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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% |
rac-3-octanol
Conditions | Yield |
---|---|
With dimethylbromosulphonium bromide In methanol; dichloromethane at 20℃; for 0.416667h; | 92% |
With zinc tetrafluoroborate In methanol; dichloromethane; water at 20℃; for 0.416667h; | 92% |
3-(t-butyldimethylsiloxy)octane
rac-3-octanol
Conditions | Yield |
---|---|
With acetonyltriphenylphosphonium bromide In methanol; dichloromethane at 20℃; for 0.366667h; | 91% |
With titanium tetrachloride; ethyl acetate In chlorobenzene at -18℃; for 0.5h; |
Conditions | Yield |
---|---|
With isopropyl alcohol at 80℃; for 24h; Inert atmosphere; | 85% |
With C29H34BNOP2Ru In ethanol; dichloromethane Schlenk technique; Inert atmosphere; Reflux; | 80% |
With ammonium hydroxide; sodium tetrahydroborate In ethanol; water for 3h; Ambient temperature; | 79.02% |
(S)-octan-3-ol
rac-3-octanol
Conditions | Yield |
---|---|
With (η(5)-C5Me5)RuCl(1,3-bis(cyclohexyl)imidazol-2-ylidene); sodium t-butanolate In toluene at 20℃; | 84% |
With C32H42N2ORu In toluene at 50℃; | 82% |
Conditions | Yield |
---|---|
With sodium carbonate decahydrate; dichlororuthenium(II) (p-cymene)(1,3,5-triaza-7-phosphaadamantane); hydrogen In water at 75℃; under 750.075 Torr; pH=7; Catalytic behavior; Schlenk technique; | A 81% B 17% |
With Fe(bis[(diisopropylphosphino)ethyl]amine)(CO)(H)(BH4); potassium tert-butylate; isopropyl alcohol at 80℃; for 1h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; | A 28% B 60% |
With isopropyl alcohol under 760.051 Torr; for 2h; Inert atmosphere; Heating; | A 6 %Chromat. B 94 %Chromat. |
Conditions | Yield |
---|---|
In diethyl ether at 0 - 20℃; | 53% |
Conditions | Yield |
---|---|
With ethanol at 90℃; under 10343.2 Torr; for 16h; Catalytic behavior; Inert atmosphere; | 44% |
With carbon-supported single-site molybdenum dioxo In ethanol at 90℃; under 10343.2 Torr; for 16h; Time; Inert atmosphere; | 44 %Spectr. |
octane
A
3-octanone
B
octan-4-one
C
octan-4-ol
D
rac-3-octanol
E
rac-octan-2-ol
F
hexyl-methyl-ketone
Conditions | Yield |
---|---|
With [PPh4]2[MnV(N)(CN)4]; tetrabutylammonium periodite; acetic acid In 2,2,2-trifluoroethanol at 23℃; Inert atmosphere; | A 14% B 14% C 18% D 18% E 20% F 16% |
With [PPh4]2[MnV(N)(CN)4]; dihydrogen peroxide; acetic acid In 2,2,2-trifluoroethanol at 23℃; for 5h; Inert atmosphere; | A 14% B 14% C 18% D 19% E 17% F 15% |
With Co(III)(BPI)(OAc)(OO-tBu) at 60℃; for 2h; Product distribution; stoichiometric oxidation by various cobalt(III)alkylperoxy complexes; further products; | A 7.8% B 8.3% C 4.6% D 5% E 7% F 12% |
Conditions | Yield |
---|---|
With diethyl ether |
Conditions | Yield |
---|---|
With diethyl ether |
Conditions | Yield |
---|---|
ueber (+-)-3-Acetoxy-octan; |
Conditions | Yield |
---|---|
With chloro-trimethyl-silane; zinc In dichloromethane for 0.0833333h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
octane
A
octanol
B
octan-4-ol
C
rac-3-octanol
D
rac-octan-2-ol
Conditions | Yield |
---|---|
With iodosylbenzene; MnTTPPP(OAc) In benzene at 25℃; for 7h; Mechanism; other catalysts and regioselectivity investigated; | |
With potassium hydroxide; dihydrogen peroxide 1.) ethyl acetate, 5 h, irradiation; 2.) methanol, 4 h, reflux; Yield given. Multistep reaction. Yields of byproduct given; | |
With dihydrogen peroxide; chromic acid In acetonitrile at 60℃; under 750.06 Torr; for 1h; Product distribution; |
Conditions | Yield |
---|---|
With isozyme P-450b for 0.166667h; Product distribution; Mechanism; P-450 reductase, NADPH, phosphatidylcholine (pH 8.2); var. isozymes of cytochrome P-450; | |
With cytochrome P450 BM3 from Bacillus megaterium 77-9H mutation; oxygen; NADPH In phosphate buffer; ethanol at 25℃; under 1050.08 Torr; for 12h; pH=8.0; Title compound not separated from byproducts; | |
With cytochrome P450 BM-3 enzyme mutant 12-10C; nicotinamide adenine dinucleotide phosphate In aq. phosphate buffer; ethanol pH=8.0; Catalytic behavior; Kinetics; Reagent/catalyst; Enzymatic reaction; | |
With cytochrome P450 BM-3 enzyme mutant 29-3E; nicotinamide adenine dinucleotide phosphate In aq. phosphate buffer; ethanol pH=8.0; Catalytic behavior; Kinetics; Reagent/catalyst; Enzymatic reaction; regiospecific reaction; |
octane
A
3-octanone
B
octan-4-one
C
octan-4-ol
D
rac-3-octanol
Conditions | Yield |
---|---|
With (pyridine-2-carboxylate)VO(O2)(H2O)2 In acetonitrile at 20℃; for 5h; Further byproducts given; | A 2.9 % Chromat. B 2.8 % Chromat. C 0.5 % Chromat. D 0.5 % Chromat. |
octane
A
3-octanone
B
octan-4-one
C
rac-3-octanol
D
hexyl-methyl-ketone
Conditions | Yield |
---|---|
With (pyridine-2-carboxylate)VO(O2)(H2O)2 In acetonitrile at 20℃; for 5h; Further byproducts given; | A 2.9 % Chromat. B 2.8 % Chromat. C 0.5 % Chromat. D 2.4 % Chromat. |
octane
A
3-octanone
B
octan-4-ol
C
rac-3-octanol
D
hexyl-methyl-ketone
Conditions | Yield |
---|---|
With (pyridine-2-carboxylate)VO(O2)(H2O)2 In acetonitrile at 20℃; for 5h; Further byproducts given; | A 2.9 % Chromat. B 0.5 % Chromat. C 0.5 % Chromat. D 2.4 % Chromat. |
With Titanium substituted ZSM-5; dihydrogen peroxide In butanone at 80℃; for 4h; Yield given. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts; |
octane
A
octan-4-one
B
octan-4-ol
C
rac-3-octanol
D
hexyl-methyl-ketone
Conditions | Yield |
---|---|
With (pyridine-2-carboxylate)VO(O2)(H2O)2 In acetonitrile at 20℃; for 5h; Further byproducts given; | A 2.8 % Chromat. B 0.5 % Chromat. C 0.5 % Chromat. D 2.4 % Chromat. |
octane
A
octan-4-ol
B
rac-3-octanol
C
rac-octan-2-ol
D
hexyl-methyl-ketone
Conditions | Yield |
---|---|
With (pyridine-2-carboxylate)VO(O2)(H2O)2 In acetonitrile at 20℃; for 5h; Further byproducts given; | A 0.5 % Chromat. B 0.5 % Chromat. C 1.5 % Chromat. D 2.4 % Chromat. |
With Titanium substituted ZSM-5; dihydrogen peroxide In butanone at 80℃; for 4h; Yield given. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts; | |
With bis(acetylacetonate)oxovanadium; dihydrogen peroxide In acetic acid at 30℃; Product distribution; | |
With oxygen; NADPH; CYP monooxygenase CYP102A1 mutant A74G In phosphate buffer; dimethyl sulfoxide at 20℃; for 100h; pH=6; Further byproducts given. Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
With sodium persulfate; silver nitrate In water; acetonitrile Heating; |
Conditions | Yield |
---|---|
With sodium hydrogensulfide; lithium nitrate 1.) MeCN/Et2O/H2O, 10 deg C, anodic oxidation condition; 2.) EtOH; Yield given. Yields of byproduct given. Title compound not separated from byproducts; | |
Stage #1: trans-2-Octene With 2-(perfluorooctyl)ethyl methyl sulfide*BH3 In dichloromethane at 0℃; for 1h; Stage #2: With sodium hydroxide; dihydrogen peroxide In dichloromethane; water Further stages.; | |
With C11H7F17S(1+)B(1-)H3; 3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluorodecyl methyl sulfide In FC-72; dichloromethane |
Conditions | Yield |
---|---|
Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With sodium hydroxide; dihydrogen peroxide 1.) THF, hexane, 0 deg C, 0.5 h, 2.) THF, hexane, methanol, 68 deg C, 72 h; Yield given. Multistep reaction; |
Butane-1,4-diol
butan-1-ol
A
3-hydroxymethyl-1,7-heptanediol
B
rac-3-octanol
C
2-(n-butyl)-1,4-butanediol
D
2-(1-hydroxymethylpropyl)tetrahydrofuran
Conditions | Yield |
---|---|
With chromium(III) oxide; sodium; nickel 2) reflux, 20 h, separation of water; Yield given. Multistep reaction. Further byproducts given; |
Butane-1,4-diol
butan-1-ol
A
rac-3-octanol
B
2-(n-butyl)-1,4-butanediol
C
2-(1-hydroxymethylpropyl)tetrahydrofuran
D
2-(1-hydroxymethyl-3-hydroxypropyl)tetrahydrofuran
Conditions | Yield |
---|---|
With chromium(III) oxide; sodium; nickel 2) reflux, 20 h, separation of water; Yield given. Multistep reaction. Further byproducts given; |
octane
A
3-octanone
B
octan-4-one
C
rac-3-octanol
D
rac-octan-2-ol
Conditions | Yield |
---|---|
With Titanium substituted ZSM-5; dihydrogen peroxide In butanone at 80℃; for 4h; Yield given. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts; |
octane
A
octan-4-one
B
octan-4-ol
C
rac-3-octanol
D
rac-octan-2-ol
Conditions | Yield |
---|---|
With Titanium substituted ZSM-5; dihydrogen peroxide In butanone at 80℃; for 4h; Yield given. Further byproducts given. Yields of byproduct given. Title compound not separated from byproducts; | |
With purified cytochrome P450 BM-3 (Bacillus megaterium); tris hydrochloride; NADPH In water; dimethyl sulfoxide at 20℃; for 2h; Enzyme kinetics; Product distribution; Further Variations:; Reagents; Enzymatic reaction; |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; lithium aluminium tetrahydride; 4 A molecular sieve; manganese(IV) oxide 1) benzene, 60 deg C, 48 h, 2) Et2O, r.t.; Yield given. Multistep reaction. Yields of byproduct given; | |
With L188Q mutant; sol-gel immobilised P450 BM-3 A74G; NADPH In phosphate buffer; dimethyl sulfoxide for 2h; pH=7.5; Enzymatic reaction; | |
With NADPH In dimethyl sulfoxide at 30℃; pH=7.4; Product distribution; Further Variations:; Reagents; | A 42 % Chromat. B 43 % Chromat. C 15 % Chromat. |
Conditions | Yield |
---|---|
With tetrabutoxytitanium at 170 - 220℃; for 4.5h; Inert atmosphere; Large scale; | 99% |
Conditions | Yield |
---|---|
With 1-methyl-1H-imidazole; triethylamine In toluene at 20 - 25℃; for 1h; Inert atmosphere; | 98% |
With trimethylamine hydrochloride; triethylamine In toluene at 0 - 5℃; for 1h; | 94% |
With N,N,N',N'-tetramethylhexamethylenediamine In toluene at 0 - 5℃; for 1h; mesylation; | 94% |
With triethylamine In dichloromethane at 20℃; Sealed tube; |
Conditions | Yield |
---|---|
With 1-methyl-1H-imidazole; N,N,N,N,-tetramethylethylenediamine In acetonitrile at 0 - 25℃; for 2h; | 98% |
rac-3-octanol
Conditions | Yield |
---|---|
With urea In 1,3,5-trimethyl-benzene at 141℃; under 760.051 Torr; for 20h; Inert atmosphere; | 98% |
Conditions | Yield |
---|---|
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite pentahydrate; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane at 5℃; for 1h; Temperature; | 97% |
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hypochlorite pentahydrate; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane at 5℃; for 0.5h; | 96% |
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; periodic acid In dichloromethane at 20℃; for 0.75h; | 95% |
Conditions | Yield |
---|---|
With 1-methyl-1H-imidazole; N,N,N,N,-tetramethylethylenediamine In acetonitrile at 0 - 25℃; for 2h; | 97% |
rac-3-octanol
p-toluenesulfonyl chloride
octan-3-yl 4-methylbenzenesulfonate
Conditions | Yield |
---|---|
With N,N,N',N'-tetramethylhexamethylenediamine; triethylamine In acetonitrile at 0 - 20℃; for 4h; Tosylation; | 95% |
With 1-methyl-1H-imidazole; triethylamine In toluene at 20 - 25℃; for 1h; Inert atmosphere; | 94% |
With trimethylamine hydrochloride; triethylamine In dichloromethane at 0 - 5℃; for 1h; | 93% |
Conditions | Yield |
---|---|
In 5,5-dimethyl-1,3-cyclohexadiene at 130℃; for 12h; Inert atmosphere; | 94.7% |
With [RuCl(p-cymene)(1,3-dibenzylbenzimidazolin-2-ylidene)(PPh3)]PF6 In neat (no solvent) at 130℃; for 18h; Reagent/catalyst; | 49% |
Conditions | Yield |
---|---|
With dihydrogen peroxide; methyltrioxorhenium(VII); sodium bromide In acetic acid for 10h; Ambient temperature; | A 94% B 6% |
Conditions | Yield |
---|---|
With 1-methyl-1H-imidazole; N,N,N,N,-tetramethylethylenediamine; potassium carbonate In potassium hydroxide at 20 - 25℃; for 2h; pH=11.5; Schotten-Baumann-type reaction; | 94% |
With 1-methyl-1H-imidazole; N,N,N,N,-tetramethylethylenediamine In acetonitrile at 0 - 25℃; for 2h; | 94% |
rac-3-octanol
(S)-(-)-3,3,3-Trifluormilchsaeure
Conditions | Yield |
---|---|
In benzene Esterification; Heating; | 92% |
Conditions | Yield |
---|---|
bismuth(III) nitrate In dichloromethane at 20℃; for 0.3h; | 90% |
With dimethylbromosulphonium bromide at 20℃; for 0.0833333h; | 87% |
With zinc tetrafluoroborate In dichloromethane; water at 20℃; for 0.166667h; | 87% |
Conditions | Yield |
---|---|
With sulfuric acid; 2,6-di-tert-butyl-4-hydroxytoluene In benzene at 90℃; for 2.5h; Heating / reflux; | 90% |
Conditions | Yield |
---|---|
With 1-methyl-1H-imidazole; N,N,N,N,-tetramethylethylenediamine; potassium carbonate In potassium hydroxide at 20 - 25℃; for 2h; pH=11.5; Schotten-Baumann-type reaction; | 89% |
Conditions | Yield |
---|---|
With 1-methyl-1H-imidazole; N,N,N,N,-tetramethylethylenediamine In acetonitrile at 0 - 25℃; for 2h; | 89% |
With 1-methyl-1H-imidazole; N,N,N,N,-tetramethylethylenediamine; potassium carbonate In potassium hydroxide at 20 - 25℃; for 1.5h; pH=11.5; Schotten-Baumann-type reaction; | 72% |
rac-3-octanol
Conditions | Yield |
---|---|
Stage #1: rac-3-octanol With sodium hydride In 1,4-dioxane at 20℃; for 1h; Stage #2: With triethylamine sulfurtrioxide In 1,4-dioxane at 20℃; | 87% |
rac-3-octanol
2,2,6-trimethyl-4H-1,3-dioxin-4-one
Methyl-2-n-Heptyl Acetoacetate
Conditions | Yield |
---|---|
In xylene at 150℃; for 0.5h; | 86% |
Conditions | Yield |
---|---|
With 1-methyl-1H-imidazole; N,N,N,N,-tetramethylethylenediamine In acetonitrile at 0 - 5℃; for 1h; | 86% |
With 1-methyl-1H-imidazole; N,N,N,N,-tetramethylethylenediamine; potassium carbonate In potassium hydroxide at 20 - 25℃; for 1.5h; pH=11.5; Schotten-Baumann-type reaction; | 85% |
rac-3-octanol
tetradecane-1,2-diol
A
3-octanone
B
1-tetradecene
Conditions | Yield |
---|---|
With methyltrioxorhenium(VII) In dodecane at 80 - 175℃; Catalytic behavior; Kinetics; Temperature; | A n/a B 85% |
rac-3-octanol
Conditions | Yield |
---|---|
With sulfuric acid at 100℃; for 3h; Inert atmosphere; | 84% |
rac-3-octanol
rac-3-octyl sulfate
Conditions | Yield |
---|---|
With triethylamine sulfur trioxide | 83% |
With triethylamine sulfur trioxide |
Conditions | Yield |
---|---|
Mitsunobu Displacement; Sonication; | 83% |
Conditions | Yield |
---|---|
With Knoelker’s complex; silver fluoride In toluene at 110℃; for 48h; Inert atmosphere; Sealed tube; | 82% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0℃; | 81% |
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