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inquiryConditions | Yield |
---|---|
Stage #1: Methyl oleate With ozone In dichloromethane at -78℃; Stage #2: With triphenylphosphine In dichloromethane at -78 - 23℃; for 18h; | A 100% B 100% |
With N-methyl-2-indolinone; ozone at 0℃; | A 74% B 96% |
With ozone; acetic acid; zinc 1.) MeOH, CH2Cl2, -78 deg C, 2.) MeOH, CH2Cl2, 30 min; Multistep reaction. Yields of byproduct given; |
Conditions | Yield |
---|---|
With 2-pyridylpropylimine rhodium(I)chlorocarbonyl; hydrogen In toluene at 95℃; Catalytic behavior; Reagent/catalyst; Pressure; Temperature; Autoclave; chemoselective reaction; | 100% |
With hydrogen In dichloromethane at 45℃; under 51716.2 Torr; for 16h; Autoclave; Inert atmosphere; Green chemistry; regioselective reaction; | 100% |
With hydrogen In cyclohexane at 120℃; under 37503.8 Torr; for 4h; Autoclave; | 99% |
Conditions | Yield |
---|---|
With sodium periodate In 1,4-dioxane; water at 20℃; for 1h; | A n/a B 100% |
Conditions | Yield |
---|---|
With hydrogen In water at 100℃; under 15001.5 Torr; for 12h; Autoclave; Green chemistry; regioselective reaction; | 99.5% |
With hydrogen; 4,5-bis(9-dibenzo[b,d]phospholyl)-2,7-di-tert-butyl-9,9-dimethylxanthene; (2,2,6,6-tetramethyl-3,5-heptanedionate)Rh(CO)2 In toluene at 80℃; under 15001.2 Torr; for 1h; Yield given; | |
With hydrogen; 2,2'-bis(di(3,4,5-F-phenyl)phosphanylmethyl)-1,1'-binaphthyl; acetylacetonatodicarbonylrhodium(l) In methoxybenzene; toluene at 120℃; under 7500.6 Torr; for 16h; |
Conditions | Yield |
---|---|
With 4-methoxy-TEMPO; sodium hypochlorite; potassium bromide In dichloromethane; water at 0℃; for 0.05h; Mechanism; Product distribution; pH = 8.6; other primary and secondary alcohols, var. temp., time, pH, and catalytic species; | 98% |
With tert.-butylhydroperoxide In water at 60℃; for 3h; | 98% |
With 4-methoxy-TEMPO; sodium hypochlorite; potassium bromide In dichloromethane; water at 0℃; for 0.05h; pH = 8.6; | 92% |
2-(n-Octyl)-1,3-dithiane
nonan-1-al
Conditions | Yield |
---|---|
With tri(p-tolyl)amine; lithium perchlorate; sodium hydrogencarbonate In water; acetonitrile at 20℃; electrolysis; | 97% |
With periodic acid In tetrahydrofuran; diethyl ether for 0.0833333h; Ambient temperature; | 91% |
Conditions | Yield |
---|---|
With [bis(acetoxy)iodo]benzene In dichloromethane at 25℃; for 2.5h; Inert atmosphere; | 97% |
With sodium periodate; sodium hydrogencarbonate In water; acetonitrile at 20℃; for 1.5h; | |
With N-Bromosuccinimide; (oxybis(2,1-phenylene))bis(diphenylbismuthane); potassium carbonate In [D3]acetonitrile at 23℃; for 1h; Schlenk technique; | 70 %Spectr. |
nonan-1-al
Conditions | Yield |
---|---|
With hydrogen fluoride In acetonitrile at 20℃; | 96% |
epoxidized methyl oleate
A
nonan-1-al
B
methyl ester of azelaic acid aldehyde
Conditions | Yield |
---|---|
With periodic acid In diethyl ether | A n/a B 95% |
With periodic acid for 0.05h; Product distribution; Ambient temperature; | |
Multi-step reaction with 2 steps 1: sulfuric acid / acetic acid; acetonitrile; water / 16 h / 20 °C 2: sodium periodate; sodium hydrogencarbonate / acetic acid; acetonitrile; water / 1.5 h / 20 °C View Scheme |
Conditions | Yield |
---|---|
With oxygen; ozone; 4-methylmorpholine N-oxide In dichloromethane at 0℃; | 94% |
With ozone; 4-methylmorpholine N-oxide In dichloromethane at 0 - 20℃; | 94% |
With sodium periodate; 1,4-diazobicyclo<2.2.2>octane quaternized with chloromethylated styrene-divinylbenzene copolymer*OsO4 In 1,4-dioxane; water for 0.5h; Ambient temperature; | 100 % Chromat. |
Formic acid (E)-non-1-enyl ester
nonan-1-al
Conditions | Yield |
---|---|
With hydrogenchloride In tetrahydrofuran; water for 23h; Ambient temperature; | 94% |
oct-1-ene
carbon monoxide
A
nonan-1-al
B
2-methyl-1-octanal
Conditions | Yield |
---|---|
With hydrogen In cyclohexane at 120℃; under 37503.8 Torr; for 3h; Autoclave; | A 93% B 7% |
With hydrogen; 1-octyl-3-methyl-imidazolium bromide In water at 100℃; under 15001.5 Torr; for 3h; Product distribution; Further Variations:; Reagents; reaction time; | A 91.5% B 5.7% |
With hydrogen In n-heptane; toluene at 90℃; under 37503.8 Torr; for 20h; | A n/a B 91% |
2-methyl-undec-2-ene
nonan-1-al
Conditions | Yield |
---|---|
With ozone In dichloromethane at -78℃; | 93% |
With ozone In dichloromethane at -78℃; | 93% |
Conditions | Yield |
---|---|
With sulfuric acid for 10h; Ambient temperature; | 92% |
With ammonium cerium(IV) nitrate In methanol; water at 20℃; for 0.166667h; Ring cleavage; | 91% |
With dimethylboron bromide; sodium hydrogencarbonate 1) CH2Cl2, -78 deg C, 1h, 2) THF, 5 min; Yield given. Multistep reaction; |
oct-1-ene
carbon monoxide
A
nonan-1-al
B
octane
C
2-octene
Conditions | Yield |
---|---|
With (acetylacetonato)dicarbonylrhodium (l); 2,2'-bis((dipyrrolylphosphinooxy)methyl)-1,1'-(±)-biphenyl; hydrogen In toluene at 80℃; under 11251.1 Torr; for 1h; Pressure; Reagent/catalyst; Temperature; regioselective reaction; | A 91.9% B n/a C n/a |
1,1-dimethoxynonane
nonan-1-al
Conditions | Yield |
---|---|
With dimethylboron bromide In dichloromethane; 1,2-dichloro-ethane at -78℃; for 1h; | 91% |
With guanidine hydrochloride; acetyl chloride for 3h; Ambient temperature; | 85% |
With diphosphorus tetraiodide; propene In dichloromethane at 20℃; for 0.2h; | 64% |
trimethylsilyloxy-nonane
nonan-1-al
Conditions | Yield |
---|---|
With ammonium cerium(IV) nitrate; HZSM-5 zeolite In water for 0.133333h; microwave irradiation; | 91% |
With chromium(VI) oxide In pyridine; dichloromethane at 0℃; for 1h; |
nonan-1-al
Conditions | Yield |
---|---|
With periodic acid In tetrahydrofuran; diethyl ether for 0.166667h; Ambient temperature; | 90% |
Conditions | Yield |
---|---|
Stage #1: cis-Octadecenoic acid With ozone In dichloromethane at -78℃; Stage #2: With dimethylsulfide In dichloromethane at 20℃; for 3h; | A n/a B 90% |
Stage #1: cis-Octadecenoic acid With ozone at 95℃; Stage #2: With hydrogen at 30℃; under 3750.38 Torr; palladium-coated film reactor; | A n/a B 48.7% |
With 1-carboxymethyl-3-methylimidazol-3-ium hydrogen sulfate; dihydrogen peroxide at 5℃; for 5h; | |
Multi-step reaction with 3 steps 1: [((S,S)-N,N′-bis(2-pyridylmethyl)-(S,S)-2,2′-bipyrrolidine)FeII(OTf)2]; dihydrogen peroxide / acetonitrile / 2.5 h / 0 °C 2: sulfuric acid / acetonitrile; water / 16 h / 20 °C 3: sodium periodate; sodium hydrogencarbonate / acetonitrile; water / 1.5 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: potassium hydroxide; potassium permanganate / water / 0.25 h / 0 - 50 °C 2: sodium periodate; tetra(n-butyl)ammonium hydrogen sulfate / water; dichloromethane / 20 °C View Scheme |
Conditions | Yield |
---|---|
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In water; toluene at 90℃; for 0.5h; Microwave irradiation; Sealed vial; | 90% |
octadec-9-enoic acid methyl ester
A
nonan-1-al
B
methyl ester of azelaic acid aldehyde
Conditions | Yield |
---|---|
With ozone; triphenylphosphine In dichloromethane at -78℃; for 24h; Inert atmosphere; | A 90% B 75% |
With ozone; potassium iodide In water; tert-butyl alcohol for 1h; | |
Stage #1: octadec-9-enoic acid methyl ester With oxygen; ozone In neat (no solvent) at 25℃; Stage #2: With 5%-palladium/activated carbon; hydrogen at 20℃; for 1h; Solvent; Temperature; |
nonan-1-al
Conditions | Yield |
---|---|
With dimethyl sulfoxide at 20℃; for 17h; | 90% |
Conditions | Yield |
---|---|
With sodium periodate; phosphoric acid; sodium carbonate | A 61.5% B 89% |
With sodium periodate; sodium hydrogencarbonate In water; acetic acid; acetonitrile at 20℃; for 24h; |
nonanal semicarbazone
nonan-1-al
Conditions | Yield |
---|---|
With K-10 clay-supported Fe(NO3)3 ("clayfen" reagent) In dichloromethane for 1.16667h; Ambient temperature; | 89% |
Conditions | Yield |
---|---|
With water; ruthenium-based phosphine complex In acetone at 120℃; for 26h; | 89% |
With [CpRu(6-Ph2P-Py-2-yl)(MeCN)][PF6(1-)]; water In acetone at 70℃; for 3h; | 99.9 % Spectr. |
With water; [cyclopentadienylruthenium(II) bis(2-diphenylphosphino-6-t-butylpyridine)(acetonitrile)]CF3SO3 In acetone at 70℃; Kinetics; |
Conditions | Yield |
---|---|
With 3-butyl-4,5-dimethylthiazol-3-ium trifluoromethanesulfonate; potassium carbonate at 180℃; under 7.50075 Torr; Inert atmosphere; | 88% |
Conditions | Yield |
---|---|
With diisobutylaluminium hydride In dichloromethane at -78℃; for 0.5h; Inert atmosphere; | 88% |
trans-2-Octene
carbon monoxide
A
nonan-1-al
B
2-ethylheptanal
C
2-methyl-1-octanal
D
2-n-propylhexanal
Conditions | Yield |
---|---|
With zinc 5,10,15,20-tetraphenylporphyrin; N-ethyl-N,N-diisopropylamine; tri(pyridin-3-yl)phosphine; acetylacetonatodicarbonylrhodium(l) In toluene at 25℃; for 73h; Product distribution; Further Variations:; Catalysts; Temperatures; | A 0.7% B 87.8% C 9.4% D 0.5% |
With 25,26,27,28-tetrakis(hydroxy)calix[4]arene; hydrogen; phosphan; acetylacetonatodicarbonylrhodium(l) In water at 140℃; under 30003 Torr; for 12h; Product distribution; | |
With (acetylacetonato)dicarbonylrhodium (l); rac-3-methyl-2-(2-methylnaphthalen-1-yl)-4-phenyl-5,6-dihydrobenzo[1,2-h]phosphinoline; hydrogen In toluene at 80℃; under 15001.5 Torr; for 90h; Reagent/catalyst; Autoclave; |
trans-4-Octene
dichloromethane
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
nonan-1-al
Conditions | Yield |
---|---|
Stage #1: trans-4-Octene; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane With triphenylphosphine; chlorobis(ethylene)rhodium(I) dimer In dichloromethane for 0.5h; Stage #2: dichloromethane With n-butyllithium In tetrahydrofuran at -78 - 20℃; Stage #3: With dihydrogen peroxide; sodium carbonate In tetrahydrofuran; water at 0 - 20℃; | 86% |
cis-2-octene
dichloromethane
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
nonan-1-al
Conditions | Yield |
---|---|
Stage #1: cis-2-octene; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane With triphenylphosphine; chlorobis(ethylene)rhodium(I) dimer In dichloromethane for 0.5h; Stage #2: dichloromethane With n-butyllithium In tetrahydrofuran at -78 - 20℃; Stage #3: With dihydrogen peroxide; sodium carbonate In tetrahydrofuran; water at 0 - 20℃; | 86% |
Conditions | Yield |
---|---|
With tri-n-butyl-tin hydride In methanol; diethyl ether for 4h; Reduction; Heating; | 100% |
With hydrogenchloride; tetrahydrogenoboratebis(triphenylphosphine)copper(I) In dichloromethane | 94% |
With hydrogenchloride; samarium In tetrahydrofuran at 20℃; | 94% |
Conditions | Yield |
---|---|
at 25℃; | 100% |
Conditions | Yield |
---|---|
With indium In water at 20℃; for 3h; Addition; | 100% |
With indium In N,N-dimethyl-formamide for 3h; Ambient temperature; | 93% |
nonan-1-al
N-benzyl-N-(1-octynyl)-p-toluenesulfonamide
Conditions | Yield |
---|---|
Stage #1: N-benzyl-N-(1-octynyl)-p-toluenesulfonamide With titanium(IV) isopropylate; isopropylmagnesium chloride Stage #2: nonan-1-al Stage #3: With hydrogen cation Acid hydrolysis; Further stages.; | 100% |
nonan-1-al
diphenyl acetylene
N-benzyl-N-ethynyl-4-methyl-benzenesulfonamide
Conditions | Yield |
---|---|
Stage #1: diphenyl acetylene With titanium(IV) isopropylate; isopropylmagnesium bromide In diethyl ether at -78 - -50℃; for 2.5h; Stage #2: N-benzyl-N-ethynyl-4-methyl-benzenesulfonamide In diethyl ether at -50℃; for 4h; Stage #3: nonan-1-al In diethyl ether at -50 - 20℃; | 100% |
Multistep reaction.; | 100% |
Conditions | Yield |
---|---|
Stage #1: acetoacetic acid methyl ester With sodium hydride In tetrahydrofuran at 0℃; for 0.166667h; Stage #2: With n-butyllithium In tetrahydrofuran; hexane at 20℃; for 0.333333h; Stage #3: nonan-1-al In tetrahydrofuran; hexane at -78 - 20℃; for 1.08333h; | 100% |
Stage #1: acetoacetic acid methyl ester With sodium hydride In tetrahydrofuran; mineral oil at 0 - 5℃; for 0.166667h; Stage #2: With n-butyllithium In tetrahydrofuran; mineral oil at 5℃; for 0.166667h; Stage #3: nonan-1-al In tetrahydrofuran; mineral oil at 5 - 10℃; for 0.5h; |
Conditions | Yield |
---|---|
With anthranilic acid In dichloromethane at 60℃; for 24h; Molecular sieve; | 100% |
nonan-1-al
Conditions | Yield |
---|---|
Stage #1: (3S)-5,7-dimethoxy-4-methyl-3-(1-oxopropyl)phthalide With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.5h; Inert atmosphere; Stage #2: nonan-1-al In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; | 100% |
Conditions | Yield |
---|---|
With Oxone In N,N-dimethyl-formamide at 20℃; for 3h; | 99% |
With Oxone; ethylenediaminetetraacetic acid; sodium hydrogencarbonate In water; acetone at 22℃; for 1.5h; Oxidation; | 86% |
With NAD; Geotrichum candidum aldehyde dehydrogenase In aq. buffer at 40℃; for 3h; pH=7.2; Green chemistry; Enzymatic reaction; | 43% |
Conditions | Yield |
---|---|
With n-butyllithium In tetrahydrofuran | 99% |
Conditions | Yield |
---|---|
In tetrahydrofuran; diethyl ether at -78 - 20℃; Inert atmosphere; | 99% |
With magnesium bromide diethyl etherate In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; | 90% |
In tetrahydrofuran 1.) RT, overnight, 2.) reflux, 6 h; | 84% |
nonan-1-al
3-methoxycarbonyl-2H-cyclohepta[b]furan-2-one
Conditions | Yield |
---|---|
With morpholine In ethanol for 4h; Heating; | 99% |
nonan-1-al
trimethylsilylacetylene
(+/-)-1-trimethylsilyl-1-undecyn-3-ol
Conditions | Yield |
---|---|
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran; hexane at -75 - -10℃; for 0.5h; Inert atmosphere; Stage #2: nonan-1-al In tetrahydrofuran; hexane at -78 - 20℃; for 1h; | 99% |
With ethylmagnesium bromide In tetrahydrofuran for 2h; Heating; | 74% |
With n-butyllithium In tetrahydrofuran; hexane 1.) -85 deg C, 15 min, 2.) -85 deg C to 0 deg C, 2 h; | |
Stage #1: trimethylsilylacetylene With n-butyllithium In tetrahydrofuran; hexane at 0℃; for 0.5h; Inert atmosphere; Stage #2: nonan-1-al In tetrahydrofuran; hexane at -78℃; for 0.5h; Inert atmosphere; |
Conditions | Yield |
---|---|
With 1,2-dichloro-benzene at 140 - 170℃; for 0.166667h; | 99% |
nonan-1-al
allyltributylstanane
dodec-1-en-4-ol
Conditions | Yield |
---|---|
With 4-nitro-benzoic acid In acetonitrile at 25℃; for 10h; | 99% |
With cerium(III) chloride; sodium iodide In acetonitrile at 20℃; for 22h; | 91% |
With aluminum oxide; cerium(III) chloride; sodium iodide at 50℃; for 18h; | 85% |
Conditions | Yield |
---|---|
With 1,3-dimethylbenzimidazolium Iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene In 1,4-dioxane for 3h; Heating; | 99% |
With C15H22N3O2(1+)*Cl(1-); 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 0℃; for 5h; Inert atmosphere; | 79% |
With 3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide; triethylamine In ethanol at 80℃; for 4h; | 73% |
Conditions | Yield |
---|---|
indium In water Ambient temperature; | 99% |
With gallium; indium In tetrahydrofuran at 25℃; for 1h; | 75% |
Conditions | Yield |
---|---|
In water Ambient temperature; | 99% |
nonan-1-al
hydrogen cyanide
2-amino-6-methylphenol
1-(2-hydroxy-6-methylphenyl)amino-3-methylbutane-1-carbonitrile
Conditions | Yield |
---|---|
((R)-3,3'-dibromo-1,1'-bi-2-naphtholato){Zr(CN)(N-methylimidazole)((R)-6,6'-dibromo-1,1'-bi-2-naphtholato)}2 In dichloromethane at -45℃; 5 mol % catalyst; | 99% |
((R)-3,3'-dibromo-1,1'-bi-2-naphtholato){Zr(CN)(N-methylimidazole)((R)-6,6'-dibromo-1,1'-bi-2-naphtholato)}2 In dichloromethane at -45℃; 5 mol % catalyst; | 94% |
Conditions | Yield |
---|---|
With N,N-dimethylbenzylamine prolinol trimethylsilyl ether; benzoic acid In water at 20℃; for 22h; Michael addition; optical yield given as %ee; enantioselective reaction; | 99% |
With N,N-dimethylbenzylamine prolinol trimethylsilyl ether; C15H19N2O2(1+)*F6P(1-) In water at 20℃; for 20h; Michael condensation; optical yield given as %ee; enantioselective reaction; | 98% |
Stage #1: nonan-1-al With C16H27N5OSi; sodium hydrogencarbonate In sodium chloride at 20℃; for 0.166667h; Michael addition; Stage #2: nitrostyrene In sodium chloride at 20℃; for 48h; Michael addition; optical yield given as %ee; diastereoselective reaction; | 59% |
Conditions | Yield |
---|---|
With C36H44N4O4S2; copper(I) bromide In methanol at 20℃; for 36h; Henry reaction; Inert atmosphere; optical yield given as %ee; enantioselective reaction; | 99% |
With C13H24Cl2CuN2; triethylamine In tetrahydrofuran; nitromethane at -20℃; for 49h; Henry Nitro Aldol Condensation; enantioselective reaction; | 98% |
With (R)-N-methyl-1',2',3',4'-tetrahydro-1,1'-bisisoquinoline; copper(l) chloride In di-isopropyl ether at 0℃; for 20h; Henry reaction; optical yield given as %ee; enantioselective reaction; | 75% |
With C19H17N; copper(l) chloride In 1,2-dichloro-ethane at 0℃; for 48h; Henry reaction; optical yield given as %ee; enantioselective reaction; | 72% |
nonan-1-al
N-(1,1-diphenyl-3-butenyl)amine
Conditions | Yield |
---|---|
at 20℃; for 6h; Aza-Cope Rearrangement; Molecular sieve; | 99% |
furan
nonan-1-al
<1(R,S),5(R,S)>-6(R,S)-n-octyl-2,7-dioxabicyclo<3.2.0>hept-3-ene
Conditions | Yield |
---|---|
at -20℃; for 9.5h; Irradiation; | 98.6% |
Conditions | Yield |
---|---|
With thionyl chloride In chloroform for 0.5h; Heating; | 98% |
Conditions | Yield |
---|---|
98% |
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