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1,1-Dimethoxycyclohexane cas 933-40-4Appearance:white crystalline powder Storage:Store in dry, dark and ventilated place Package:25KG drum Application:intermediate Transportation:by air, by sea, by express
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Conditions | Yield |
---|---|
With trimethyl orthoformate at 40℃; under 6000480 Torr; for 8h; | 100% |
With chloranil In acetonitrile for 0.5h; Irradiation; | 99% |
With trimethyl orthoformate at 20℃; for 0.5h; | 98% |
Conditions | Yield |
---|---|
With tetra-N-butylammonium tribromide In methanol at 20℃; for 0.33h; | 99% |
Nafion-H In tetrachloromethane | 98% |
With lithium tetrafluoroborate In methanol for 0.333333h; Heating; | 98% |
Conditions | Yield |
---|---|
trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78℃; for 3h; | 89% |
trimethylsilyl trifluoromethanesulfonate In dichloromethane at -78℃; for 3h; | 89% |
With trimethylsilyl trifluoromethanesulfonate |
methanol
heptanal
cyclohexanone
A
cycloxexanone dimethyl ketal
B
1,1-dimethoxyheptane
Conditions | Yield |
---|---|
With CoCl2 for 3.5h; Heating; | A n/a B 88% |
methanol
cyclohexyl-carbamic acid methyl ester
cycloxexanone dimethyl ketal
Conditions | Yield |
---|---|
With tetraethylammonium tosylate electrolysis (15 F/mol, 0.5 A); | 69% |
cyclohexanone
orthoformic acid triethyl ester
trimethyleneglycol
cycloxexanone dimethyl ketal
Conditions | Yield |
---|---|
Stage #1: cyclohexanone; orthoformic acid triethyl ester; trimethyleneglycol With zirconium(IV) chloride In dichloromethane at 20℃; for 1h; Stage #2: With sodium hydroxide | 55% |
Dimethoxymethane
1-(Trimethylsilyloxy)cyclohexene
A
cycloxexanone dimethyl ketal
B
2-(methoxymethyl)cyclohexanone
Conditions | Yield |
---|---|
With 2,6-di-tert-butyl-pyridine; trimethylsilyl trifluoromethanesulfonate In dichloromethane at 16℃; for 10h; | A 20% B 48% |
methanol
cyclohexanone
A
cycloxexanone dimethyl ketal
B
hexanedioic acid dimethyl ester
C
2-methoxycyclohex-2-en-1-one
Conditions | Yield |
---|---|
With cerium(IV) sulphate; oxygen at 50℃; for 8h; Oxidation; acetalization; | A 38% B 35% C 7% |
methanol
cyclohexanone
A
cycloxexanone dimethyl ketal
B
1-(hydroxymethyl)cyclohexanol
Conditions | Yield |
---|---|
With titanium(IV) dichlorodiisopropylate at 20℃; for 72h; UV-irradiation; Inert atmosphere; Overall yield = 38 %; | A 29% B 9% |
methanol
1-iodo-1-cyclohexene
A
cycloxexanone dimethyl ketal
B
1-methoxy-cyclohex-1-ene
C
cyclohexene
Conditions | Yield |
---|---|
With zinc at 40℃; for 10h; Irradiation; | A 8% B 65 % Chromat. C 27% |
With zinc Product distribution; Further Variations:; Reagents; Irradiation; sonication; |
cyclohexene
A
cycloxexanone dimethyl ketal
B
3-methoxycyclohexene
C
1,2-dimethoxycyclohexane
Conditions | Yield |
---|---|
With iodosylbenzene; Dowex 50X8 acidic; FeIIIT4MPyP In methanol at 20℃; for 0.1h; Product distribution; Mechanism; other catalyst: 4-toluenesulphonic acid; | A 20% B 16% C 14% |
methanol
Cyclohexyl-n-butyl ether
A
cycloxexanone dimethyl ketal
B
1,1-dimethoxybutane
C
butanoic acid methyl ester
Conditions | Yield |
---|---|
With tris (2,4-dibromophenyl)amine; sodium methylate; lithium perchlorate at 40℃; electrochem. oxidation; | A 3.6% B 11% C 2.3% |
Conditions | Yield |
---|---|
With hydrogenchloride |
Conditions | Yield |
---|---|
With hydrogenchloride; methanol |
Conditions | Yield |
---|---|
With methanol; tetramethylorthosilicate; phosphoric acid |
Conditions | Yield |
---|---|
at -20℃; Irradiation; |
cyclohexanone
N,N-dimethylformamide dimethyl sulfate adduct
cycloxexanone dimethyl ketal
Conditions | Yield |
---|---|
(i) MeOH, (ii) Et3N, Et2O; Multistep reaction; |
methanol
cyclohexanone
2,2-dimethoxy-propane
cycloxexanone dimethyl ketal
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid Heating; |
methanol
cyclohexene
A
cycloxexanone dimethyl ketal
B
2-methoxycyclohexane
C
3-methoxycyclohexene
Conditions | Yield |
---|---|
With lithium methanolate; lithium perchlorate (electrolysis); |
Conditions | Yield |
---|---|
With sodium tosylate Product distribution; other ethylene ketals, electrochemical transacetalization; var. temperatures and charge; | 76.2 % Chromat. |
With sodium tosylate at 15℃; electrolysis; | 76.5 % Chromat. |
methanol
1-iodo-1-cyclohexene
A
cycloxexanone dimethyl ketal
B
cyclohexene
Conditions | Yield |
---|---|
at 40℃; for 10h; Irradiation; | A 72 % Chromat. B 26 % Chromat. |
Conditions | Yield |
---|---|
With (1,1'-biphenyl)-4,4'-dicarbonitrile Irradiation; | 45 % Chromat. |
1-Methoxybicyclo-<3.1.0>-hexan
cycloxexanone dimethyl ketal
Conditions | Yield |
---|---|
With (1,1'-biphenyl)-4,4'-dicarbonitrile In methanol Product distribution; Mechanism; Irradiation; other deriv. of cyclopropyl ethers; var solvents; |
cyclohexanone
trimethyl orthoformate
A
cycloxexanone dimethyl ketal
B
1-azido-1-methoxycyclohexane
Conditions | Yield |
---|---|
With hydrogen azide; toluene-4-sulfonic acid In dichloromethane for 4h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
Conditions | Yield |
---|---|
With lead(IV) acetate |
hydrogenchloride
methanol
dimethylsulfite
cyclohexanone
cycloxexanone dimethyl ketal
Conditions | Yield |
---|---|
analoge Wirkung des Dimethylsulfits bei der Bildung von Glykosiden; |
methanol
cyclohexanone
A
cycloxexanone dimethyl ketal
B
1-methoxy-cyclohex-1-ene
Conditions | Yield |
---|---|
With 2,3,5,6-tetrachlorobenzene-1,4-diol for 0.5h; Irradiation; | A 73 % Chromat. B 26 % Chromat. |
With C3H6NO9P3(6-)*4H2O*Cl(1-)*Gd(3+)*4H(1+) at 35℃; for 0.25h; Inert atmosphere; |
methanol
cyclohexene
A
cycloxexanone dimethyl ketal
B
cyclohexanone
Conditions | Yield |
---|---|
With carbon dioxide; oxygen; palladium dichloride at 50℃; under 105011 Torr; for 15h; | A 32.4 % Chromat. B n/a |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 85 percent / water; acetone / mesoporous aluminosilicate / 2 h / 55 °C 2: 25 percent / mesoporous aluminosilicate / 6 h / 50 °C View Scheme |
cycloxexanone dimethyl ketal
tert-butylisonitrile
1-methoxycyclohexanecarbonitrile
Conditions | Yield |
---|---|
With titanium tetrachloride at -78 - -30℃; | 100% |
With titanium tetrachloride In dichloromethane at -70 - 20℃; for 3h; | 92% |
titanium tetrachloride In dichloromethane at -70℃; for 0.0833333h; | |
With titanium tetrachloride In dichloromethane at -70 - 20℃; | 1 g |
Conditions | Yield |
---|---|
With trimethylsilan; trimethylsilyl trifluoromethanesulfonate In dichloromethane 0 deg C, 30 min. then 28 deg C, 14 h.; | 100% |
With triethylsilane; Nafion-H (perfluororesinsulfonic acid) In dichloromethane for 4h; Heating; | 91.7 % Chromat. |
Multi-step reaction with 2 steps 1: benzoyl chloride; quinoline / 60 - 70 °C 2: palladium black; diethyl ether / Hydrogenation View Scheme |
cycloxexanone dimethyl ketal
allyl-trimethyl-silane
1-methoxy-1-(2-propenyl)-cyclohexane
Conditions | Yield |
---|---|
With 50 wt% silicomolybdic acid/SiO2 In acetonitrile at 20℃; for 0.16h; Hosomi-Sakurai reaction; | 99% |
With Al-MCM-41 In dichloromethane at 30℃; for 1.5h; Sakurai allylation; Inert atmosphere; | 95% |
With Al-MCM-41 (Si/Al = 48) In dichloromethane at 30℃; for 1.5h; Inert atmosphere; | 95% |
cycloxexanone dimethyl ketal
C60H64N4O16
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 50 - 60℃; for 2h; | 99% |
Conditions | Yield |
---|---|
With water at 80℃; for 0.25h; microwave irradiation; | 99% |
With silica gel; iron(III) chloride at 20℃; for 0.0833333h; | 97% |
With water; Nafion-H In acetone for 0.5h; | 95% |
cycloxexanone dimethyl ketal
isoascorbic acid
5,6-O-Cyclohexylidene-D-isoascorbic acid
Conditions | Yield |
---|---|
With tin(ll) chloride In ethyl acetate for 0.5h; Heating; | 99% |
cycloxexanone dimethyl ketal
3,4-O-cyclohexylidene-6-deoxy-myo-inositol
D-2,3;4,5-di-O-cyclohexylidene-6-deoxy-myo-inositol
Conditions | Yield |
---|---|
With camphor-10-sulfonic acid In N,N-dimethyl-formamide for 12h; Cyclization; | 99% |
1-styrenyloxytrimethylsilane
cycloxexanone dimethyl ketal
Conditions | Yield |
---|---|
With MCM-41 mesoporous silica catalyst In toluene at 0℃; for 12h; Mukaiyama-aldol reaction; | 99% |
With Al-MCM-41 In acetonitrile at 0℃; for 1h; Mukaiyama aldol reaction; Inert atmosphere; | 85% |
With mesoporous aluminosilicate Al-MCM-41 In acetonitrile at 0℃; for 1h; Mukaiyama Aldol Addition; Inert atmosphere; | 85% |
cycloxexanone dimethyl ketal
4-methoxyphenyl α-L-rhamnopyranoside
p-methoxyphenyl 2,3-O-cyclohexylidene-α-L-rhamnopyranoside
Conditions | Yield |
---|---|
camphor-10-sulfonic acid In N,N-dimethyl-formamide at 50℃; for 3h; | 99% |
cycloxexanone dimethyl ketal
2-(3,4-dimethoxyphenyl)ethyl alcohol
6',7'-dimethoxyspiro[cyclohexane-1,1'-isochroman]
Conditions | Yield |
---|---|
With bismuth(lll) trifluoromethanesulfonate; water In toluene at 80℃; oxa Pictet-Spengler reaction; | 99% |
With iron(II) triflate In toluene at 70℃; for 24h; Pictet-Spengler Synthesis; Green chemistry; | 53% |
cycloxexanone dimethyl ketal
3-O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-sn-glycerol
3-O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-1,2-O-cyclohexylidene-sn-glycerol
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid | 98.3% |
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 40℃; under 20 Torr; for 2h; | 98.3% |
cycloxexanone dimethyl ketal
6'-N-(benzyloxyarbonyl)-1,3,3''-tri-N-tosylkanamycin A
6'-N-(benzyloxyarbonyl)-4'',6''-O-cyclohexylidene-1,3,3''-tri-N-tosylkanamycin A
Conditions | Yield |
---|---|
toluene-4-sulfonic acid In N,N-dimethyl-formamide Ambient temperature; | 98% |
cycloxexanone dimethyl ketal
3'-deoxy-1,3,2',6',3''-penta-N-tosylkanamycin B
4'',6''-O-cyclohexylidene-3'-deoxy-1,3,2',6',3''-penta-N-tosylkanamycin B
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 50℃; for 2h; | 98% |
cycloxexanone dimethyl ketal
L-5,6-O-cyclohexylidene-3-deoxy-chiro-inositol
L-1,2;5,6-di-O-cyclohexylidene-3-deoxy-chiro-inositol
Conditions | Yield |
---|---|
With camphor-10-sulfonic acid In N,N-dimethyl-formamide for 12h; Cyclization; | 98% |
Conditions | Yield |
---|---|
With indium In tetrahydrofuran; water at 20℃; for 6h; | 98% |
cycloxexanone dimethyl ketal
1,3,2',7',4"-pentakis-N-(benzyloxycarbonyl)apramycin
Conditions | Yield |
---|---|
Stage #1: cycloxexanone dimethyl ketal; 1,3,2',7',4"-pentakis-N-(benzyloxycarbonyl)apramycin With toluene-4-sulfonic acid; triethylamine In N,N-dimethyl-formamide at 60℃; for 4h; Stage #2: With acetic acid In 1,4-dioxane; water at 20℃; for 18h; | 98% |
methyl 2-desoxy-2-(methoxycarbonylamino)-α-D-glucopyranoside
cycloxexanone dimethyl ketal
methyl 4,6-O-cyclohexylidene-2-deoxy-2-(methoxycarbonyl)amino-α-D-glucopyranoside
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 50℃; under 15 Torr; for 1.5h; | 97% |
cycloxexanone dimethyl ketal
D-gulono-1,4-lactone
2,3:5,6-O-dicyclohexylidene D-gulono-lactone
Conditions | Yield |
---|---|
With 4 A molecular sieve; toluene-4-sulfonic acid In benzene for 10h; Heating; | 97% |
With toluene-4-sulfonic acid In benzene for 10h; Heating; |
cycloxexanone dimethyl ketal
4'',6''-O-Benzylidene-6'-N,4'-O-carbonyl-2',3'-O-cyclohexylidene-1,3,3''-tri-N-tosylkanamycin A
Conditions | Yield |
---|---|
With 5A molecular sieve; trifluoroacetic acid In dichloromethane; N,N-dimethyl-formamide for 6h; Heating; | 97% |
cycloxexanone dimethyl ketal
(2R,3R,4S)-5-Iodo-2,4-dimethyl-hex-5-ene-1,3-diol
(2R,3R)-2-((S)-2-Iodo-1-methyl-allyl)-3-methyl-1,5-dioxa-spiro[5.5]undecane
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate | 97% |
Conditions | Yield |
---|---|
Stage #1: mannitol With toluene-4-sulfonic acid In N,N-dimethyl-formamide Heating; Stage #2: cycloxexanone dimethyl ketal at 60℃; for 1h; Heating; | 96% |
cycloxexanone dimethyl ketal
(3R,5S)-tert-butyl 3,5-dihydroxyhexanoate
Conditions | Yield |
---|---|
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 18h; | 96% |
Conditions | Yield |
---|---|
Heating; | 95% |
With trimethylsilyl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine In dichloromethane for 3h; Ambient temperature; | 94% |
With trimethylsilyl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine In dichloromethane for 3h; Ambient temperature; | 94% |
3-cyano-2H-cycloheptafuran-2-one
cycloxexanone dimethyl ketal
1-Cyano-2,3-tetramethylenazulen
Conditions | Yield |
---|---|
at 160 - 190℃; | 95% |
cycloxexanone dimethyl ketal
N,N',N'',N'''-tetra(benzyloxycarbonyl)neamine
1,3,2',6'-tetrakis(N-benzyloxycarbonyl)-5,6-O-cyclohexylideneneamine
Conditions | Yield |
---|---|
Stage #1: cycloxexanone dimethyl ketal; N,N',N'',N'''-tetra(benzyloxycarbonyl)neamine With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 50℃; for 5h; Inert atmosphere; Stage #2: In methanol; N,N-dimethyl-formamide at 50℃; for 1h; Stage #3: With triethylamine In methanol; N,N-dimethyl-formamide at 20℃; | 95% |
With 5A molecular sieve; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid 1.) DMF, CH2Cl2, 6 h, reflux; 2.) ethanol, 25 deg C, 16 h; Yield given. Multistep reaction; |
cycloxexanone dimethyl ketal
1,3,2',3''-tetrakis(N-benzyloxycarbonyl)-3',4'-dideoxykanamycin C
1,3,2',3''-tetrakis(N-benzyloxycarbonyl)-4'',6''-O-cyclohexylidene-3',4'-dideoxykanamycin C
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In N,N-dimethyl-formamide for 16h; Ambient temperature; | 95% |
cycloxexanone dimethyl ketal
(3R,4S,5R)-3,4,5-trihydroxycyclohexanone ethylene dithioacetal
Conditions | Yield |
---|---|
With sulfuric acid In N,N-dimethyl-formamide for 24h; Ambient temperature; | 95% |
With sulfuric acid In N,N-dimethyl-formamide | 85% |
With sulfuric acid In N,N-dimethyl-formamide for 6h; | 85% |
cycloxexanone dimethyl ketal
Conditions | Yield |
---|---|
With sulfuric acid In N,N-dimethyl-formamide | 95% |
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