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% |
The IUPAC name of Cyclohexane,1,1-dimethoxy- is 1,1-dimethoxycyclohexane. With the CAS registry number 933-40-4, it is also named as Cyclohexanone, dimethyl acetal. In addition, its molecular formula is C8H16O2 and molecular weight is 144.21.
The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.30; (2)ACD/LogD (pH 5.5): 1.3; (3)ACD/LogD (pH 7.4): 1.3; (4)ACD/BCF (pH 5.5): 5.7; (5)ACD/BCF (pH 7.4): 5.7; (6)ACD/KOC (pH 5.5): 120.94; (7)ACD/KOC (pH 7.4): 120.94; (8)#H bond acceptors: 2; (9)#Freely Rotating Bonds: 2; (10)Polar Surface Area: 18.46Å2; (11)Index of Refraction: 1.435; (12)Molar Refractivity: 40.52 cm3; (13)Molar Volume: 155.2 cm3; (14)Polarizability: 16.06x10-24cm3; (15)Surface Tension: 28.2 dyne/cm; (16)Enthalpy of Vaporization: 38.25 kJ/mol; (17)Boiling Point: 162.3 °C at 760 mmHg; (18)Vapour Pressure: 2.84 mmHg at 25 °C.
Preparation of Cyclohexane,1,1-dimethoxy-: this chemical can be prepared by Cyclohexanone and Methanol.
This reaction needs I2. The reaction time is 1 hour. The yield is about 90%.
Uses of Cyclohexane,1,1-dimethoxy-: it can be used to produce 1-Methoxy-cyclohexene.
This reaction needs Benzoyl chloride and quinoline at temperature of 60 - 70 °C.
When you are using this chemical, please be cautious about it as the following: it is flammable. In use, it may form inflammable/explosive vapour-air mixture. When you are using it, please keep away from sources of ignition and use only in well ventilated areas.
You can still convert the following datas into molecular structure:
(1)SMILES: O(C)C1(OC)CCCCC1
(2)InChI: InChI=1/C8H16O2/c1-9-8(10-2)6-4-3-5-7-8/h3-7H2,1-2H3
(3)InChIKey: XPIJMQVLTXAGME-UHFFFAOYAO
(4)Std. InChI: InChI=1S/C8H16O2/c1-9-8(10-2)6-4-3-5-7-8/h3-7H2,1-2H3
(5)Std. InChIKey: XPIJMQVLTXAGME-UHFFFAOYSA-N
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