2,3-dioxabicyclo[2.2.2]octane
4-hydroxycyclohexanone
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 72h; Kornblum-DeLaMare rearrangement; | 100% |
Multi-step reaction with 3 steps 1: 49 percent / n-BuLi / diethyl ether / -78 °C 2: 47 percent / CH2Cl2 / 1 h / 0 - 20 °C 3: 75 percent / potassium t-butoxide / tetrahydrofuran / 0.25 h View Scheme |
4,4-ethylenedioxycyclohexan-1-ol
4-hydroxycyclohexanone
Conditions | Yield |
---|---|
With water; toluene-4-sulfonic acid for 2h; Heating; | 99% |
With hydrogenchloride In water; acetone at 20℃; for 28h; | 99% |
With ammonium cerium(IV) nitrate; water In acetonitrile at 60℃; for 0.416667h; pH=8; Hydrolysis; | 92% |
4-methoxy-phenol
4-hydroxycyclohexanone
Conditions | Yield |
---|---|
With potassium hydroxide; samarium diiodide In tetrahydrofuran; water for 0.116667h; Ambient temperature; | 97% |
1,4-Cyclohexanedione
4-hydroxycyclohexanone
Conditions | Yield |
---|---|
With [(1S,2S)-N-(p-toluensulfonyl)-1,2-diphenylethanediamine](p-cymene)ruthenium (I); formic acid; triethylamine In acetonitrile at 20℃; | 96% |
With Candida parapsilosis ATCC 7330 whole cells In ethanol; water at 25℃; for 8h; pH=6.8; Microbiological reaction; regioselective reaction; | 63% |
With sodium tetrahydroborate In methanol at -20℃; | 60% |
With keto reductases from Lactobacillus kefir; nicotinamide adenine dinucleotide phosphate; isopropyl alcohol In aq. phosphate buffer at 30℃; for 12h; pH=7; Reagent/catalyst; pH-value; Enzymatic reaction; |
Conditions | Yield |
---|---|
With sodium bromate; sodium hydrogensulfite In water; acetonitrile at 20℃; for 6h; Oxidation; | A 1% B 93% |
With sodium bromate; sodium hydrogensulfite In water; acetonitrile at 20℃; for 2h; Oxidation; | A 78% B 10% |
With 2O34W9Zn(12-)*W(6+)*3Zn(2+)*2H2O; dihydrogen peroxide In water; acetonitrile at 135℃; under 2250.23 Torr; for 0.25h; Microwave irradiation; | A n/a B 58% |
1,4-Cyclohexanediol
4-hydroxycyclohexanone
Conditions | Yield |
---|---|
With sodium bromate; ammonium cerium(IV) nitrate In water; acetonitrile | 92% |
With sodium bromate; ammonium cerium (IV) nitrate In water; acetonitrile for 2.5h; Reflux; | 91% |
With calcium hypochlorite; potassium bromide In water; acetic acid at 0℃; for 3h; | 88% |
3-(1-phenyl-vinyl)-1,2,5-trioxa-spiro[5.5]undecan-9-ol
4-hydroxycyclohexanone
Conditions | Yield |
---|---|
With N-benzyl-trimethylammonium hydroxide In tetrahydrofuran at 20℃; for 1h; | 86% |
4-hydroxycyclohexanone
Conditions | Yield |
---|---|
With methanol; Montmorillonite K-10 clay at 20℃; Methanolytic deprotection; | 85% |
4-hydroxy-1-methoxy-1-cyclohexene
4-hydroxycyclohexanone
Conditions | Yield |
---|---|
With hydrogenchloride at 50℃; for 0.75h; | 82% |
succinic acid methyl ester 3-(1-phenylvinyl)-1,2,5-trioxaspiro[5.5]undec-9-yl ester
4-hydroxycyclohexanone
Conditions | Yield |
---|---|
With N-benzyl-trimethylammonium hydroxide In tetrahydrofuran at 20℃; for 1h; | 82% |
hydroquinone
4-hydroxycyclohexanone
Conditions | Yield |
---|---|
With sodium formate; sodium hydroxide In water at 120℃; pH=12; | 82% |
With 5% palladium on Al2O3; hydrogen In 1,2-dichloro-ethane at 60℃; under 3750.38 Torr; for 24h; chemoselective reaction; | 50% |
With hydrogen; palladium In water at 80℃; under 750.075 Torr; for 6h; Sealed; |
4-hydroxycyclohexanone
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran for 0.25h; | 75% |
1,4-bis(trimethylsilyloxy)cyclohex-1-ene
A
4-hydroxycyclohexanone
B
4-(trimethylsiloxy)cyclohexanone
Conditions | Yield |
---|---|
With methanol; biphenyl; 1-Cyanonaphthalene In acetonitrile Product distribution; Mechanism; Ambient temperature; Irradiation; var. temp., no irradiation; 1-(trimethylsiloxy)cyclohexene; | A n/a B 63% |
cyclohexanedione monoethylene ketal
4-hydroxycyclohexanone
Conditions | Yield |
---|---|
Stage #1: cyclohexanedione monoethylene ketal With methanol; sodium tetrahydroborate at 0 - 20℃; for 2h; Stage #2: With hydrogenchloride; water In tetrahydrofuran at 20℃; for 18h; | 62% |
Multi-step reaction with 2 steps 1: 98 percent / sodium borohydride / methanol / 1 h 2: 78 percent / HCl View Scheme | |
Multi-step reaction with 2 steps 1: NaBH4 / ethanol / 3 h / 20 °C 2: ceric ammonium nitrate / acetonitrile; H2O / 0.5 h / 70 °C View Scheme |
cis-(3R)-4-benzoyl-3-methyl-1-oxa-4-azaspiro[4.5]decane-8-ol
4-hydroxycyclohexanone
Conditions | Yield |
---|---|
mildly acidic conditions; | 59% |
2,3-dioxabicyclo<2.2.2>octane
A
ethene
B
butanedial
C
cis-1,4-cyclohexanediol
D
4-hydroxycyclohexanone
Conditions | Yield |
---|---|
With tris(triphenylphosphine)ruthenium(II) chloride In dichloromethane at 50℃; for 2h; Product distribution; ruthenium(II) catalyzed reaction of 1,4-endoperoxide; | A 43% B 19% C 17% D 11% |
With tris(triphenylphosphine)ruthenium(II) chloride In dichloromethane at 50℃; for 2h; Title compound not separated from byproducts; | A 43 % Chromat. B 19 % Spectr. C 17 % Chromat. D 11 % Chromat. |
2,3-dioxabicyclo<2.2.2>octane
A
butanedial
B
cis-1,4-cyclohexanediol
C
4-hydroxycyclohexanone
D
1,4-Cyclohexanedione
Conditions | Yield |
---|---|
With cobalt(II) 5,10,15,20-tetraphenylporphyrin In chloroform at 60℃; for 11h; Further byproducts given; | A 21% B 28% C 17% D 5% |
4-(1-oxoethyl)-1-cyclohexanone
4-hydroxycyclohexanone
Conditions | Yield |
---|---|
With sulfuric acid; water | |
With sodium hydroxide; water |
2,3-dioxabicyclo<2.2.2>octane
A
cis-1,4-cyclohexanediol
B
4-hydroxycyclohexanone
C
1,4-Cyclohexanedione
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0) In dichloromethane at 60℃; for 5h; Product distribution; other reagent; | A 39 % Chromat. B 44 % Chromat. C 4 % Chromat. |
(1S,4R)-Cyclohex-2-ene-1,4-diol
A
4-hydroxy-2-cyclohexenone
B
1,4-Cyclohexanediol
C
4-hydroxycyclohexanone
Conditions | Yield |
---|---|
ruthenium In tetrahydrofuran at 65℃; for 15h; Yield given. Yields of byproduct given; | |
ruthenium In tetrahydrofuran at 60℃; for 15h; Yield given. Yields of byproduct given; |
Conditions | Yield |
---|---|
With hydrogen; silica gel; nickel In isopropyl alcohol at 100℃; under 4650.4 Torr; Product distribution; Kinetics; various catalyst, var. temp., var. of hydrogen pressure, var. of substrate concentr.; | A n/a B 87 % Chromat. |
With hydrogen; palladium/alumina at 130℃; under 22502.3 Torr; Conversion of starting material; | |
With Zr -F-100 In isopropyl alcohol at 82℃; for 6h; Reagent/catalyst; | |
With nicotinamide adenine dinucleotide phosphate; isopropyl alcohol In aq. phosphate buffer at 30℃; for 12h; pH=7; Enzymatic reaction; |
1,4-Cyclohexanedione
A
1,4-Cyclohexanediol
B
4-hydroxycyclohexanone
C
cyclohexanone
D
cyclohexanol
Conditions | Yield |
---|---|
With hydrogen; palladium In tert-butyl alcohol at 30℃; Product distribution; further catalyst; | |
With hydrogen; palladium In tert-butyl alcohol at 30℃; Yield given. Yields of byproduct given; |
(8-hydroxy-1-oxa-4-aza-spiro[4.5]dec-4-yl)-phenyl-methanone
4-hydroxycyclohexanone
Conditions | Yield |
---|---|
With IR 120 (H(+)-form In acetonitrile Hydrolysis; Title compound not separated from byproducts; |
4-hydroxycyclohexanone
Conditions | Yield |
---|---|
With methanol; sodium methylate |
cyclohexanol
A
hexanedial
B
3-hydroxycyclohexanone
C
4-hydroxycyclohexanone
D
cyclohexanone
Conditions | Yield |
---|---|
With air; methyl nitrite; nitrogen(II) oxide at 24.85℃; under 760 Torr; Kinetics; Product distribution; |
4-hydroxycyclohexanone
Conditions | Yield |
---|---|
With ethanol; Raney nickel W-2 at 20℃; for 1h; |
cyclohexanol
A
cyclohexane-1,4-diol
B
cis-1,4-cyclohexanediol
C
4-hydroxycyclohexanone
Conditions | Yield |
---|---|
With oxygen at 129.85℃; Kinetics; Product distribution; |
3-(1-Phenyl-vinyl)-1,2,5-trioxaspiro[5.5]undec-9-one
4-hydroxycyclohexanone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 96 percent / NaBH4 / methanol / 0.5 h / 0 °C 2: 86 percent / Triton B / tetrahydrofuran / 1 h / 20 °C View Scheme |
(1R,1S)-2,3-dioxabicyclo[2.2.2]oct-5-ene
4-hydroxycyclohexanone
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 48 percent / n-BuLi / diethyl ether / -78 °C 2: 83 percent / H2 / Pd/C / ethyl acetate / 7 h 3: 47 percent / CH2Cl2 / 1 h / 0 - 20 °C 4: 75 percent / potassium t-butoxide / tetrahydrofuran / 0.25 h View Scheme |
1-(6-bromo-2-pyridyl)-1-methyl-hydrazine
4-hydroxycyclohexanone
C12H16BrN3O
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 1h; | 100% |
4-hydroxycyclohexanone
tert-butyldimethylsilyl chloride
4-(tert-butyldimethylsilyloxy)cyclohexanone
Conditions | Yield |
---|---|
With 1H-imidazole | 99% |
With 1H-imidazole In dichloromethane for 1h; Ambient temperature; | 98% |
With 1H-imidazole 1.) CH2Cl2, 0 deg C, 15 min, 2.) CH2Cl2, RT, overnight; Yield given. Multistep reaction; |
4-hydroxycyclohexanone
methanesulfonyl chloride
4-oxocyclohexyl methanesulfonate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 20℃; for 16h; Inert atmosphere; | 98% |
With triethylamine In dichloromethane at 0℃; for 0.5h; Yield given; | |
With triethylamine In dichloromethane at 0 - 20℃; |
Conditions | Yield |
---|---|
Stage #1: 3-Phenylpropenol With 1,1'-bis-(diphenylphosphino)ferrocene; bis(η3-allyl-μ-chloropalladium(II)) In methanol at 20℃; for 0.166667h; Inert atmosphere; Stage #2: 4-hydroxycyclohexanone With pyrrolidine In methanol for 12h; Inert atmosphere; | 98% |
4-hydroxycyclohexanone
4-Phenylbutyric acid
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; Steglich Esterification; | 97% |
4-hydroxycyclohexanone
(S,S)-hydrobenzoin
(2S,3S)-2,3-Diphenyl-1,4-dioxa-spiro[4.5]decan-8-ol
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene for 3.5h; Heating; | 96% |
4-hydroxycyclohexanone
Cyclopropylamine
4-(cyclopropylamino)cyclohexanol
Conditions | Yield |
---|---|
Stage #1: 4-hydroxycyclohexanone; Cyclopropylamine With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 20℃; for 13h; Stage #2: With sodium hydroxide In water; 1,2-dichloro-ethane | 96% |
Conditions | Yield |
---|---|
Stage #1: methanol; 4-hydroxycyclohexanone With trimethyl orthoformate; toluene-4-sulfonic acid at 20℃; for 0.166667h; Heating / reflux; Stage #2: With sodium hydrogencarbonate In methanol; water at 0℃; pH=7; | 95% |
at 0 - 20℃; for 1h; Inert atmosphere; Molecular sieve; | 10.95 g |
3,4-dihydro-2H-pyran
4-hydroxycyclohexanone
4-(tetrahydro-2H-pyran-2-yloxy)cyclohexanone
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In dichloromethane for 1.5h; ice-bath; | 94% |
With trichlorophosphate | |
With toluene-4-sulfonic acid for 0.666667h; Ambient temperature; |
chloro-trimethyl-silane
4-hydroxycyclohexanone
1,4-bis(trimethylsilyloxy)cyclohex-1-ene
Conditions | Yield |
---|---|
With triethylamine; sodium iodide In acetonitrile at -30 - 20℃; Inert atmosphere; | 92% |
With triethylamine In N,N-dimethyl-formamide for 4.5h; Heating; | 68% |
Stage #1: 4-hydroxycyclohexanone With lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 1h; Metallation; Stage #2: chloro-trimethyl-silane In tetrahydrofuran; hexane at -78 - 20℃; for 1h; silylation; |
allyl propyl ether
4-hydroxycyclohexanone
2-allyl-4-hydroxycyclohexanone
Conditions | Yield |
---|---|
With pyrrolidine; 1,1'-bis-(diphenylphosphino)ferrocene; bis(η3-allyl-μ-chloropalladium(II)) In methanol at 20℃; for 12h; Inert atmosphere; regioselective reaction; | 92% |
Conditions | Yield |
---|---|
With pyridine at 0 - 20℃; for 12.5h; Inert atmosphere; | 91% |
4-hydroxycyclohexanone
chloroacetyl chloride
4-oxo-cyclohexyl chloroacetate
Conditions | Yield |
---|---|
With pyridine at 0 - 20℃; for 12.5h; Inert atmosphere; | 91% |
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 4h; | 90.6% |
4-hydroxycyclohexanone
2,2-Dimethyl-1,3-propanediol
3,3-dimethyl-1,5-dioxaspiro<5.5>undecan-9-ol
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene for 4.6h; Heating; | 90% |
4-hydroxycyclohexanone
4-methoxy-benzoyl chloride
Conditions | Yield |
---|---|
With triethylamine for 24h; Ambient temperature; | 90% |
With pyridine In dichloromethane at 45℃; for 4h; Inert atmosphere; Schlenk technique; |
Conditions | Yield |
---|---|
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃; Borch Reduction; Inert atmosphere; | 90% |
4-hydroxycyclohexanone
Trichloroacetyl chloride
4-oxo-cyclohexyl trichloroacetate
Conditions | Yield |
---|---|
With pyridine at 0 - 20℃; for 12.5h; Inert atmosphere; | 89% |
4-hydroxycyclohexanone
orthoformic acid triethyl ester
4,4-diethoxycyclohexanone
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In ethanol at 20℃; | 89% |
4-hydroxycyclohexanone
benzaldehyde
Conditions | Yield |
---|---|
With potassium hydroxide In methanol; water at 20℃; Claisen-Schmidt Condensation; | 88% |
4-hydroxycyclohexanone
1,4-Cyclohexanedione
Conditions | Yield |
---|---|
With pyridinium chlorochromate In dichloromethane for 2h; Ambient temperature; | 87% |
tribromoacetyl chloride
4-hydroxycyclohexanone
4-oxo-cyclohexyl tribromoacetate
Conditions | Yield |
---|---|
With pyridine at 0 - 20℃; for 12.5h; Inert atmosphere; | 87% |
Conditions | Yield |
---|---|
With pyridine at 0 - 20℃; for 12.5h; Inert atmosphere; | 87% |
(E)-3-phenylpropenal
4-hydroxycyclohexanone
Conditions | Yield |
---|---|
With potassium hydroxide In methanol; water at 20℃; Claisen-Schmidt Condensation; | 87% |
The 4-Hydroxycyclohexanone with CAS registry number of 13482-22-9 is also known as Cyclohexanone, 4-hydroxy-. The IUPAC name is 4-Hydroxycyclohexan-1-one. It belongs to product categories of Pharmacetical; Miscellaneous. In addition, the formula is C6H10O2 and the molecular weight is 114.14.
Physical properties about 4-Hydroxycyclohexanone are: (1)ACD/BCF (pH 5.5): 1; (2)ACD/BCF (pH 7.4): 1; (3)ACD/KOC (pH 5.5): 5.173; (4)ACD/KOC (pH 7.4): 5.173; (5)#H bond acceptors: 2; (6)#H bond donors: 1; (7)#Freely Rotating Bonds: 1; (8)Polar Surface Area: 37.3Å2; (9)Index of Refraction: 1.5; (10)Molar Refractivity: 29.391 cm3; (11)Molar Volume: 99.939 cm3; (12)Polarizability: 11.652×10-24cm3; (13)Surface Tension: 46.399 dyne/cm; (14)Density: 1.142 g/cm3; (15)Flash Point: 91.392 °C; (16)Enthalpy of Vaporization: 53.809 kJ/mol; (17)Boiling Point: 226.28 °C at 760 mmHg; (18)Vapour Pressure: 0.016 mmHg at 25 °C.
When you are using this chemical, please be cautious about it. As a chemical, it is irritating to eyes, respiratory system and skin. During using it, wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
1. SMILES: C1CC(=O)CCC1OCopyCopied
2. InChI: InChI=1/C6H10O2/c7-5-1-2-6(8)4-3-5/h5,7H,1-4H2 CopyCopied
3. InChIKey: BXBJZYXQHHPVGO-UHFFFAOYAN
4. Std. InChI: InChI=1S/C6H10O2/c7-5-1-2-6(8)4-3-5/h5,7H,1-4H2 CopyCopied
5. Std. InChIKey: BXBJZYXQHHPVGO-UHFFFAOYSA-N
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