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inquiryProduct Name: 1,1-DIPHENYL-2-PROPYN-1-OL Synonyms: 1,1-diphenyl-2-propyn-1-o;1,1-Diphenylpropargyl alcohol;1,1-diphenylpropargylalcohol;2-Propyn-1-ol, 1,1-diphenyl-;3,3-Diphenyl-3-hydroxy-1-propyne;alpha-ethynyl-alpha-phenyl-b
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Conditions | Yield |
---|---|
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran; hexane at -10℃; for 0.5h; Inert atmosphere; Stage #2: benzophenone at -10 - 20℃; for 4h; Stage #3: With potassium hydroxide In methanol for 0.5h; | 100% |
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran; hexane at -10℃; for 1h; Inert atmosphere; Stage #2: benzophenone In tetrahydrofuran; hexane at -10 - 0℃; for 3h; Inert atmosphere; Stage #3: With sodium hydroxide In tetrahydrofuran; methanol; hexane at 0 - 20℃; Inert atmosphere; | 96% |
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran; hexane at -10℃; for 1h; Inert atmosphere; Stage #2: benzophenone In tetrahydrofuran; hexane for 4h; Inert atmosphere; Stage #3: With potassium hydroxide In tetrahydrofuran; methanol; hexane at 20℃; for 0.5h; | 92% |
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol at 0 - 5℃; for 0.5h; Inert atmosphere; Large scale; | 99.2% |
Stage #1: acetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: benzophenone In tetrahydrofuran; hexane at -78 - 20℃; | 96% |
With sodium hydroxide; tetrabutylammomium bromide In toluene for 2h; Ambient temperature; | 90% |
1,1-diphenyl-3-(trimethylsilyl)prop-2-yn-1-ol
1,1-diphenyl-2-propyn-1-ol
Conditions | Yield |
---|---|
With potassium carbonate In methanol at 20℃; for 2h; Inert atmosphere; | 99% |
With methanol; potassium carbonate In tetrahydrofuran | 80% |
With potassium carbonate In methanol for 12h; Yield given; |
Conditions | Yield |
---|---|
In tetrahydrofuran at 23 - 25℃; for 4h; Inert atmosphere; | 94% |
In tetrahydrofuran at -78 - 20℃; for 20h; Inert atmosphere; | 93% |
In tetrahydrofuran Heating; | 75% |
Conditions | Yield |
---|---|
In tetrahydrofuran; xylene at -10 - 20℃; | 88% |
With ammonia | |
In ammonia |
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride; water In dimethyl sulfoxide at 20℃; for 5h; Inert atmosphere; | 53% |
benzophenone
A
1,1,4,4-tetraphenyl-2-butyne-1,4-diol
B
1,1-diphenyl-2-propyn-1-ol
Conditions | Yield |
---|---|
Stage #1: calcium carbide With potassium hydroxide for 0.5h; Favorskii Rearrangement; Milling; Sealed tube; Stage #2: benzophenone for 3h; Reagent/catalyst; Favorskii Rearrangement; Milling; Sealed tube; | A 41% B 25% |
ethynyldimagnesium dibromide
benzophenone
diethyl ether
A
1,1,4,4-tetraphenyl-2-butyne-1,4-diol
B
1,1-diphenyl-2-propyn-1-ol
Conditions | Yield |
---|---|
at -10℃; |
benzophenone
A
1,1,4,4-tetraphenyl-2-butyne-1,4-diol
B
1,1-diphenyl-2-propyn-1-ol
Conditions | Yield |
---|---|
With potassium hydroxide; diethyl ether Einleiten von Acetylen; |
Conditions | Yield |
---|---|
With potassium carbonate at 170℃; unter vermindertem Druck; |
benzophenone
lithium acetylide-ethylenediamine complex
1,1-diphenyl-2-propyn-1-ol
Conditions | Yield |
---|---|
With acetylene In N,N-dimethyl acetamide at 25℃; for 1.75h; |
Carbamidsaeure-<1,1-diphenyl-propin-(2)-ylester>
1,1-diphenyl-2-propyn-1-ol
Conditions | Yield |
---|---|
With sodium hydroxide In ethanol |
benzophenone
A
1,1,4,4-tetraphenyl-2-butyne-1,4-diol
B
1,1-diphenyl-2-propyn-1-ol
Conditions | Yield |
---|---|
anschliessendes Behandeln mit Aethanol; |
benzophenone
ammonia
sodium acetylide
1,1-diphenyl-2-propyn-1-ol
benzophenone
ammonia
potassium acetylide
A
1,1,4,4-tetraphenyl-2-butyne-1,4-diol
B
1,1-diphenyl-2-propyn-1-ol
1,1,4,4-tetraphenyl-2-butyne-1,4-diol
A
benzophenone
B
1,1-diphenyl-2-propyn-1-ol
Conditions | Yield |
---|---|
at 170℃; unter vermindertem Druck; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: n-BuLi / tetrahydrofuran; hexane / 1.) -70 deg C, 5 min, 2.) reflux, 12 h 2: K2CO3 / methanol / 12 h View Scheme |
C33H26OSi
1,1-diphenyl-2-propyn-1-ol
Conditions | Yield |
---|---|
With tetrabutyl ammonium fluoride In tetrahydrofuran at 0℃; for 3h; |
benzophenone
lithium trimethylsilylacetylenide
1,1-diphenyl-2-propyn-1-ol
Conditions | Yield |
---|---|
Stage #1: benzophenone; lithium trimethylsilylacetylenide In tetrahydrofuran at -78 - -20℃; Stage #2: With water; ammonium chloride In tetrahydrofuran |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -70 °C / Inert atmosphere 1.2: 1 h / -70 - 20 °C / Inert atmosphere 2.1: methanol; potassium carbonate / 2 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 10 °C / Inert atmosphere 1.2: 3 h / Inert atmosphere 2.1: potassium hydroxide / tetrahydrofuran; methanol; hexane / 0 - 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: n-butyllithium / tetrahydrofuran / Inert atmosphere 2: potassium hydroxide / methanol / Inert atmosphere View Scheme | |
Multi-step reaction with 2 steps 1.1: n-butyllithium / tetrahydrofuran / 1.2 h / -78 °C / Inert atmosphere 1.2: -78 - 20 °C 2.1: potassium carbonate / methanol / 2 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1.1: n-butyllithium / diethyl ether / -10 °C / Inert atmosphere 1.2: -10 - 20 °C 2.1: potassium carbonate / methanol; tetrahydrofuran View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: aluminum (III) chloride / dichloromethane / Inert atmosphere 2: n-butyllithium / tetrahydrofuran / Inert atmosphere 3: potassium hydroxide / methanol / Inert atmosphere View Scheme |
O-(trimethylsilyl)-1,1-diphenyl-2-propyn-1-ol
1,1-diphenyl-2-propyn-1-ol
Conditions | Yield |
---|---|
With potassium carbonate In methanol at 20℃; for 2h; |
benzophenone
calcium carbide
A
1,1,4,4-tetraphenyl-2-butyne-1,4-diol
B
1,1-diphenyl-2-propyn-1-ol
Conditions | Yield |
---|---|
In neat (no solvent) for 0.666667h; Milling; Sealed tube; Overall yield = 75 percent; |
Conditions | Yield |
---|---|
With sulfuric acid In 1,4-dioxane; water for 0.0833333h; Meyer-Schuster rearrangement; Heating; | 100% |
With silver(I) tetrakis(3,5-bis(trifluoromethyl)phenyl)borate In water; ethyl acetate at 80℃; for 24h; Meyer-Schuster Rearrangement; Sealed tube; Green chemistry; chemoselective reaction; | 97% |
With ReOCl3(SMe2)(OPPh3) In 1,2-dimethoxyethane at 80℃; for 20h; Meyer-Schuster rearrangement; | 96% |
Conditions | Yield |
---|---|
Rh(acac)(cyclooctene)(PCy3) In benzene-d6 Ar-atmosphere; 48 h at room temp.; | 100% |
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran for 12h; Sonogashira Cross-Coupling; Inert atmosphere; Reflux; | 100% |
(1,1-dimethylethyl)(3-iodophenoxy)dimethylsilane
1,1-diphenyl-2-propyn-1-ol
3-[3-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-1,1-diphenyl-prop-2-yn-1-ol
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine In dichloromethane for 18h; Heating; | 99.7% |
trimethylsilyl trifluoromethanesulfonate
1,1-diphenyl-2-propyn-1-ol
O-(trimethylsilyl)-1,1-diphenyl-2-propyn-1-ol
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0℃; for 0.416667h; | 99% |
silver(I) hexafluorophosphate
1,1-diphenyl-2-propyn-1-ol
Conditions | Yield |
---|---|
In tetrahydrofuran stirring (40 min), evapn.; extg. (CH2Cl2), filtering, concg., pptn. on hexane addn., filtering, washing (hexane), drying (vac.); elem. anal.; | 99% |
1-Azidoadamantane
1,1-diphenyl-2-propyn-1-ol
(1-adamantyl-1H-1,2,3-triazol-4-yl)diphenylmethanol
Conditions | Yield |
---|---|
With 2,6-dimethylpyridine In water at 20℃; for 24h; Huisgen 1,3-dipolar cycloaddition; regioselective reaction; | 99% |
(E)-5-trifluoromethanesulfonyloxymethylidene-1-cyclopenten-1-yl trifluoromethanesulfonate
1,1-diphenyl-2-propyn-1-ol
1,1-diphenyl-3-<(E)-5-(4,4-diphenyl-4-hydroxy-2-butynylidene)-1-cyclopenten-1-yl>-2-propyn-1-ol
Conditions | Yield |
---|---|
With diethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In N,N-dimethyl-formamide Ambient temperature; | 98% |
With copper(l) iodide; Pd2Cl(PPh3)2; diethylamine In N,N-dimethyl-formamide for 3h; Ambient temperature; | 96% |
1,1-diphenyl-2-propyn-1-ol
β-naphthol
3,3-diphenyl-3H-naphtho[2,1-b]pyran
Conditions | Yield |
---|---|
With sodium hydroxide; toluene-4-sulfonic acid In hexane; benzene | 98% |
With sodium hydroxide; toluene-4-sulfonic acid In hexane; benzene | 98% |
With sodium hydroxide; toluene-4-sulfonic acid In hexane; benzene | 98% |
1,1-diphenyl-2-propyn-1-ol
Conditions | Yield |
---|---|
In tetrahydrofuran addn. of the alkyne in THF to a THF soln. of the Ru-compd., stirring overnight at room temp.; removal of solvent, washing of resultant solid with hexane, chromy. on silica gel with THF, evapn. of solvent; | 98% |
dichlorotris(triphenylphosphine)osmium(II)
1,1-diphenyl-2-propyn-1-ol
Conditions | Yield |
---|---|
In toluene (N2); stirring (reflux, 3 h); solvent removal (reduced pressure), redissoln. (CH2Cl2), slow addn. of hexane, filtration, washing (hexane), drying (vac.); elem. anal.; | 98% |
Conditions | Yield |
---|---|
Stage #1: 1,1-diphenyl-2-propyn-1-ol With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 0.666667h; Inert atmosphere; Stage #2: methyl iodide With dimethyl sulfoxide In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere; | 98% |
1,1-diphenyl-2-propyn-1-ol
Conditions | Yield |
---|---|
In methanol under Ar; Ru complex dissolved in MeOH; Ph2C(OH)CCH (excess) added; stirred for 1 min; NaPF6 added; refluxed for 24 h; filtered; solvent removed in vac.; treated with Et2O and n-hexane; ppt. collected; elem. anal.; | 98% |
Conditions | Yield |
---|---|
With sodium azide; sodium L-ascorbate In water at 90℃; for 0.5h; Huisgen Cycloaddition; Green chemistry; regioselective reaction; | 98% |
With sodium azide; [CuI(3,7-diacetyl-1,3,7-triaza-5-phosphabicyclo[3.3.1]nonane)3] In water; acetonitrile at 125℃; for 0.25h; Catalytic behavior; Huisgen Cycloaddition; Sealed tube; Microwave irradiation; | 81% |
With sodium azide; [(tris(3,5-dimethyl-1-pyrazolyl)methane)2Cu](BF4)2 In methanol; water at 125℃; for 0.5h; Catalytic behavior; Microwave irradiation; | 78% |
Conditions | Yield |
---|---|
With copper(ll) sulfate pentahydrate In dichloromethane at 20℃; for 24h; | 98% |
1,1-diphenyl-2-propyn-1-ol
thieno[3,2-b]pyridin-3(2H)-one
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In acetonitrile for 1h; Inert atmosphere; Reflux; | 98% |
1,1-diphenyl-2-propyn-1-ol
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide at 80℃; for 8h; Inert atmosphere; | 98% |
(carbonyl)(chloro)(hydrido)tris(triphenylphosphine)ruthenium(II)
1,1-diphenyl-2-propyn-1-ol
RuCl(CO)(CHCHC(C6H5)2OH)(P(C6H5)3)2
Conditions | Yield |
---|---|
97% |
1,1-diphenyl-2-propyn-1-ol
Conditions | Yield |
---|---|
In dichloromethane Ar; stirred at room temp. for 4 h; solvent distilled (vac.); | 97% |
Conditions | Yield |
---|---|
With 2,6-dimethylpyridine; C21H26N4O4P2S*F6P(1-)*Cu(1+) In water at 20℃; for 7h; | 97% |
Conditions | Yield |
---|---|
Stage #1: diazoacetic acid ethyl ester; 1,1-diphenyl-2-propyn-1-ol With copper(l) iodide In acetonitrile at 25℃; Stage #2: With triethylamine In dichloromethane at 0℃; for 1h; | 97% |
1-(azidomethyl)-4-methoxybenzene
1,1-diphenyl-2-propyn-1-ol
Conditions | Yield |
---|---|
With copper(II) sulfate pentahydrate; sodium L-ascorbate In dichloromethane; water at 20℃; for 5h; | 97% |
ethyl 1-hydroxy-4-phenylnaphthalene-3-carboxylate
1,1-diphenyl-2-propyn-1-ol
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate; trimethyl orthoformate In 1,2-dichloro-ethane Heating; | 96% |
With pyridinium p-toluenesulfonate; trimethyl orthoformate In 1,2-dichloro-ethane Reflux; | 24% |
chloridogold(I)[tri[1,3,5-triaza-7-phosphaadamantane]phosphane]
1,1-diphenyl-2-propyn-1-ol
[Au(C2CPh2OH)(1,3,5-triaza-7-phosphaadamantane)]
Conditions | Yield |
---|---|
With NaOC2H5 In ethanol to a soln. of NaOC2H5 in ethanol was added Au-complex and alkyne, the mixt. was allowed to stir at room temp. overnight; filtered, ppt. was wasehd with water, ethanol and pentane; elem. anal.; | 96% |
Conditions | Yield |
---|---|
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine In tetrahydrofuran at 50℃; for 3h; Sonogashira Cross-Coupling; Inert atmosphere; | 96% |
acetic anhydride
1,1-diphenyl-2-propyn-1-ol
1,1-diphenyl-2-propyn-1-yl acetate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane for 16h; Reflux; Inert atmosphere; | 95% |
With dmap; triethylamine | 72% |
With sodium hydroxide; diethyl ether |
Phenylselenyl chloride
1,1-diphenyl-2-propyn-1-ol
E-2-chloro-3-phenylseleno-1,1-diphenyl-2-propen-1-ol
Conditions | Yield |
---|---|
In dichloromethane Ambient temperature; | 95% |
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