cyclopentanone
methyl iodide
A
1-methylcyclopentanol
B
bicyclopentyl-1,1'-diol
Conditions | Yield |
---|---|
With Pr 1.) THF, 20 deg C, 2.) -20 deg C; | A 86% B 2% |
Conditions | Yield |
---|---|
In diethyl ether for 48h; Ambient temperature; | 70% |
Conditions | Yield |
---|---|
With water; Amberlyst 15 In isopropyl alcohol at 55℃; | 39% |
With water; Amberlyst 15 In isopropyl alcohol at 55℃; for 0.8h; Product distribution / selectivity; | 39% |
acetonitrile
A
S-Phenyl benzenethiosulfonate
C
1-methylcyclopentanol
D
S-phenyl benzenethiosulfinate
E
N-(1-methylcyclopentyl)acetamide
F
diphenyldisulfane
Conditions | Yield |
---|---|
With titanium(IV) oxide; silver sulfate In water at 20℃; for 0.5h; Irradiation; | A n/a B 0.8% C 27.3% D n/a E 5.5% F n/a |
Conditions | Yield |
---|---|
With palladium 10% on activated carbon In diethyl ether; toluene at 0℃; Inert atmosphere; | 22% |
With diethyl ether |
methyl magnesium iodide
1-hydroxycyclopentanecarbonitrile
1-methylcyclopentanol
Conditions | Yield |
---|---|
With diethyl ether |
1-methyl-4-nitrosobenzene
1-methyl-cyclopentyl hydroperoxide
A
n-hexan-2-one
B
1-methylcyclopentanol
C
2-oxo-propionic acid
1-chloro-1-methylcyclopentane
A
1-methylcyclopent-1-ene
B
1-methylcyclopentanol
Conditions | Yield |
---|---|
With water In ethanol at 30℃; Rate constant; solvolysis reaction; | |
With calcium hydroxide; water at 35℃; |
1-methyl-cyclopentyl hydroperoxide
A
n-hexan-2-one
B
6-hydroxy-2-hexanone
C
1-methylcyclopentanol
Conditions | Yield |
---|---|
With magnesium Zerlegen der Magnesiumverbindung mit Wasser; | |
With magnesium 1.) ether, 2.) ether, from 0 deg C to reflux, 2 h; Yield given. Multistep reaction; | |
With lithium In tetrahydrofuran at 40 - 65℃; for 3h; Inert atmosphere; |
6-chloro-2-hexanone
1-methylcyclopentanol
Conditions | Yield |
---|---|
With amalgamated magnesium In tetrahydrofuran | |
Multi-step reaction with 2 steps 1: NaI / acetone 2: 21 percent Chromat. / tetrahydrofuran / -100 °C View Scheme | |
Multi-step reaction with 2 steps 1: NaI / acetone 2: 26 percent Chromat. / t-BuLi / diethyl ether / -78 °C / Var.: n-BuLi, THF, -100 deg C View Scheme |
6-Bromo-2-hexanone
1-methylcyclopentanol
Conditions | Yield |
---|---|
With amalgamated magnesium In tetrahydrofuran | |
With CuI*P(n-Bu)3; tributylphosphine; oxonium; naphthalen-1-yl-lithium 1. THF, -78 deg C, 20min; Yield given. Multistep reaction; |
n-butyllithium
1-iodo-5-hexanone
A
1-methylcyclopentanol
B
1-Iodo-5-methyl-nonan-5-ol
Conditions | Yield |
---|---|
In tetrahydrofuran at -100℃; Title compound not separated from byproducts; | A 21 % Chromat. B 35 % Chromat. |
2-(3-Iodo-propyl)-2-methyl-oxirane
A
1-methylcyclopentanol
B
(1-methylcyclobutyl)methanol
Conditions | Yield |
---|---|
With tert.-butyl lithium In diethyl ether; pentane at -78℃; Product distribution; Effect of additive or warming.; | |
With tert.-butyl lithium 1.) Et2O, pentane, -78 deg C, 5 min; 2.) warming; Yield given. Multistep reaction. Yields of byproduct given; |
1-iodo-5-hexanone
tert.-butyl lithium
A
2,2,3-trimethyl-3-heptanol
B
n-hexan-2-one
C
1-methylcyclopentanol
Conditions | Yield |
---|---|
In diethyl ether at -78℃; Title compound not separated from byproducts; | A 21 % Chromat. B 23 % Chromat. C 26 % Chromat. |
1-iodo-5-hexanone
A
2,2,3-trimethyl-3-heptanol
B
n-hexan-2-one
C
1-methylcyclopentanol
Conditions | Yield |
---|---|
With tert.-butyl lithium In diethyl ether at -78℃; Title compound not separated from byproducts; | A 21 % Chromat. B 23 % Chromat. C 26 % Chromat. |
With tert.-butyl lithium In diethyl ether at -78℃; Var.: n-BuLi, THF, -100 deg C; Title compound not separated from byproducts; | A 21 % Chromat. B 23 % Chromat. C 26 % Chromat. |
methylenecyclopentane
A
cyclopent-1-ene-1-methanol
B
1-Methylol-1-hydroxycyclopentan
C
2-methylenecyclopentan-1-ol
D
1-methylcyclopentanol
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride; oxygen 1) 60 grad C; Multistep reaction. Further byproducts given. Title compound not separated from byproducts; |
methyl-cyclopentane
A
2-Methylcyclopentanone
B
3-methyl-cyclopentanone
C
1-methylcyclopentanol
D
2-methylcyclopentanol
E
3-methylcyclopentanol
Conditions | Yield |
---|---|
With 2-Picolinic acid; water; Fe3O(OAc)6Pyr3.5 In pyridine; methanol at 25 - 30℃; Product distribution; 15-20 mA/cm2; in futher solvents; |
methyl-cyclopentane
A
2-Methylcyclopentanone
B
3-methyl-cyclopentanone
C
1-methylcyclopentanol
D
1-methylcyclopentyl acetate
Conditions | Yield |
---|---|
With N,N,N,N-tetraethylammonium tetrafluoroborate; (Fe3O(OAc)6)(C6H5N)3.5 In water; acetic acid; acetone Ambient temperature; 15-20 mA/cm2; Yield given. Further byproducts given. Yields of byproduct given; |
methyl-cyclopentane
A
2-Methylcyclopentanone
B
3-methyl-cyclopentanone
C
1-methylcyclopentanol
D
3-methylcyclopentanol
Conditions | Yield |
---|---|
With 2-Picolinic acid; (Fe3O(OAc)6)(C6H5N)3.5 In pyridine; water at 25 - 30℃; 15-20 mA/cm2; Yield given. Further byproducts given. Yields of byproduct given; |
Conditions | Yield |
---|---|
With water; hydrogen In gas Product distribution; Irradiation; gas-phase reaction of radiolytically formed cyclohexyl cation with water; evidence for cyclohexyl cation existence, structure and isomerisation of the C6H11+ ions; product yield dependence on pressure and composition of the gaseous system; | 100 % Chromat. |
With di(hydroxo)germanium (5,10,15,20-tetraphenylporphyrin) / silica gel composite In water Irradiation; Inert atmosphere; |
2-(3-Bromo-propyl)-2-methyl-oxirane
1-methylcyclopentanol
Conditions | Yield |
---|---|
With copper; triphenylphosphine In tetrahydrofuran | 95 % Chromat. |
With copper(l) iodide; lithium dihydronaphthylide radical; triphenylphosphine In tetrahydrofuran 1) -45 deg C, 5 min, -23 deg C, 3 h, r.t.; | 95 % Chromat. |
cyclohexyl cation
A
1-methylcyclopentanol
B
cyclohexanone
C
cyclohexanol
Conditions | Yield |
---|---|
With water In gas Product distribution; evidence for cyclohexyl cation existence, structure and isomerisation of the C6H11+ ions; product yield dependence on pressure and composition of the gaseous system; | A 23 % Chromat. B 23 % Chromat. C 54 % Chromat. |
dichloromethane
cyclopentanone
A
1-methylcyclopentanol
B
bicyclopentyl-1,1'-diol
Conditions | Yield |
---|---|
With water; lithium; 4,4'-di-tert-butylbiphenyl 1.) THF, -40 deg C, 55 min; Yield given. Multistep reaction. Yields of byproduct given; |
1-methylcyclopentyl acetate
1-methylcyclopentanol
Conditions | Yield |
---|---|
With perchloric acid In 1,4-dioxane at 15 - 45℃; Kinetics; |
4-oxo-nonanal
A
3-octanone
B
n-hexan-3-ol
C
n-hexan-2-ol
D
nonane-1,4-diol
E
n-hexan-2-one
F
1-methylcyclopentanol
Conditions | Yield |
---|---|
In hexane for 960h; Product distribution; Ambient temperature; thermal treatment; | A 8.17 % Chromat. B 0.74 % Chromat. C 0.95 % Chromat. D 5.25 % Chromat. E 1.56 % Chromat. F 0.78 % Chromat. |
1-methylcyclopentanol
6-chloro-2-hexanone
Conditions | Yield |
---|---|
With sodium hydrogencarbonate; iron(II) sulfate In tetrachloromethane Ambient temperature; in the dark; | 100% |
With lead(IV) acetate; lithium chloride at 20 - 35℃; for 4h; Oxidation; oxidative decyclization; mechanical activation; | 51% |
(i) aq. NaOCl, (ii) AgNO3, NaOH, aq. NH3; Multistep reaction; |
1-methylcyclopentanol
chloro-diphenylphosphine
(1-methylcyclopent-1-yloxy)di(phenyl)phosphine
Conditions | Yield |
---|---|
With dmap; triethylamine In tetrahydrofuran at 20℃; for 2h; | 98% |
With dmap; triethylamine In tetrahydrofuran at 20℃; for 2h; | 98% |
With dmap; triethylamine In tetrahydrofuran at 20℃; for 2h; | 95% |
1-methylcyclopentanol
6-Bromo-2-hexanone
Conditions | Yield |
---|---|
With bromine; potassium carbonate In chloroform at 0℃; for 5h; Bromination; retro-Barbier fragmentation; | 97% |
With [bis(acetoxy)iodo]benzene; sodium bromide In acetonitrile at 20℃; for 10h; Inert atmosphere; Irradiation; | 86% |
Stage #1: 1-methylcyclopentanol With potassium carbonate In chloroform at 0℃; for 0.25h; Stage #2: With bromine In chloroform at 0℃; for 2.5h; | 56% |
Conditions | Yield |
---|---|
95% | |
With iodine; oxalic acid | 87% |
With iodine Erhitzen des erhaltenen Gemisches von 1-Methyl-cyclopenten und Methylencyclopentan mit Essigsaeure und wenig Toluol-4-sulfonsaeure; |
Conditions | Yield |
---|---|
Stage #1: 1-methylcyclopentanol; sodium cyanide With sulfuric acid; acetic acid at 20℃; for 22.56h; Ritter Reaction; Stage #2: With sodium hydroxide; water at 0℃; pH=9; | 95% |
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 23℃; for 1h; Inert atmosphere; | 94% |
With dmap; triethylamine In tetrahydrofuran at 0 - 25℃; for 5h; Inert atmosphere; | 84% |
With dmap; triethylamine In tetrahydrofuran |
Conditions | Yield |
---|---|
Stage #1: 1-methylcyclopentanol With [bis(pyridine)iodine]+ tetrafluoroborate; caesium carbonate In dichloromethane at 20℃; for 8h; UV-irradiation; Stage #2: With sulfuric acid In water | 93% |
With [bis(pyridine)iodine]+ tetrafluoroborate; caesium carbonate In dichloromethane at 20℃; for 8h; Irradiation; | 93% |
With [bis(acetoxy)iodo]benzene; sodium iodide In acetonitrile at 20℃; for 10h; Inert atmosphere; Irradiation; | 78% |
With [bis(acetoxy)iodo]benzene; iodine In dichloromethane at 20℃; for 0.0833333h; UV-irradiation; |
t-butoxalyl chloride
1-methylcyclopentanol
Conditions | Yield |
---|---|
With pyridine; dmap In dichloromethane at 0 - 20℃; Inert atmosphere; | 93% |
Conditions | Yield |
---|---|
With cerium(III) chloride; tetrabutyl-ammonium chloride In acetonitrile for 12h; Inert atmosphere; Irradiation; | 84% |
Conditions | Yield |
---|---|
With bismuth(lll) trifluoromethanesulfonate; water Ritter reaction; | 82% |
With 1-methyl-3-(4-sulfonylbutyl)-1H-imidazol-3-ium trifluoromethanesulfonate; acetic acid at 80℃; for 24h; Ritter reaction; Inert atmosphere; Ionic liquid; | 65% |
1-methylcyclopentanol
4-methoxybenzonitrile
N-1-methylcyclopentane-4-methoxy-benzamide
Conditions | Yield |
---|---|
With 1-methyl-3-(4-sulfonylbutyl)-1H-imidazol-3-ium trifluoromethanesulfonate; acetic acid at 70℃; for 12h; Ritter reaction; Inert atmosphere; Ionic liquid; | 82% |
1-methylcyclopentanol
benzoyl triflate
1-methylcyclopentanol benzoate
Conditions | Yield |
---|---|
With pyridine In dichloromethane 1) 30 min, -78 deg C; 2) 1 h, room temperature; | 81% |
With pyridine In dichloromethane 1.) 0 deg C, 30 min, 2.) room temp., 1 h; | 81% |
1-methylcyclopentanol
propiononitrile
N-1-methylcyclopentane-propanamide
Conditions | Yield |
---|---|
With 1-methyl-3-(4-sulfonylbutyl)-1H-imidazol-3-ium trifluoromethanesulfonate; acetic acid at 65℃; for 24h; Ritter reaction; Inert atmosphere; Ionic liquid; | 81% |
Conditions | Yield |
---|---|
With caesium carbonate In acetonitrile at 20℃; for 24h; Inert atmosphere; | 80% |
2-furancarbonitrile
1-methylcyclopentanol
N-1-methylcyclopentane-furanamide
Conditions | Yield |
---|---|
With 1-methyl-3-(4-sulfonylbutyl)-1H-imidazol-3-ium trifluoromethanesulfonate; acetic acid at 80℃; for 12h; Ritter reaction; Inert atmosphere; Ionic liquid; | 78% |
Conditions | Yield |
---|---|
With cyclopentadienyl titanium(IV) trichloride; triethylsilyl chloride; zinc In tetrahydrofuran at 60℃; for 12h; Molecular sieve; Sealed tube; Inert atmosphere; | 77% |
Conditions | Yield |
---|---|
With lead(IV) acetate; ortho-chlorobenzoic acid at 20℃; for 20h; | 76% |
With lead(IV) acetate; ortho-chlorobenzoic acid for 20h; | 76% |
With lead(IV) acetate In acetic acid at 80℃; | 57 % Turnov. |
Conditions | Yield |
---|---|
With sulfuric acid; acetic acid at 0 - 20℃; for 3h; | 74% |
Conditions | Yield |
---|---|
With 1-methyl-3-(4-sulfonylbutyl)-1H-imidazol-3-ium trifluoromethanesulfonate; acetic acid at 40℃; for 24h; Ritter reaction; Inert atmosphere; Ionic liquid; | 73% |
With sulfuric acid |
1-methylcyclopentanol
acetic anhydride
A
1-methylcyclopentyl acetate
B
1'-methylcyclopentyl 3-oxobutanoate
C
dimethylglyoxal
Conditions | Yield |
---|---|
With cobalt(II) chloride In acetonitrile at 70℃; for 10h; | A 73% B 17% C n/a |
trimethylsilylazide
1-methylcyclopentanol
1-amino-1-methylcyclopentane hydrochloride
Conditions | Yield |
---|---|
Stage #1: trimethylsilylazide; 1-methylcyclopentanol With boron trifluoride diethyl etherate In benzene for 24h; Stage #2: With hydrogen; palladium 10% on activated carbon In methanol at 20℃; under 2327.23 Torr; for 1.5h; Stage #3: With hydrogenchloride In water | 71% |
Conditions | Yield |
---|---|
With C7H10N2*C8HF15O2 at 60℃; for 24h; neat (no solvent); | 70% |
With zinc(II) chloride |
Conditions | Yield |
---|---|
With pyridine; lead(IV) acetate; lithium chloride In benzene at 80℃; for 5h; | A 15% B 70% |
Conditions | Yield |
---|---|
With pyridine; lead(IV) acetate; sodium bromide In benzene at 80℃; for 3h; | A 15% B 70% |
With pyridine; lead(IV) acetate; lithium bromide In benzene at 80℃; for 3h; Product distribution; other MBr; | A n/a B 65 % Turnov. |
1-methylcyclopentanol
2,2,6-trimethyl-4H-1,3-dioxin-4-one
1'-methylcyclopentyl 3-oxobutanoate
Conditions | Yield |
---|---|
In xylene for 0.5h; Heating; | 70% |
Conditions | Yield |
---|---|
With lead(IV) acetate; ortho-chlorobenzoic acid for 20h; | 70% |
1-methylcyclopentanol
2-Methylpropionic anhydride
1-methylcyclopentyl isobutyrate
Conditions | Yield |
---|---|
With C7H10N2*C8HF15O2 at 60℃; for 24h; neat (no solvent); | 68% |
Conditions | Yield |
---|---|
In hexane at -40 - 20℃; for 3h; Inert atmosphere; Schlenk technique; | 68% |
This chemical is called Cyclopentanol, 1-methyl-, and its systematic name is 1-Methylcyclopentanol. With the molecular formula of C6H12O, its product categories are Medical Intermediates; Alcohols; C2 to C6; Oxygen Compounds. The CAS registry number of this chemical is 1462-03-9. In addition, this chemical should be sealed in the cool and dry place, away from oxides.
Other characteristics of the Cyclopentanol, 1-methyl- can be summarised as followings: (1)ACD/LogP: 1.32; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.32; (4)ACD/LogD (pH 7.4): 1.32; (5)ACD/BCF (pH 5.5): 5.9; (6)ACD/BCF (pH 7.4): 5.9; (7)ACD/KOC (pH 5.5): 124.06; (8)ACD/KOC (pH 7.4): 124.06; (9)#H bond acceptors: 1; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 9.23 Å2; (13)Index of Refraction: 1.473; (14)Molar Refractivity: 29.26 cm3; (15)Molar Volume: 104.1 cm3; (16)Polarizability: 11.6×10-24cm3; (17)Surface Tension: 33.5 dyne/cm; (18)Density: 0.961 g/cm3; (19)Flash Point: 40.6 °C; (20)Enthalpy of Vaporization: 43.63 kJ/mol; (21)Boiling Point: 137.1 °C at 760 mmHg; (22)Vapour Pressure: 3.03 mmHg at 25°C.
Production method of this chemical: The Cyclopentanol, 1-methyl- could be obtained by the reactants of cyclopentanone and Triisopropoxy-methyl-titan. This reaction needs the solvent of diethyl ether. The yield is 70 %. In addition, this reaction should be taken for 48 hours at the ambienet temperature.
Uses of this chemical: The Cyclopentanol, 1-methyl- could react with benzoyl trifluoromethanesulfonate, and obtain the 1-methylcyclopentanol benzoate. This reaction needs the reagent of pyridine, and the solvent of CH2Cl2. The yield is 81 %.
When you are using this chemical, please be cautious about it as the following: This chemical is highly flammable or harmful if swallowed. It has risk of serious damage to the eyes. You should wear suitable protective clothing if you use it. In case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
1.SMILES: OC1(C)CCCC1
2.InChI: InChI=1/C6H12O/c1-6(7)4-2-3-5-6/h7H,2-5H2,1H3
3.InChIKey: CAKWRXVKWGUISE-UHFFFAOYAG
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