(R)-2-octyl sulfate
(S)-2-Octanol
Conditions | Yield |
---|---|
With His-tagged Pseudomonas sp. metallo-β-lactamase-type alkylsulfatase Pisa1; water; tris hydrochloride at 30℃; for 6h; pH=8.2; Enzymatic reaction; optical yield given as %ee; stereoselective reaction; | 100% |
Conditions | Yield |
---|---|
With alcohol dehydrogenase from Lactobacillus kefir; alcohol dehydrogenase from Rhodococcus ruber DSM 44541; YcnD-oxidoreductase at 30℃; for 3h; pH=7.5; aq. buffer; Resolution of racemate; Enzymatic reaction; optical yield given as %ee; enantiospecific reaction; | 99% |
With phosphate buffer; tributyrin for 140h; Ambient temperature; | 77% |
Conditions | Yield |
---|---|
With NAD; Co2+immobilized acetophenone reductase from Geotrichum candidum In aq. phosphate buffer; isopropyl alcohol at 30℃; for 3h; pH=7.2; Green chemistry; Enzymatic reaction; enantioselective reaction; | 99% |
With glucose dehydrogenase; D-Glucose; alcohol dehydrogenase from Thermoanaerobacter sp.; NADPH In aq. buffer at 30℃; for 24h; pH=7.5; Concentration; Time; Ionic liquid; Green chemistry; Enzymatic reaction; enantioselective reaction; | 85% |
With acetophenone reductase from Geotrichum candidum NBRC 4597; NAD In isopropyl alcohol at 30℃; for 3h; pH=7.2; Enzymatic reaction; enantioselective reaction; | 85% |
(R)-2-octyl sulfate
(S)-2-Octanol
Conditions | Yield |
---|---|
With His-tagged Pseudomonas sp. metallo-β-lactamase-type alkylsulfatase Pisa1; water; tris hydrochloride at 30℃; for 6h; pH=8.2; Enzymatic reaction; optical yield given as %ee; stereoselective reaction; | 100% |
Conditions | Yield |
---|---|
With alcohol dehydrogenase from Lactobacillus kefir; alcohol dehydrogenase from Rhodococcus ruber DSM 44541; YcnD-oxidoreductase at 30℃; for 3h; pH=7.5; aq. buffer; Resolution of racemate; Enzymatic reaction; optical yield given as %ee; enantiospecific reaction; | 99% |
With phosphate buffer; tributyrin for 140h; Ambient temperature; | 77% |
Conditions | Yield |
---|---|
With NAD; Co2+immobilized acetophenone reductase from Geotrichum candidum In aq. phosphate buffer; isopropyl alcohol at 30℃; for 3h; pH=7.2; Green chemistry; Enzymatic reaction; enantioselective reaction; | 99% |
With glucose dehydrogenase; D-Glucose; alcohol dehydrogenase from Thermoanaerobacter sp.; NADPH In aq. buffer at 30℃; for 24h; pH=7.5; Concentration; Time; Ionic liquid; Green chemistry; Enzymatic reaction; enantioselective reaction; | 85% |
With acetophenone reductase from Geotrichum candidum NBRC 4597; NAD In isopropyl alcohol at 30℃; for 3h; pH=7.2; Enzymatic reaction; enantioselective reaction; | 85% |
rac-octan-2-ol
A
(S)-2-Octanol
B
(R)-Octan-2-ol
C
hexyl-methyl-ketone
Conditions | Yield |
---|---|
With Arthrobacter atrocyaneus In N,N-dimethyl-formamide at 32℃; for 48h; Microbiological reaction; enantioselective reaction; | A 94% B n/a C n/a |
With lyophilised cells of Escherichia coli overexpressing the solvent-tolerant alcohol dehydrogenase from Rhodococcus ruber DSM44541 In aq. buffer at 30℃; for 24h; pH=7.5; Reagent/catalyst; Resolution of racemate; Enzymatic reaction; | A n/a B n/a C n/a |
With NADP In acetone at 50℃; for 22h; pH=8; Resolution of racemate; |
(R)-(+)-2-hydroxyoctyl tosylate
(S)-2-Octanol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In tetrahydrofuran | 93% |
Conditions | Yield |
---|---|
With water; sodium hydroxide In methanol for 6h; Reflux; Inert atmosphere; | 87% |
With potassium hydroxide Heating; | 3.4 g |
rac-2-octyl sulfate
(S)-2-Octanol
Conditions | Yield |
---|---|
Stage #1: rac-2-octyl sulfate With His-tagged Pseudomonas sp. metallo-β-lactamase-type alkylsulfatase Pisa1; water; tris hydrochloride at 30℃; for 24h; pH=8.2; Resolution of racemate; Enzymatic reaction; Stage #2: With water; toluene-4-sulfonic acid In 1,4-dioxane; tert-butyl methyl ether at 40℃; for 5h; optical yield given as %ee; stereoselective reaction; | 87% |
Multi-step reaction with 2 steps 1: His-tagged Pseudomonas sp. metallo-β-lactamase-type alkylsulfatase Pisa1; water; tris hydrochloride / 6 h / 30 °C / pH 8.2 / Resolution of racemate; Enzymatic reaction 2: water; toluene-4-sulfonic acid / 1,4-dioxane; tert-butyl methyl ether / 2 h / 40 °C View Scheme |
(S)-2-Octanol
Conditions | Yield |
---|---|
With sodium hypophosphite; Raney-Ni (W-2) In ethanol; water for 0.5h; Ambient temperature; pH=5.2; | 85% |
With sodium hypophosphite; Raney Ni(W-2) In ethanol; water for 0.5h; Ambient temperature; | 75% |
(S)-N-(oct-2-yloxy)-4-(p-chlorophenyl)-thiazole-2(3H)-thione
(S)-2-Octanol
Conditions | Yield |
---|---|
With tri-n-butyl-tin hydride In dichloromethane at 18℃; for 0.416667h; Inert atmosphere; Photolysis; enantioselective reaction; | 85% |
(R)-1-Phenylsulfanyl-octan-2-ol
(S)-2-Octanol
Conditions | Yield |
---|---|
With sodium hypophosphite; Raney Ni(W-2) In ethanol; water for 0.5h; Ambient temperature; | 84% |
With sodium hypophosphite; Raney-Ni (W-2) In ethanol; water for 0.5h; Ambient temperature; pH=5.2; | 84% |
(S)-2-Octanol
Conditions | Yield |
---|---|
With sodium hypophosphite; Raney Ni(W-2) In ethanol; water for 0.5h; Ambient temperature; | 82% |
With sodium hypophosphite; Raney-Ni (W-2) In ethanol; water for 0.5h; Ambient temperature; pH=5.2; | 82% |
Conditions | Yield |
---|---|
A 77% B 75% |
Conditions | Yield |
---|---|
(1S,2R)-(-)-2-(N,N-di-n-butylamino)-1-phenylpropan-1-ol In hexane 1.) r.t., 20 min; 2.) 0 deg C, 16 h; | 70% |
Conditions | Yield |
---|---|
With methanesulfonic acid; (R,R)-dihydroborate In hexane at -20℃; for 48h; Title compound not separated from byproducts; | A n/a B 68% |
With hydrogen; tartaric acid-NaBr-mod. Raney nickel In tetrahydrofuran at 100℃; for 8h; Product distribution; enantioface hydrogenation with various carboxylic acids; | |
With hydrogen; TA-NaBr-MRNi In tetrahydrofuran at 60℃; under 66195.7 Torr; for 96h; Product distribution; RNi(prepared from 3.8 g of the alloy(Ni/Al=42/58))modified with 200 ml of aq. solution containing (R,R)-TA(2 g) and NaBr(12 g) at pH 3.2, 100 deg C for 1 h. hydrogenations of var. 2-alkanones, reactions at var. temperatures; |
rac-octan-2-ol
benzeneacetic acid methyl ester
A
(S)-2-Octanol
B
(R)-Octan-2-ol
C
(R)-2-octyl phenylacetate
D
hexyl-methyl-ketone
Conditions | Yield |
---|---|
With [(C4Ph4COHOCC4Ph4)(μ-H)][(CO)4Ru2]; Novozym(R) 435; 2,4-dimethylpentan-3-one In toluene at 70℃; under 142.511 Torr; for 40h; | A n/a B n/a C 63% D n/a |
(S)-N-(oct-2-yloxy)-pyridine-2(1H)-thione
(S)-2-Octanol
Conditions | Yield |
---|---|
With tri-n-butyl-tin hydride In dichloromethane at 18℃; for 0.0333333h; Inert atmosphere; Photolysis; enantioselective reaction; | 59% |
Conditions | Yield |
---|---|
With Candida antarctica lipase B; 1-(10-carboxydecyl)-3-methylimidazolium hexafluorophosphate; diisopropyl-carbodiimide In acetone at 40℃; for 2h; Resolution of racemate; Enzymatic reaction; enantioselective reaction; | A 51% B 35% |
Title compound not separated from byproducts; | |
With sodium acetate In water at 40℃; enantioselective reaction; | A n/a B n/a |
Conditions | Yield |
---|---|
With Candida antarctica lipase B In acetone at 35℃; for 3h; Resolution of racemate; Enzymatic reaction; enantioselective reaction; | A 51% B n/a |
vinyl acetate
rac-octan-2-ol
A
(S)-2-Octanol
B
(R)-2-octyl acetate
Conditions | Yield |
---|---|
With sol-gel encapsulated Candida antarctica lipase SP 525 at 20℃; for 17h; | A 50% B 47% |
With 4 A molecular sieve; immobilized lipase PS In di-isopropyl ether at 30℃; for 15h; | A 49% B 48.7% |
With immobilized lipase B from Candida antarctica In hexane at 32℃; for 1h; Resolution of racemate; Enzymatic reaction; | A 40% B 35% |
(S)-N-(oct-2-yloxy)-4-methylthiazole-2(3H)-thione
(S)-2-Octanol
Conditions | Yield |
---|---|
With tri-n-butyl-tin hydride In dichloromethane at 18℃; for 0.416667h; Inert atmosphere; Photolysis; enantioselective reaction; | 50% |
(R)-octan-2-yl methanesulfonate
(S)-2-Octanol
Conditions | Yield |
---|---|
With sulfuric acid In tetrahydrofuran for 19h; Heating; | 46% |
Conditions | Yield |
---|---|
With Lipase Amano AK at 20℃; for 72h; pH=7; aq. phosphate buffer; Enzymatic reaction; | A 42% B 43% |
Conditions | Yield |
---|---|
With oleic acid hydratase from Elizabethkingia meningoseptica A248L mutant; water; hexanoic acid In dimethyl sulfoxide at 25℃; for 144h; pH=6; Reagent/catalyst; Enzymatic reaction; enantioselective reaction; | 22% |
(S)-2-Octanol
Conditions | Yield |
---|---|
bei der Verseifung; succinic acid methyl ester--ester; |
(S)-2-Octanol
Conditions | Yield |
---|---|
Hydrolysis; malonic acid ethyl ester--ester; |
(S)-2-Octanol
Conditions | Yield |
---|---|
bei der Verseifung; succinic acid ethyl ester--ester; |
malonic acid bis-(1-methyl-heptyl ester)
(S)-2-Octanol
Conditions | Yield |
---|---|
Hydrolysis; malonic acid di--ester; |
bis(1-methylheptyl)butanedioate
(S)-2-Octanol
Conditions | Yield |
---|---|
bei der Verseifung; succinic acid di--ester; |
(S)-2-Octanol
(S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride
(R)-2-octyl (R)-α-methoxy-α-trifluoromethylphenylacetate
Conditions | Yield |
---|---|
With dmap In dichloromethane at 0 - 20℃; | 100% |
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 20℃; for 13h; | 99% |
With pyridine | 93.1% |
for 1h; Heating; | 82% |
With dmap at 30℃; for 18h; | |
With dmap |
(S)-2-Octanol
(R)-(-)-2-iodooctane
Conditions | Yield |
---|---|
With 1H-imidazole; iodine; triphenylphosphine In dichloromethane for 1h; Ambient temperature; | 98% |
With iodine In Petroleum ether for 6h; Heating; | 25% |
With hydrogen iodide |
(S)-2-Octanol
methanesulfonyl chloride
(S)-2-<(Methanesulfonyl)oxy>octane
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0℃; | 98% |
With pyridine for 2h; | 86% |
With triethylamine In dichloromethane at 15 - 20℃; for 1h; | |
With pyridine | |
With pyridine |
(S)-2-Octanol
2,2,6-trimethyl-4H-1,3-dioxin-4-one
(S)-2-octyl acetoacetate
Conditions | Yield |
---|---|
for 0.1h; microwave irradiation; | 98% |
(S)-2-Octanol
Acetylenedicarboxylic acid
bis[(1S)-1-methylheptyl] acetylenedicarboxylate
Conditions | Yield |
---|---|
With sulfuric acid In tetrahydrofuran for 14h; Reflux; | 97% |
(S)-2-Octanol
benzoic acid
(S)-benzoic acid 1-methylheptyl ester
Conditions | Yield |
---|---|
With cyanomethylenetributyl-phosphorane In benzene at 100℃; for 24h; | 96% |
Conditions | Yield |
---|---|
With azodicarboxylic acid bis(2-methoxyethyl) ester; triphenylphosphine In toluene at 20℃; Product distribution / selectivity; Mitsunobu reaction; | 96% |
With azodicarboxylic acid bis(2-methoxyethyl) ester; triphenylphosphine In toluene at 20℃; for 3.5h; Mitsunobu reaction; Inert atmosphere; stereospecific reaction; | 96% |
With ethyl 2-(3,4-dichlorophenyl)azocarboxylate; triphenylphosphine In toluene at 20℃; for 5h; Mitsunobu Displacement; Inert atmosphere; | 93% |
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran; toluene at 0 - 20℃; for 17.5h; Inert atmosphere; | 96% |
(S)-2-Octanol
(R)-2-chlorooctane
Conditions | Yield |
---|---|
With 1-chloro-1-(dimethylamino)-2-methyl-1-propene In dichloromethane 1.) 0 deg C; 2.) rt., 3h; | 95% |
With trichloroacetonitrile; triphenylphosphine In acetonitrile for 1h; Ambient temperature; | 70% |
With diethyl ether; phosphorus trichloride |
(S)-2-Octanol
methyl 5-chloro-2-fluoro-4-hydroxy-benzoate
(R)-5-chloro-2-fluoro-4-(2-octyloxy)benzoate
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane at 25℃; for 2h; Etherification; | 95% |
Conditions | Yield |
---|---|
for 0.333333h; microwave irradiation; | 95% |
Conditions | Yield |
---|---|
With trimethylamine hydrochloride; triethylamine In dichloromethane at 0℃; for 1h; Inert atmosphere; | 94% |
With trimethylamine hydrochloride; triethylamine In dichloromethane at 0℃; for 2h; Inert atmosphere; | 94% |
With pyridine at 4℃; Inert atmosphere; | 92% |
(S)-2-Octanol
4-(methoxycarbonyloxy)benzoic acid
4-methoxycarbonyloxybenzoic acid (S)-1-methylheptyl ester
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 48h; | 94% |
(S)-2-Octanol
methyl 4-hydroxylbenzoate
methyl 4-{[(1R)-1-methylheptyl]oxy} benzoate
Conditions | Yield |
---|---|
Stage #1: (S)-2-Octanol; methyl 4-hydroxylbenzoate With triphenylphosphine In tetrahydrofuran at 0℃; for 0.25h; Mitsunobu reaction; Stage #2: With di-isopropyl azodicarboxylate In tetrahydrofuran at 0 - 20℃; for 8h; Mitsunobu reaction; | 94% |
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran |
(S)-2-Octanol
benzoic acid
(R)-benzoic acid 1-methylheptyl ester
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran; toluene at 20℃; Product distribution / selectivity; Mitsunobu reaction; | 93% |
With tributylphosphine; 1,1'-azodicarbonyl-dipiperidine In benzene at 60℃; for 24h; | 91% |
With azodicarboxylic acid bis(2-methoxyethyl) ester; triphenylphosphine In diethyl ether at 20℃; for 2h; Mitsunobu reaction; Inert atmosphere; stereospecific reaction; | 89% |
(S)-2-Octanol
N,N-diethyl 4'-bromo-4-methoxybiphenyl-2-carboxamide
(R)-N,N-diethyl 4'-bromo-4-(1-methylheptyloxy)biphenyl-2-carboxamide
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In dichloromethane at 25℃; for 4h; Mitsunobu reaction; | 93% |
(S)-2-Octanol
Conditions | Yield |
---|---|
In chlorobenzene for 0.5h; microwave irradiation; | 92% |
Conditions | Yield |
---|---|
92% |
(S)-2-Octanol
4-Bromobenzoic acid
(S)-1-methylheptyl 4-bromobenzoate
Conditions | Yield |
---|---|
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; | 92% |
4-nitro-phenol
(S)-2-Octanol
(S)-4-(1-methylheptyl)oxy-1-nitrobenzene
Conditions | Yield |
---|---|
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 10 - 20℃; Inert atmosphere; | 91% |
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 18h; Mitsunobu Displacement; | 91% |
With di-isopropyl azodicarboxylate; triphenylphosphine In diethyl ether at 0 - 20℃; | 90% |
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran |
Conditions | Yield |
---|---|
With triethylsilane; ytterbium(III) triflate In 1,2-dichloro-ethane for 4h; Reflux; | 91% |
With triethylsilane; iron(III) chloride In nitromethane at 20℃; for 1h; | 81% |
Conditions | Yield |
---|---|
With potassium fluoride In diethyl ether at 0℃; | 90% |
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