Conditions | Yield |
---|---|
With hydrogenchloride; water at 0 - 20℃; for 1.25h; Inert atmosphere; | 96% |
With hydrogenchloride In water at 0 - 20℃; for 1.5h; | 93% |
With hydrogenchloride; water In water at 0 - 20℃; for 1.25h; | 87% |
tetrahydro-2H-2-pyranol
Conditions | Yield |
---|---|
With methanol; iodine; magnesium at 40℃; for 3h; | 96% |
Conditions | Yield |
---|---|
With diisobutylaluminium hydride In diethyl ether; hexane at -78℃; for 2h; Reduction; | 93% |
With diisobutylaluminium hydride In hexane; dichloromethane at -78℃; for 2h; | 91% |
With diisobutylaluminium hydride In hexane; dichloromethane at -78℃; for 0.25h; | 88% |
3,4-dihydro-2H-pyran
1,6-hexanediol
A
tetrahydro-2H-2-pyranol
B
6-(tetrahydro-2H-pyranyloxy)hexan-1-ol
C
1,6-bis(tetrahydropyranyloxy)hexane
Conditions | Yield |
---|---|
With Dowex 50W x 2 In toluene at 30℃; for 2.5h; Etherification; hydration; | A n/a B 89% C 2% |
ethyl 2-<1-(2-tetrahydropyranylperoxy)ethyl>propenoate
A
tetrahydro-2H-2-pyranol
B
n-butyl formate
Conditions | Yield |
---|---|
With tert-butyl peroxyacetate In cyclohexane at 110℃; under 0.001 Torr; for 12h; further solvents; | A 1 % Chromat. B 6 % Chromat. C 7% D 75% |
5-triphenylmethoxypentanal
tetrahydro-2H-2-pyranol
Conditions | Yield |
---|---|
Stage #1: 5-triphenylmethoxypentanal With boron trichloride In dichloromethane at -30℃; for 0.75h; Substitution; Stage #2: With methanol Cyclization; methanolysis; Further stages.; | 75% |
(E)-pent-2-ene-1,5-diol
carbon monoxide
A
tetrahydro-2H-2-pyranol
B
1 ,5-pentanediol
C
2,3,3aβ,4,5,6aβ-perhydrofuro<2,3b>furan
Conditions | Yield |
---|---|
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; hydrogen; triphenylphosphine In dichloromethane at 120℃; under 45003.6 Torr; for 20h; Product distribution; Further Variations:; Reagents; Solvents; | A n/a B n/a C 72% D n/a |
(E)-pent-2-ene-1,5-diol
carbon monoxide
A
tetrahydro-2H-2-pyranol
B
2,3,3aβ,4,5,6aβ-perhydrofuro<2,3b>furan
Conditions | Yield |
---|---|
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; hydrogen; triphenylphosphine In dichloromethane at 120℃; under 45003.6 Torr; for 20h; | A n/a B 72% |
Conditions | Yield |
---|---|
With copper(l) iodide; zinc In water ultrasonic irradiation; | 70% |
3,4,5,6-tetrahydro-2H-pyran-2-one
A
tetrahydro-2H-2-pyranol
B
5-hydroxypentanal
Conditions | Yield |
---|---|
With diisobutylaluminium hydride In dichloromethane; toluene at -70℃; for 3h; Inert atmosphere; Overall yield = 0.71 g; | A 65% B 25% |
1 ,5-pentanediol
A
tetrahydro-2H-2-pyranol
B
3,4,5,6-tetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
With 1-methyl-1H-imidazole; [2,2]bipyridinyl; tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate; 9-azabicyclo<3.3.1>nonane-N-oxyl In acetonitrile at 22℃; for 2h; | A 58% B 29% |
2-(prop-2-en-1-yloxy)oxane
trimethylaluminum
A
tetrahydro-2H-2-pyranol
Conditions | Yield |
---|---|
bis(triphenylphosphine)nickel(II) chloride In toluene | A n/a B 48% |
pent-2-ene-1,5-diol
carbon monoxide
A
tetrahydro-2H-2-pyranol
B
2,3,3aβ,4,5,6aβ-perhydrofuro<2,3b>furan
Conditions | Yield |
---|---|
With hydrogen; triphenylphosphine; chloro(1,5-cyclooctadiene)rhodium(I) dimer In 1,4-dioxane at 120℃; under 45004.5 Torr; for 20h; | A 7% B 35% C 34% |
Conditions | Yield |
---|---|
platinum In sulfuric acid; water at 35℃; for 1.15h; Product distribution; electrolysis, also with PtO2, RuO2; | 91 % Turnov. |
platinum In sulfuric acid; water at 35℃; for 1.15h; electrolysis; | 91 % Turnov. |
TETRAHYDROPYRANE
A
tetrahydro-2H-2-pyranol
B
3,4,5,6-tetrahydro-2H-pyran-2-one
Conditions | Yield |
---|---|
With 1,1,1-trifluoro-2-propanone; methyltrifluoromethyldioxirane In dichloromethane at 0℃; for 0.25h; Yield given. Yields of byproduct given; | |
lead dioxide In sulfuric acid; water at 35℃; for 7.83333h; electrolysis; | A 5.4 % Turnov. B 73 % Turnov. |
With oxone; methyltrifluoromethyldioxirane In dichloromethane at -15℃; | A 37 % Chromat. B 63 % Chromat. |
3,4-dihydro-2H-pyran
A
tetrahydro-2H-2-pyranol
B
bis-tetrahydropyran-2-yl ether
C
5-(2-tetrahydropyranyloxy)pentanal
D
5-hydroxypentanal
Conditions | Yield |
---|---|
With hydrogenchloride for 0.25h; Product distribution; Ambient temperature; other times and temperatures, other hydration reagent; | |
With hydrogenchloride; sodium sulfite at 25℃; for 24h; Yield given; | |
With hydrogenchloride at 25℃; for 0.25h; Yield given. Yields of byproduct given; |
3,4-dihydro-2H-pyran
A
tetrahydro-2H-2-pyranol
B
bis-tetrahydropyran-2-yl ether
C
5-hydroxypentanal
Conditions | Yield |
---|---|
With hydrogenchloride 1.) 25 deg C, 1 h, 2.) reflux, 24 h; Yield given. Yields of byproduct given; |
3,4-dihydro-2H-pyran
A
tetrahydro-2H-2-pyranol
B
5-(2-tetrahydropyranyloxy)pentanal
C
5-hydroxypentanal
Conditions | Yield |
---|---|
With sodium metabisulfite; water at 25℃; for 24h; Yield given. Yields of byproduct given; |
1,5-pentanedioic acid
A
tetrahydro-2H-2-pyranol
B
3,4,5,6-tetrahydro-2H-pyran-2-one
C
1 ,5-pentanediol
Conditions | Yield |
---|---|
With H4Ru4(CO)84; hydrogen In diethyl ether; toluene at 200℃; under 98800 Torr; for 48h; | A 2.9 % Chromat. B 28.7 % Chromat. C 47.7 % Chromat. D 20.7 % Chromat. |
2-phenoxytetrahydropyran
octanol
A
tetrahydro-2H-2-pyranol
B
2-octyloxy-tetrahydro-pyran
C
phenol
Conditions | Yield |
---|---|
tris(2,2'-bipyridyl)ruthenium dichloride; Paraquat In acetonitrile at 20℃; for 30h; Product distribution; Irradiation; also with H2O, or molecular sieves 4 Angstroem; |
2-phenoxytetrahydropyran
A
tetrahydro-2H-2-pyranol
B
2-octyloxy-tetrahydro-pyran
C
phenol
Conditions | Yield |
---|---|
With water; tris(2,2'-bipyridyl)ruthenium dichloride; (MV)Cl2 In acetonitrile for 30h; Irradiation; Yields of byproduct given; |
C5H9O2(1-)
tetrahydro-2H-2-pyranol
Conditions | Yield |
---|---|
Thermodynamic data; protonation, ΔG0; |
hexanal
2-Acetyl-2-methyl-5-oxo-hexanoic acid allyl ester
A
tetrahydro-2H-2-pyranol
B
3-(1-Hydroxy-hexyl)-3-methyl-heptane-2,6-dione
Conditions | Yield |
---|---|
With bis(triphenylphosphine)nickel(II) chloride; zinc In N,N-dimethyl-formamide at 40℃; for 5h; Yield given. Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
With acetylacetonatodicarbonylrhodium(l); (R,S)-binaphos; hydrogen In benzene at 60℃; under 22800 Torr; Yield given. Yields of byproduct given; | |
With acetylacetonatodicarbonylrhodium(l); (R,S)-binaphos; hydrogen In benzene at 60℃; under 22800 Torr; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
2-(prop-2-en-1-yloxy)oxane
tetrahydro-2H-2-pyranol
Conditions | Yield |
---|---|
With triethylaluminum; bis(triphenylphosphine)nickel(II) chloride In toluene |
α-bromopropionate de tetrahydropyrannyle
tetrahydro-2H-2-pyranol
Conditions | Yield |
---|---|
With sodium hydroxide; potassium dihydrogenphosphate In water at 15℃; Rate constant; Mechanism; |
tetrahydro-2H-2-pyranol
Conditions | Yield |
---|---|
With sodium hydroxide; potassium dihydrogenphosphate In water at 15℃; Rate constant; Mechanism; |
tetrahydro-2H-2-pyranol
Conditions | Yield |
---|---|
With sodium hydroxide; potassium dihydrogenphosphate In water at 15℃; Rate constant; Mechanism; |
tetrahydro-2H-2-pyranol
Conditions | Yield |
---|---|
With sodium hydroxide; potassium dihydrogenphosphate In water at 15℃; Rate constant; Mechanism; |
tetrahydro-2H-2-pyranol
Conditions | Yield |
---|---|
With sodium hydroxide; potassium dihydrogenphosphate In water at 15℃; Rate constant; Mechanism; |
Conditions | Yield |
---|---|
With triethyl borane; bis(acetylacetonate)nickel(II) In tetrahydrofuran; hexane at 20℃; for 40h; | 99% |
tetrahydro-2H-2-pyranol
2,5-dimethoxyphenol
2,5-Dimethoxy-1-(tetrahydro-2H-pyran-2-yloxy)-benzol
Conditions | Yield |
---|---|
With tributylphosphine; 1,1'-azodicarbonyl-dipiperidine In tetrahydrofuran at 0 - 20℃; for 18h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
With 2-Sulfanylpyridine; FeIIFeIII2(μ3-O)(μ2-OOCCF3)6(OH2)3 In 1,2-dichloro-ethane at 60℃; for 24h; Reagent/catalyst; | 99% |
tetrahydro-2H-2-pyranol
9-bromononan-1-ol
2-(9-bromononyloxy)tetrahydropyran
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In tetrahydrofuran at 20℃; | 99% |
tetrahydro-2H-2-pyranol
(3-bromopropyl)(methyl)sulfane
Conditions | Yield |
---|---|
Stage #1: (3-bromopropyl)(methyl)sulfane With iodine; magnesium In tetrahydrofuran Reflux; Inert atmosphere; Stage #2: tetrahydro-2H-2-pyranol In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; | 99% |
tetrahydro-2H-2-pyranol
(carbethoxyethylidene)triphenylphosphorane
(E)-7-hydroxy-2-methyl-hept-2-enoic acid ethyl ester
Conditions | Yield |
---|---|
98% | |
In benzene for 12h; Ambient temperature; | 80% |
In toluene at 90℃; for 1h; | |
In benzene Wittig Olefination; | 1.87 g |
Conditions | Yield |
---|---|
With carbon tetrabromide; triphenylphosphine at 20℃; for 16h; | 97% |
With titanium(IV) tetrabutoxide; (R)-Mandelic Acid at 20℃; for 24h; | 94% |
tetrahydro-2H-2-pyranol
benzyl alcohol
tetrahydro-2-(benzyloxy)-2H-pyran
Conditions | Yield |
---|---|
With pyrrolidine hydrochloride In toluene at 100℃; for 5h; Inert atmosphere; | 96% |
tetrahydro-2H-2-pyranol
O-(tert-butyldimethylsilanyl)hydroxylamine
5-hydroxypentanal O-tert-butyldimethylsilyloxime
Conditions | Yield |
---|---|
With magnesium sulfate In diethyl ether at 20℃; for 1h; | 94% |
tetrahydro-2H-2-pyranol
3,4-dihydro-2H-pyran
bis-tetrahydropyran-2-yl ether
Conditions | Yield |
---|---|
With N.N'-bis[3,5-bis(trifluoromethyl)phenyl]thiourea at 20℃; for 19h; | 94% |
tetrahydro-2H-2-pyranol
1-triphenylphosphoranylidene-2-propanone
(E)-8-Hydroxy-oct-3-en-2-one
Conditions | Yield |
---|---|
93% |
tetrahydro-2H-2-pyranol
4-but-1-enylmagnesium bromide
non-8-ene-1,5-diol
Conditions | Yield |
---|---|
In tetrahydrofuran for 1.5h; Ambient temperature; | 93% |
Conditions | Yield |
---|---|
With 1-methyl-pyrrolidin-2-one; Li2CuCl4 In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Schlenk technique; | 93% |
Conditions | Yield |
---|---|
With ammonium hydroxide; hydrogen In water at 80℃; under 15001.5 Torr; for 6h; Pressure; Temperature; | 93% |
With ammonia; hydrogen In water at 80℃; under 15001.5 Torr; for 1h; Reagent/catalyst; Autoclave; | |
With ammonium hydroxide; hydrogen In water at 60℃; under 15001.5 Torr; for 1h; Catalytic behavior; Temperature; Autoclave; |
tetrahydro-2H-2-pyranol
Benzeneselenol
tetrahydro-2-(phenylseleno)-2H-Pyran
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene at 25℃; | 92% |
tetrahydro-2H-2-pyranol
benzyltriphenylphosphonium chloride
6-phenylhex-5-en-1-ol
Conditions | Yield |
---|---|
Stage #1: benzyltriphenylphosphonium chloride With potassium tert-butylate In tert-butyl alcohol at 20℃; for 0.5h; Stage #2: tetrahydro-2H-2-pyranol In tert-butyl alcohol at 20℃; for 0.5h; | 92% |
Conditions | Yield |
---|---|
With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; benzoic acid In chloroform at 23℃; for 24h; Michael Addition; enantioselective reaction; | A 92% B n/a |
Stage #1: tetrahydro-2H-2-pyranol; 2-(2-nitro-vinyl)-phenol With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; benzoic acid In chloroform at 25℃; for 24h; Stage #2: With hydrogenchloride In dichloromethane; water for 2h; Overall yield = 92 %; | A n/a B n/a |
Conditions | Yield |
---|---|
In neat (no solvent) at 20℃; for 18h; Passerini Condensation; | 92% |
Conditions | Yield |
---|---|
With benzoic acid In toluene at 110℃; for 24h; Inert atmosphere; | 90% |
tetrahydro-2H-2-pyranol
n-undecyltriphenylphosphonium bromide
5-(Z,E)-hexadecenol
Conditions | Yield |
---|---|
Stage #1: n-undecyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 1h; Stage #2: tetrahydro-2H-2-pyranol In tetrahydrofuran; hexane at 0 - 20℃; Wittig reaction; | 89% |
tetrahydro-2H-2-pyranol
2-phenylethanol
2-(2-phenylethoxy)tetrahydro-2H-pyran
Conditions | Yield |
---|---|
With rhenium(VII) oxide In dichloromethane at 20℃; Time; Inert atmosphere; | 89% |
Conditions | Yield |
---|---|
In neat (no solvent) at 20℃; for 18h; Passerini Condensation; | 89% |
tetrahydro-2H-2-pyranol
(2-trimethylsilylethylidene)triphenylphosphorane
7-(trimethylsilyl)-(E,Z)-5-hepten-1-ol
Conditions | Yield |
---|---|
88% | |
In tetrahydrofuran -78 deg C to r.t.; | 80% |
tetrahydro-2H-2-pyranol
ethyl (triphenylphosphoranylidene)acetate
ethyl cis/trans-7-hydroxy-2-heptenoate
Conditions | Yield |
---|---|
In dichloromethane for 1.5h; Wittig reaction; Heating; | 88% |
85% | |
79% |
tetrahydro-2H-2-pyranol
ethyl (triphenylphosphoranylidene)acetate
ethyl (E)-7-hydroxyhept-2-enoate
Conditions | Yield |
---|---|
In tetrahydrofuran Wittig reaction; Heating; | 88% |
In dichloromethane for 48h; Ambient temperature; | 83% |
In dichloromethane at 23℃; for 96h; Inert atmosphere; | 80% |
tetrahydro-2H-2-pyranol
2-methyl-5-(phenylsulfonyl)-2-pentene
9-methyl 6-phenylsulphonyl 8-decen 1,5-diol
Conditions | Yield |
---|---|
With lithium diisopropyl amide at 20℃; for 18h; | 87% |
The 2H-Pyran-2-ol,tetrahydro- is an organic compound with the formula C5H10O2. The IUPAC name of this chemical is Oxan-2-ol. With the CAS registry number 694-54-2, it is also named as 2-Tetrahydropyranol. Besides, it is clear colorless liquid, which should be stored in a cool, sealed, dry place.
Physical properties about 2H-Pyran-2-ol,tetrahydro- are: (1)ACD/LogP: -0.36; (2)ACD/LogD (pH 5.5): -0.36; (3)ACD/LogD (pH 7.4): -0.36; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 15.15; (7)ACD/KOC (pH 7.4): 15.15; (8)#H bond acceptors: 2; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 1; (11)Polar Surface Area: 18.46 Å2; (12)Index of Refraction: 1.467; (13)Molar Refractivity: 26.25 cm3; (14)Molar Volume: 94.4 cm3; (15)Polarizability: 10.4×10-24 cm3; (16)Surface Tension: 36 dyne/cm; (17)Density: 1.08 g/cm3; (18)Flash Point: 71.4 °C; (19)Enthalpy of Vaporization: 47.37 kJ/mol; (20)Boiling Point: 170.5 °C at 760 mmHg; (21)Vapour Pressure: 0.471 mmHg at 25 °C.
Preparation: this chemical can be prepared by Tetrahydro-pyran-2-one. This reaction will need reagent diisobutylaluminum hydride (DIBAL-H) and solvent toluene. The reaction time is 1 hour with reaction temperature of -70 °C.
Uses of 2H-Pyran-2-ol,tetrahydro-: it can be used to produce 2-Phenylselanyl-tetrahydro-pyran at temperature of 25 °C. It will need reagent p-toluenesulfonic acid and solvent benzene. The yield is about 92%.
When you are using this chemical, please be cautious about it as the following:
It is harmful by inhalation and if swallowed. Besides, this chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing, gloves and eye/face protection. In case of 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: InChI=1/C5H10O2/c6-5-3-1-2-4-7-5/h5-6H,1-4H2
(2)InChIKey: CELWCAITJAEQNL-UHFFFAOYAE
(3)Std. InChI: InChI=1S/C5H10O2/c6-5-3-1-2-4-7-5/h5-6H,1-4H2
(4)Std. InChIKey: CELWCAITJAEQNL-UHFFFAOYSA-N
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