-ol / 8 h / Heating 2: 75 percent / m-chloroperoxybenzoic acid / CH2Cl2 3: 51 percent / N-chlorosuccinimide / benzene / 1 h / Heating View Scheme |
lithium diphenylphosphide
trans-Stilbene oxide
(1RS,2SR)-1,2-diphenyl-2-diphenylphosphinoylmethan-1-ol
Conditions | Yield |
---|---|
In tetrahydrofuran | 93% |
trans-Stilbene oxide
(±)-trans-2-bromo-1,2-diphenylethan-1-ol
Conditions | Yield |
---|---|
With magnesium bromide In diethyl ether at 0℃; for 4h; | 92% |
With diethyl ether; hydrogen bromide |
Conditions | Yield |
---|---|
With triethylamine In methanol for 18h; 0 deg C to r.t.; | 92% |
2-buten-4-olide
trans-Stilbene oxide
2,4-Diphenyl-3,7-dioxabicyclo<3.3.0>octan-8-one
Conditions | Yield |
---|---|
With naphthalene-1,4-dicarbonitrile In acetonitrile Irradiation; | 92% |
With naphthalene-1,4-dicarbonitrile In acetonitrile Irradiation; | 90% |
The trans-Stilbene oxide, with the CAS registry number 1439-07-2, is also called trans-α,α'-Epoxybibenzyl. It is a kind of white to light yellow crystal powder, and belongs to the following product categories: Chiral; Oxiranes; Simple 3-Membered Ring Compounds. And the molecular formula of the chemical is C14H12O.
The characteristics of this chemical are as followings: (1)ACD/LogP: 3.39; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.39; (4)ACD/LogD (pH 7.4): 3.39; (5)ACD/BCF (pH 5.5): 220.53; (6)ACD/BCF (pH 7.4): 220.53; (7)ACD/KOC (pH 5.5): 1656.03; (8)ACD/KOC (pH 7.4): 1656.03; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 12.53 Å2; (13)Index of Refraction: 1.608; (14)Molar Refractivity: 59.71 cm3; (15)Molar Volume: 172.6 cm3; (16)Polarizability: 23.67×10-24cm3; (17)Surface Tension: 46.7 dyne/cm; (18)Density: 1.136 g/cm3; (19)Flash Point: 133.4 °C; (20)Enthalpy of Vaporization: 52.31 kJ/mol; (21)Boiling Point: 304.5 °C at 760 mmHg; (22)Vapour Pressure: 0.00157 mmHg at 25°C.
You should be cautious while dealing with this chemical. It is a kind of flammable chemical, and irritates to eyes, respiratory system and skin. Therefore, you should not breathe dust and then try to avoid contacting with skin and eyes.
Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: O2C(c1ccccc1)C2c3ccccc3
(2)InChI: InChI=1/C14H12O/c1-3-7-11(8-4-1)13-14(15-13)12-9-5-2-6-10-12/h1-10,13-14H
(3)InChIKey: ARCJQKUWGAZPFX-UHFFFAOYAV
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