E-2,3-epoxy-1-octanyl tosylate
1-octen-3-ol
Conditions | Yield |
---|---|
With aluminum oxide; tellurium(2-) for 2.5h; | 100% |
With sodium hydroxide; tellurium; rongalite In tetrahydrofuran; water at 50℃; for 2h; | 80% |
With tellurium(2-) for 0.233333h; Product distribution; other reaction conditions, other reaction time, reagent, solvent; | |
Multi-step reaction with 2 steps 1: 97 percent / NaI / acetone / 3 h 2: 74 percent / Bu3SnAlEt2 / tetrahydrofuran / 1 h / 0 °C View Scheme |
3-(2-Methoxy-ethoxymethoxy)-oct-1-ene
1-octen-3-ol
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In tert-butyl alcohol for 3h; Heating; | 99% |
Conditions | Yield |
---|---|
With isocyanate de chlorosulfonyle; hydrogen; palladium diacetate; borohydride exchange resin In ethanol for 0.5h; | 97% |
With C16H26CuO In 2-methyl-propan-1-ol; toluene at 25℃; for 1h; | 92% |
With 2-methyl-propan-1-ol; [1,3-bis(2,6-di-iso-propylphenyl)imidazol-2-ylidene]copper(I) tert-butoxide In toluene at 25℃; for 1h; Inert atmosphere; Glovebox; chemoselective reaction; | 92% |
(E)-3-<(2-tetrahydropyranyl)oxy>-1-iodo-1-octene
1-octen-3-ol
Conditions | Yield |
---|---|
With trichloroisocyanuric acid In methanol at 20℃; for 5h; | 95% |
With water; lithium chloride In dimethyl sulfoxide at 90℃; for 6h; Hydrolysis; | 80% |
With magnesium bromide In diethyl ether for 2h; Ambient temperature; | 72% |
1-Octene, 3-(methoxymethoxy)-
1-octen-3-ol
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In tert-butyl alcohol for 3.5h; Heating; | 95% |
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol at 20℃; for 4h; | 93% |
With isoindoline; lithium aluminium tetrahydride In diethyl ether at -15℃; for 1.5h; |
N,N-Diethyl-O-(1-vinyl-hexyl)-hydroxylamine
1-octen-3-ol
Conditions | Yield |
---|---|
With zinc In acetic acid Ambient temperature; | 93% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 0℃; | 92% |
In tetrahydrofuran for 4h; Heating; | 75% |
In tetrahydrofuran at -15 - 20℃; | 74% |
Conditions | Yield |
---|---|
Stage #1: 1-Bromopentane With magnesium In tert-butyl methyl ether for 1h; Reflux; Stage #2: acrolein In tert-butyl methyl ether at -5 - 2℃; for 1h; | 92% |
Stage #1: 1-Bromopentane With iodine; magnesium In diethyl ether at 0℃; Inert atmosphere; Stage #2: acrolein In diethyl ether for 1.5h; Inert atmosphere; | 85% |
Stage #1: 1-Bromopentane With iodine; magnesium In diethyl ether Inert atmosphere; Stage #2: acrolein In diethyl ether at 0℃; | 85% |
3-Nitrooxy-oct-1-ene
1-octen-3-ol
Conditions | Yield |
---|---|
With acetic acid; zinc | 83% |
2,3-epoxyoctanol
1-octen-3-ol
Conditions | Yield |
---|---|
With diethyltitanium dichloride; zinc(II) chloride; zinc In tetrahydrofuran | 82% |
With diethyltitanium dichloride; zinc(II) chloride; zinc In tetrahydrofuran Product distribution; Mechanism; other 2,3-epoxy alcohols; | 82% |
Multi-step reaction with 3 steps 1: 91 percent / powdered KOH / diethyl ether / -10 deg C, then 0 deg C, 30 min 2: 97 percent / NaI / acetone / 3 h 3: 74 percent / Bu3SnAlEt2 / tetrahydrofuran / 1 h / 0 °C View Scheme |
E-2,3-epoxy-1-iodooctane
1-octen-3-ol
Conditions | Yield |
---|---|
With zinc In methanol for 3h; Heating; | 80% |
With Bu3SnAlEt2 In tetrahydrofuran at 0℃; for 1h; | 74% |
Conditions | Yield |
---|---|
In tetrahydrofuran; diethyl ether at -15℃; for 1.5h; Inert atmosphere; | 79% |
In tetrahydrofuran at 23℃; for 1h; Inert atmosphere; Cooling; | |
In tetrahydrofuran at 0 - 20℃; |
Conditions | Yield |
---|---|
Stage #1: Ethyl hexanoate With lithium diisobutyl-tert-butoxyaluminum hydride In tetrahydrofuran; hexane at 0℃; Stage #2: vinyl magnesium bromide In tetrahydrofuran; diethyl ether; hexane at 20℃; Stage #3: With hydrogenchloride; water In tetrahydrofuran; diethyl ether; hexane | 78% |
1-octen-3-ol
Conditions | Yield |
---|---|
With indium(III) chloride; sodium tetrahydroborate In acetonitrile at 20℃; for 7h; | 77% |
epoxybutene
n-butyllithium
A
1-octen-3-ol
B
2-butyl-but-3-en-1-ol
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate In diethyl ether at -105℃; for 0.5h; Ring cleavage; | A 16% B 75% |
1-octen-3-ol
Conditions | Yield |
---|---|
With 18-crown-6 ether In ethanol; water at 45℃; for 22h; Reagent/catalyst; Solvent; Temperature; Green chemistry; | 75% |
1-octen-3-ol
Conditions | Yield |
---|---|
With benzo[1,3,2]dioxaborole; Wilkinson's catalyst In tetrahydrofuran at 20℃; for 15h; | 65% |
2-octenol
1-octen-3-ol
Conditions | Yield |
---|---|
With silica-supported monomeric vanadium-oxo species In acetonitrile at 60℃; for 8h; Inert atmosphere; | 60% |
1-octen-3-ol
Conditions | Yield |
---|---|
With water; sodium hydrogencarbonate; bis-[(trifluoroacetoxy)iodo]benzene; meso-2,5-bis(methoxycarbonyl)-2,5-dimethylpyrrolidine-1-oxyl In dichloromethane at 20℃; for 2h; chemoselective reaction; | 55% |
oct-1-ene
A
octanol
B
1-octen-3-ol
C
2-octen-1-al
D
2-octenol
Conditions | Yield |
---|---|
With water; oxygen In ethanol at 75℃; for 24h; pH=3.7; | A n/a B 44% C 31% D n/a |
With water; oxygen In ethanol at 75℃; for 24h; pH=6.1; | A n/a B 32.5% C 14.9% D n/a |
Conditions | Yield |
---|---|
With potassium tert-butylate; tert-butyl alcohol for 336h; Ambient temperature; | A 40% B 10% |
ethanol
oct-1-ene
A
octanol
B
1-octen-3-ol
C
2-octen-1-al
D
n-octyl acetate
E
2-octenol
Conditions | Yield |
---|---|
With water; oxygen at 75℃; for 24h; pH=6.1; | A n/a B 31.7% C 20.8% D 6.8% E n/a |
oct-1-ene
acetonitrile
A
heptanal
B
octanol
C
1-octen-3-ol
D
2-octen-1-al
E
n-octyl acetate
F
1,2-Epoxyoctane
G
2-octenol
Conditions | Yield |
---|---|
With water; oxygen at 75℃; for 24h; | A 5.5% B n/a C 24.8% D 31.4% E 5.6% F 7.4% G n/a |
oct-1-ene
A
heptanal
B
octanol
C
1-octen-3-ol
D
2-octen-1-al
E
1,2-Epoxyoctane
F
2-octenol
Conditions | Yield |
---|---|
With water; oxygen In acetonitrile at 75℃; for 24h; | A 5.1% B n/a C 29.2% D 27.7% E 9.1% F n/a |
oct-1-ene
A
octanol
B
1-octen-3-ol
C
2-octen-1-al
D
1,2-Epoxyoctane
E
2-octenol
Conditions | Yield |
---|---|
With water; oxygen In acetonitrile at 75℃; for 24h; | A n/a B 26.2% C 26.2% D 6.9% E n/a |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); carbon dioxide; 2,5-di-tert-butyl-p-benzoquinone; water In 1,4-dioxane at 40℃; under 30003 Torr; for 72h; Inert atmosphere; Autoclave; | 18% |
Multi-step reaction with 2 steps 1.1: (MesPDI)CoMe / neat (no solvent) / 1 h / 23 °C 2.1: 3-chloro-benzenecarboperoxoic acid; disodium hydrogenphosphate / dichloromethane / 1 h / Cooling with ice 2.2: 16 h / 20 °C View Scheme |
Conditions | Yield |
---|---|
With meso-tetraphenylporphyrin iron(III) chloride; iodosylbenzene In dichloromethane for 0.5h; Ambient temperature; Yield given; | A 1% B n/a |
With dihydrogen peroxide In acetonitrile for 0.583333h; Ultrasonic irradiation; Reflux; | |
With dihydrogen peroxide In acetonitrile at 60℃; for 0.666667h; Ultrasonic irradiation; |
chloromethyl-(1-pentyl-allyl)-ether
A
formaldehyde-[bis-(1-pentyl-allyl)-acetal]
B
1-octen-3-ol
Conditions | Yield |
---|---|
With water | |
With sodium hydrogencarbonate |
oct-1-ene
A
oct-1-en-3-one
B
(E)-2-Octenal
C
(E)-oct-2-en-1-ol
D
1-octen-3-ol
E
1,2-Epoxyoctane
Conditions | Yield |
---|---|
With oxygen; bis(acetylacetonato)dioxidomolybdenum(VI); cobalt(III) acetylacetonate In 1,2-dichloro-benzene at 110℃; for 5.3h; Product distribution; other temperatures, catalysts, times, olefins; | A n/a B n/a C n/a D n/a E 61 % Chromat. |
Conditions | Yield |
---|---|
With cis-dichlorotetrakis(diemethylsulfoxide) ruthenium(II); sodium formate In water; toluene at 80℃; for 1h; Inert atmosphere; | 100% |
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; periodic acid In dichloromethane at 20℃; for 0.583333h; | 98% |
With chromium (VI) oxide In toluene for 0.333333h; microwave irradiation; | 98% |
Conditions | Yield |
---|---|
With glass encapsulated Rh-onium ion catalyst In toluene for 1.83333h; Heating; | 100% |
With potassium tert-butylate; trimethyl-4,6,9 hexaza-1,3,4,6,7,9 phospha-5 tricyclo<3.3.1.13,7>decane; dichloro(benzene)ruthenium(II) dimer In tetrahydrofuran at 75℃; for 0.25h; Kinetics; Product distribution; Further Variations:; Catalysts; Solvents; | 100% |
With C34H49ClFePRhS; hydrogen; sodium methylate In tetrahydrofuran at 82℃; under 22502.3 Torr; for 16h; Autoclave; Inert atmosphere; | 100% |
1-octen-3-ol
1,2-epoxy-3-octanol
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide In acetonitrile at 80℃; for 24h; Catalytic behavior; Reagent/catalyst; | 100% |
With tert.-butylhydroperoxide In chloroform for 4h; Catalytic behavior; Reflux; | 99% |
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 18h; | 95% |
Conditions | Yield |
---|---|
at 20℃; Inert atmosphere; neat (no solvent); | 100% |
Conditions | Yield |
---|---|
With propionic acid at 150℃; for 3h; Temperature; Claisen Rearrangement; | 99.9% |
Conditions | Yield |
---|---|
With propionic acid at 125℃; for 2h; Temperature; Claisen Rearrangement; | 99.5% |
With propionic acid at 105℃; for 4.5h; | 87% |
With propionic acid at 100 - 105℃; |
Conditions | Yield |
---|---|
With C12H8N2*2CH4O3S at 50℃; for 3h; | 99% |
With dmap In dichloromethane at 20℃; for 1.5h; | 94% |
aluminium dodecatungsten phosphate at 20℃; for 0.0833333h; | 93% |
Conditions | Yield |
---|---|
With Cp*2Sm(THF)2; cyclohexanone oxime acetate In toluene for 0.1h; Ambient temperature; | 99% |
With iron(III) trifluoromethanesulfonate at 20℃; for 5h; Schlenk technique; | 92% |
1-octen-3-ol
tris-(trimethylsilyl)silane
6-[tris(trimethylsilyl)]-3-octanol
Conditions | Yield |
---|---|
With 1,1'-azobis(1-cyanocyclohexanenitrile) In water at 100℃; for 4h; | 99% |
Conditions | Yield |
---|---|
With sodium tetrahydroborate; C11H18Cl2CoN2S; hydrogen In isopropyl alcohol at 100℃; under 37503.8 Torr; for 16h; Reagent/catalyst; Solvent; Glovebox; Autoclave; | 98% |
With hydrogen In ethanol at 20℃; under 760.051 Torr; for 1h; chemoselective reaction; | 94% |
Stage #1: 1-octen-3-ol With lithium triethylborohydride; cobalt(II) bromide In tetrahydrofuran Inert atmosphere; Glovebox; Stage #2: With hydrogen In tetrahydrofuran at 20℃; under 1500.15 Torr; for 3h; | 93% |
1-octen-3-ol
propionic acid
Triethyl orthoacetate
ethyl trans-4-decenoate
Conditions | Yield |
---|---|
120 deg C, then 160 deg C, 2 h; | 98% |
Conditions | Yield |
---|---|
With n-butyllithium; tert-butylmagnesium chloride In diethyl ether; hexane | 98% |
Stage #1: 1-octen-3-ol With n-butyllithium In tetrahydrofuran; hexane Inert atmosphere; Stage #2: 1,2-dibromomethane With tert-butylmagnesium chloride In tetrahydrofuran; hexane Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
With 2.9-dimethyl-1,10-phenanthroline; palladium diacetate; silver carbonate In acetonitrile at 60℃; for 24h; regioselective reaction; | 98% |
With 2.9-dimethyl-1,10-phenanthroline; palladium diacetate; copper(l) chloride In dimethyl sulfoxide at 50℃; under 760.051 Torr; for 12h; | 98% |
With oxygen; palladium diacetate; acetic acid; copper(l) chloride In dimethyl sulfoxide at 50℃; under 760.051 Torr; for 20h; regioselective reaction; | 94% |
Conditions | Yield |
---|---|
Stage #1: 1-octen-3-ol With [Ir(III)(η5-pentamethylcyclopentadienyl)(H2O)3](SO4); iodine; oxygen; sodium nitrite In 2-methyltetrahydrofuran; water under 760.051 Torr; for 24h; Sealed tube; Stage #2: Thiomorpholin In 2-methyltetrahydrofuran; water for 16h; | 98% |
1-octen-3-ol
tert-butyldimethylsilyl chloride
tert-butyl-dimethyl-(1-vinyl-hexyloxy)-silane
Conditions | Yield |
---|---|
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 68h; | 97% |
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 25℃; for 0.5h; | 95% |
With zinc In benzene at 20℃; for 1h; | 53% |
With pyridine In dichloromethane at 0 - 20℃; |
1-octen-3-ol
1-iodohept-2-ene
Conditions | Yield |
---|---|
With zirconium(IV) chloride; sodium iodide In acetonitrile for 0.0833333h; Heating; | 95% |
dichloroacethyl chloride
1-octen-3-ol
1-pentyl-2-propenyl dichloroacetate
Conditions | Yield |
---|---|
With dmap In dichloromethane at 20℃; for 2h; | 95% |
Conditions | Yield |
---|---|
With dmap In dichloromethane | 95% |
Stage #1: 1-octen-3-ol With pyridine In dichloromethane at 0℃; Inert atmosphere; Stage #2: acetyl chloride In dichloromethane at 0 - 20℃; Inert atmosphere; |
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine In dichloromethane for 12h; Inert atmosphere; Reflux; | 95% |
With N-ethyl-N,N-diisopropylamine In dichloromethane for 12h; Inert atmosphere; Reflux; | 95% |
Conditions | Yield |
---|---|
With 2.9-dimethyl-1,10-phenanthroline; palladium diacetate; copper(l) chloride In dimethyl sulfoxide at 50℃; under 760.051 Torr; for 12h; | 95% |
Conditions | Yield |
---|---|
With [O,O’-((S)-1,1´-dinaphthyl-2,2´-diyl)-N,N´-di-(S,S)-1-(2-methoxyphenyl)ethylphosphoramidite]; (S)-1,1'-binaphthyl-2,2'-diyl hydrogen phosphate; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 25℃; for 12h; Inert atmosphere; Schlenk technique; enantioselective reaction; | 95% |
Conditions | Yield |
---|---|
94% |
Conditions | Yield |
---|---|
With magnesium bromide; (dppe)NiHCl In tetrahydrofuran at -50 - 20℃; for 1h; | 94% |
Conditions | Yield |
---|---|
Stage #1: 1-octen-3-ol With oxygen; palladium diacetate In N,N-dimethyl-formamide at 90℃; under 760.051 Torr; for 4h; Green chemistry; Stage #2: phenylboronic acid With 2.9-dimethyl-1,10-phenanthroline In N,N-dimethyl-formamide at 90℃; for 18h; Heck Reaction; Green chemistry; | 94% |
Molecular Structure of 1-Octen-3-ol (CAS NO.3391-86-4):
IUPAC Name: Oct-1-en-3-ol
Canonical SMILES: CCCCCC(C=C)O
InChI: InChI=1S/C8H16O/c1-3-5-6-7-8(9)4-2/h4,8-9H,2-3,5-7H2,1H3
InChIKey: VSMOENVRRABVKN-UHFFFAOYSA-N
Molecular Weight: 128.21204 [g/mol]
Molecular Formula: C8H16O
XLogP3-AA: 2.6
H-Bond Donor: 1
H-Bond Acceptor: 1
EINECS: 222-226-0
Index of Refraction: 1.438
Molar Refractivity: 40.33 cm3
Molar Volume: 153.5 cm3
Surface Tension: 28 dyne/cm
Density: 0.834 g/cm3
Flash Point: 61.1 °C
Enthalpy of Vaporization: 47.13 kJ/mol
Boiling Point: 168.4 °C at 760 mmHg
Vapour Pressure: 0.531 mmHg at 25 °C
Appearance: Clear colorless to pale yellow liquid
Melting Point: -49 °C
Product Categories: API intermediates; alcohol Flavor
1-Octen-3-ol (CAS NO.3391-86-4) is used in combination with carbon dioxide to attract insects in order to kill them with certain electronic devices. Its odor has been described as green and moldy or meaty; it is used in certain perfumes.
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | intravenous | 56mg/kg (56mg/kg) | U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#02545, | |
rabbit | LD50 | skin | 3300mg/kg (3300mg/kg) | Food and Cosmetics Toxicology. Vol. 14, Pg. 681, 1976. | |
rat | LD50 | oral | 340mg/kg (340mg/kg) | Food and Cosmetics Toxicology. Vol. 14, Pg. 681, 1976. |
Reported in EPA TSCA Inventory.
Safety Information of 1-Octen-3-ol (CAS NO.3391-86-4):
Hazard Codes: Xn
Risk Statements: 22-36/38-20/21/22
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
R22:Harmful if swallowed.
R36/38:Irritating to eyes and skin.
Safety Statements: 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
RIDADR: 2810
WGK Germany: 3
RTECS: RH3300000
HazardClass: 6.1(b)
PackingGroup: III
Poison by ingestion and intravenous routes. Moderately toxic by skin contact. When heated to decomposition it emits acrid smoke and irritating fumes.
1-Octen-3-ol (CAS NO.3391-86-4), its Synonyms are 1-Okten-3-ol ; 1-Vinylhexanol ; 3-Hydroxy-1-octene ; 3-Octenol ; Amyl vinyl carbinol ; Amylvinylcarbinol ; Matsuica alcohol ; Matsutake alcohol ; Pentyl vinyl carbinol ; Pentylvinylcarbinol ; Vinyl amyl carbinol .
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