Conditions | Yield |
---|---|
With [NiII(tetrakis(2,6-di(n-butoxy)phenyl)porphyrinato)]; 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 0.166667h; Inert atmosphere; Schlenk technique; | 100% |
With dihydrogen peroxide; teterabutylammonium In acetonitrile at 31.85℃; for 3h; | 99% |
With tert.-butylhydroperoxide In acetonitrile at 65 - 68℃; for 9h; | 99% |
Conditions | Yield |
---|---|
With sodium tungstate (VI) dihydrate; phosphoric acid; dihydrogen peroxide In 5,5-dimethyl-1,3-cyclohexadiene; water at 60℃; for 2h; pH=1.6; Kinetics; Reagent/catalyst; Solvent; | A 5.9% B 93.4% |
Cyclopentene oxide
Conditions | Yield |
---|---|
decompn. at 200°C for 0.5 h; | 86% |
4-cyano-N,N-dimethylaniline-N-oxide
cyclopentene
A
Cyclopentene oxide
B
4-cyano-N-methylaniline
C
4-cyano-N,N-dimethylaniline
Conditions | Yield |
---|---|
With 1H-imidazole; [Mn(2,3,7,8,12,13,17,18-octamethyl-5,10,15,20-tetraphenylporphyrin)Cl] In dichloromethane at 25℃; Product distribution; with various alkene concentrations; | A 80% B 20% C 79% |
Cyclopentene oxide
Conditions | Yield |
---|---|
decompn. at 100°C for 0.5 h; | 73% |
decompn. at 100°C for 0.5 h; | 73% |
Conditions | Yield |
---|---|
With sodium hydroxide; p-toluenesulfonyl chloride; benzyltriethylammonium bromide In dichloromethane at 25℃; for 0.166667h; | 71% |
tert.-butylhydroperoxide
cyclopentene
A
Cyclopentene oxide
B
tert. Butyl-2-cyclopenten-1-yl-peroxid
Conditions | Yield |
---|---|
With palladium diacetate; potassium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In dichloromethane at 0℃; for 48h; | A n/a B 63% |
cyclopentene
A
Cyclopentene oxide
B
cyclopentane-1,2-diol
C
Glutaraldehyde
Conditions | Yield |
---|---|
With dihydrogen peroxide; H3PMo10W2O40 at 35℃; for 3h; | A 0.8% B 13.9% C 60.6% |
With dihydrogen peroxide; H3PMo10W2O40 at 35℃; for 3h; Product distribution; various molybdenum compounds as catalysts; | A 0.8% B 13.9% C 60.6% |
cyclopentene
A
Cyclopentene oxide
B
cyclopent-2-enol
C
cyclopent-2-enone
Conditions | Yield |
---|---|
With 6C16H36N(1+)*2Zn(2+)*4Na(1+)*[Bi2Zn2(ZnW9O34)2](14-); urea hydrogen peroxide adduct In acetonitrile at 70℃; for 24h; Ene Reaction; | A 10% B 32% C 58% |
With oxygen In chlorobenzene at 50℃; Mechanism; Product distribution; catalysts Co(acac)3 and MoO2(acac)2; | A 10.4 % Chromat. B n/a C n/a |
With air; iron 5,10,15,20-tetrakis-(2',6'-dichlorophenyl)porphyrinate; iodosylbenzene In dichloromethane for 0.5h; Product distribution; Mechanism; var. cycloalkenes; other porphyrin; var. reaction time; | A 64 % Chromat. B 19 % Chromat. C 1.9 % Chromat. |
Conditions | Yield |
---|---|
With dihydrogen peroxide In acetonitrile at 65 - 68℃; for 9h; | A 39% B 16% |
With sodium hypochlorite In acetonitrile at 65 - 68℃; for 9h; | A 5% B 14% |
With oxygen; isobutyraldehyde at 50℃; for 6h; Catalytic behavior; Reagent/catalyst; | A 89 %Chromat. B 11 %Chromat. |
2-chlorocyclopentane-1-ol
Cyclopentene oxide
Conditions | Yield |
---|---|
With potassium hydroxide | |
With potassium hydroxide; diethyl ether |
Conditions | Yield |
---|---|
With dichloromethane; sodium carbonate |
2-t-butylperoxycyclopentane-1-yl
A
Cyclopentene oxide
B
cyclopentyl t-butyl peroxide
Conditions | Yield |
---|---|
With tri-n-butyl-tin hydride In benzene at 24.9℃; Rate constant; Irradiation; |
4-cyano-N,N-dimethylaniline-N-oxide
cyclopentene
A
Cyclopentene oxide
B
4’-cyano-N-methylformanilide
C
4-cyano-N-methylaniline
D
N,N'-dimethyl-N,N'-bis-(p-cyanophenyl)hydrazine
E
N,N'-bis-(p-cyanophenyl)-N-methylmethylenediamine
F
4-cyano-N,N-dimethylaniline
Conditions | Yield |
---|---|
With (2,3,7,8,12,13,17,18-octamethyl-5,10,15,20-tetraphenylporphinato)iron(III) chloride In dichloromethane at 25℃; Product distribution; |
3-bromo-4,5-dihydro-5-hydroperoxy-4,4-dimethyl-3,5-diphenyl-3H-pyrazole
cyclopentene
A
Cyclopentene oxide
B
3-bromo-4,5-dihydro-5-hydroxy-4,4-dimethyl-3,5-diphenyl-3H-pyrazole
Conditions | Yield |
---|---|
In chloroform-d1 at 34℃; Rate constant; | A 41 % Spectr. B 41 % Spectr. |
Conditions | Yield |
---|---|
With oxygen 1.) 35 deg C, 101.3 kPa; 2.) pyrolysis GLC; Multistep reaction; | |
With Ce0.3Co0.7Fe2O4; dihydrogen peroxide In 1,4-dioxane at 90℃; for 9h; | A 76.7 %Chromat. B 11.6 %Chromat. |
With Ca0.1Co0.9Fe2O4; dihydrogen peroxide In N,N-dimethyl-formamide at 60℃; for 8h; Catalytic behavior; Solvent; Reagent/catalyst; Schlenk technique; |
cyclopentene
A
Cyclopentene oxide
B
cyclopent-1-en-3-yl hydroperoxide
C
2-(Cyclopent-2-enylperoxy)-cyclopentyl-hydroperoxide
Conditions | Yield |
---|---|
With oxygen at 35℃; under 759.8 Torr; | A 14 % Chromat. B n/a C n/a |
With 2,2'-azobis(isobutyronitrile); oxygen at 35℃; under 759.8 Torr; for 145h; Mechanism; Product distribution; quantity mol O2 per mol olefine; | A 14 % Chromat. B n/a C n/a |
With oxygen at 35℃; under 759.8 Torr; | |
With oxygen at 35℃; under 759.8 Torr; Yield given. Yields of byproduct given; |
cyclopentene
A
Cyclopentene oxide
B
cyclopent-2-enol
C
cyclopent-2-enone
D
cyclopentanone
Conditions | Yield |
---|---|
With bis(acetonitrile)chloronitropalladium(II) In dichloromethane at 20℃; for 6h; Product distribution; other cycloalkenes; | A 4 % Chromat. B 27 % Chromat. C 1 % Chromat. D 3 % Chromat. |
A
Cyclopentene oxide
B
cyclopentyl t-butyl peroxide
Conditions | Yield |
---|---|
With tri-n-butyl-tin hydride; trans-di-O-tert-butyl hyponitrite In benzene for 1.5h; Rate constant; |
A
Cyclopentene oxide
B
cyclopentyl t-butyl peroxide
Conditions | Yield |
---|---|
With sodium hydroxide; sodium tetrahydroborate In dichloromethane 1.) 0 deg C, 30 min, 2.) room temperature, 30 min; Yield given. Yields of byproduct given; |
Conditions | Yield |
---|---|
With oxygen at 35℃; regioselectivity of the autooxidation; other cyclic olefins; |
Cyclopentane
A
Cyclopentene oxide
B
ethene
C
cyclopenta-1,3-diene
D
buta-1,3-diene
E
cyclopentene
F
acrolein
Conditions | Yield |
---|---|
With hydrogen; oxygen at 399.9℃; Product distribution; Rate constant; Mechanism; various O2 pressure; other reaction temperature; |
(+/-)-trans-2-iodocyclopentanol
Cyclopentene oxide
(+/-)-(trans-2-hydroxy-cyclopentyl)-trimethyl-ammonium; iodide
Cyclopentene oxide
Conditions | Yield |
---|---|
Erhitzen des Reaktionsprodukts auf 130grad; |
methanol
(+/-)-(trans-2-hydroxy-cyclopentyl)-trimethyl-ammonium; iodide
A
Cyclopentene oxide
trans-cyclopentane-1,2-diol
Conditions | Yield |
---|---|
Erhitzen des Reaktionsprodukts bis auf 190grad; |
3,3-(α-hydroxytetramethylene)diazirine
A
Cyclopentene oxide
B
cyclopent-2-enol
C
cyclopentanone
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 1h; Photolysis; |
A
Cyclopentene oxide
B
cyclopent-2-enol
C
cyclopentanone
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 1h; Photolysis; |
Cyclopentene oxide
aniline
trans-2-(phenylamino)cyclopentanol
Conditions | Yield |
---|---|
With zirconium(IV) chloride at 20℃; for 0.25h; | 100% |
With lithium bromide at 20℃; for 5h; | 100% |
With sulfated zirconia In neat (no solvent) at 20℃; for 0.5h; regioselective reaction; | 98% |
pyrrolidine
Cyclopentene oxide
(+/-)-trans-(1-pyrrolidinyl)cyclopentan-2-ol
Conditions | Yield |
---|---|
bismuth(lll) trifluoromethanesulfonate at 160℃; for 0.25h; microwave irradiation; | 100% |
With triethylaluminum 1.) toluene, CH2Cl2, 25-30 deg C, 30 min, 2.) room temperature; Yield given. Multistep reaction; | |
In water | |
With potassium carbonate | |
In ethanol at 80℃; for 18h; Inert atmosphere; |
Conditions | Yield |
---|---|
In ethanol for 24h; Heating; | 100% |
In ethanol at 95℃; Sealed tube; | 100% |
With triethylaluminum 1.) toluene, CH2Cl2, 25-30 deg C, 30 min, 2.) room temperature; Yield given. Multistep reaction; |
Cyclopentene oxide
(+/-)-trans-2-iodocyclopentanol
Conditions | Yield |
---|---|
With iodine; tiolacetic acid In dichloromethane at 20℃; for 0.333333h; Ring cleavage; | 100% |
With cerium(III) chloride; sodium iodide In acetonitrile at 20℃; for 0.166667h; | 91% |
With cerium(III) chloride; sodium iodide In acetonitrile at 20℃; for 24h; | 89.5% |
With water; iodine; triphenylphosphine In acetonitrile for 0.25h; Ambient temperature; Yield given; | |
With water; lithium iodide |
Cyclopentene oxide
trans-2-aminocyclopentanol
Conditions | Yield |
---|---|
With ammonium hydroxide at 85℃; for 0.5h; microwave irradiation; | 100% |
With ammonium hydroxide In ethanol at 120 - 140℃; for 5h; in steel autoclave; | 71% |
With ammonium hydroxide at 140℃; under 15200 Torr; |
Conditions | Yield |
---|---|
With sodium amalgam; chiral Co(II) In tetrahydrofuran-d8 at 20℃; for 6h; deoxygenation; | 100% |
With triphenylphosphine at 200℃; for 8.5h; | 59% |
With trifluoroacetic acid; selenobenzamide In dichloromethane at 20℃; for 30h; Mechanism; With other reagents are dicussed.; | 85 % Chromat. |
Conditions | Yield |
---|---|
bismuth(lll) trifluoromethanesulfonate at 160℃; for 0.25h; microwave irradiation; | 100% |
Cyclopentene oxide
4-bromo-3-fluorophenol
Conditions | Yield |
---|---|
With sodium carbonate In propyl cyanide at 175℃; for 2h; microwave irradiation; Inert atmosphere; | 100% |
Cyclopentene oxide
C5H12N2O
Conditions | Yield |
---|---|
With hydrazine hydrate In ethanol at 85℃; for 12h; | 100% |
Cyclopentene oxide
Conditions | Yield |
---|---|
With PEG-400; sodium azide at 20℃; for 0.583333h; | 99% |
With 1‑(1‑carboxymethyl)‑3‑methylimidazolium tetrafluoroborate; sodium azide In neat (no solvent) at 60℃; for 0.5h; Reagent/catalyst; Green chemistry; regioselective reaction; | 95% |
With sodium azide; glycerol-tri(3-methylimidazolium) trimesylate In water at 60℃; for 2h; | 94% |
Cyclopentene oxide
chloro-trimethyl-silane
((1R,2R)-2-Chloro-cyclopentyloxy)-trimethyl-silane
Conditions | Yield |
---|---|
In chloroform at 25℃; for 0.25h; | 99% |
Conditions | Yield |
---|---|
Stage #1: hex-1-yne With n-butyllithium; boron trifluoride diethyl etherate In tetrahydrofuran at -78℃; for 0.5h; Stage #2: Cyclopentene oxide In tetrahydrofuran at -78℃; for 4h; | 99% |
Stage #1: hex-1-yne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.333333h; Stage #2: Cyclopentene oxide With boron trifluoride diethyl etherate In tetrahydrofuran; hexane at -78℃; for 1.3h; Yamaguchi-Hirao alkylation; Further stages.; | 62% |
Cyclopentene oxide
thiobenzoic acid
(+/-)-thiobenzoic acid S-(trans-2-hydroxy-cyclopentyl ester)
Conditions | Yield |
---|---|
With aluminum oxide In diethyl ether at 20℃; for 1h; | 99% |
Conditions | Yield |
---|---|
With acetic acid In water at 20℃; for 0.5h; Solvent; Reagent/catalyst; | 99% |
In ethanol Heating; |
Cyclopentene oxide
2-methoxyphenylmagnesium bromide
2-(2-methoxyphenyl)cyclopentanol
Conditions | Yield |
---|---|
Stage #1: 2-methoxyphenylmagnesium bromide With copper(l) iodide In tetrahydrofuran at 20℃; for 0.166667h; Stage #2: Cyclopentene oxide In tetrahydrofuran at 20℃; Stage #3: With water; ammonium chloride In tetrahydrofuran at 20℃; for 0.5h; | 99% |
Conditions | Yield |
---|---|
With iron oxide In neat (no solvent) at 20℃; for 20h; Green chemistry; regioselective reaction; | 99% |
Conditions | Yield |
---|---|
Stage #1: phenylacetylene With n-butyllithium; boron trifluoride diethyl etherate In tetrahydrofuran at -78℃; for 0.5h; Stage #2: Cyclopentene oxide In tetrahydrofuran at -78℃; for 4h; | 99% |
Conditions | Yield |
---|---|
With acetic acid In neat (no solvent) at 20℃; for 1h; regioselective reaction; | 99% |
Cyclopentene oxide
1-bromo-5-dimethoxy-2-vinylbenzene
Conditions | Yield |
---|---|
Stage #1: 1-bromo-5-dimethoxy-2-vinylbenzene With iodine; magnesium for 0.5h; Reflux; Inert atmosphere; Sealed tube; Stage #2: With copper(l) iodide at 0℃; for 0.5h; Inert atmosphere; Stage #3: Cyclopentene oxide In tetrahydrofuran at 0 - 20℃; for 3h; Inert atmosphere; | 99% |
Cyclopentene oxide
(+/-)-trans-2-chlorocyclopentanol
Conditions | Yield |
---|---|
With morpholine; 1,3,5-trichloro-2,4,6-triazine In water at 20℃; for 0.25h; | 98% |
With zirconyl chloride In acetonitrile at 20℃; for 0.333333h; | 98% |
With cerium(III) chloride In acetonitrile for 1h; Heating; | 90% |
With hydrogenchloride at -20 - -10℃; | |
With hydrogenchloride |
Conditions | Yield |
---|---|
With n-butyllithium In hexane; toluene 1.) 60-65 deg C, 1 h, 2.) 110 deg C, 18 h; | 98% |
Conditions | Yield |
---|---|
With copper(l) iodide In tetrahydrofuran | 98% |
86% |
Conditions | Yield |
---|---|
With boron trifluoride diethyl etherate at -78℃; | 98% |
Cyclopentene oxide
trans-2-phenylcyclopentan-1-ol
Conditions | Yield |
---|---|
With (lithium)2(CN)(phenyl)2cuprate In tetrahydrofuran for 10h; Ambient temperature; | 98% |
Conditions | Yield |
---|---|
With water; tetra(n-butyl)ammonium hydrogensulfate at 20 - 45℃; | 98% |
With water at 100℃; for 18h; | 96% |
With carbon tetrabromide at 60℃; for 3.5h; | 85% |
Cyclopentene oxide
(+/-)-trans-2-bromocyclopentanol
Conditions | Yield |
---|---|
With dimethylbromosulphonium bromide In acetonitrile at 20℃; for 0.333333h; | 98% |
With quaternary ammonium bromide; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; water In acetonitrile for 3h; Heating; | 80% |
With triphenylphosphine hydrobromide In dichloromethane at -90℃; for 0.716667h; Ring cleavage; | 76% |
Cyclopentene oxide
(S)-1-phenyl-ethylamine
2-((S)-1-Phenyl-ethylamino)-cyclopentanol
Conditions | Yield |
---|---|
With lithium perchlorate In acetonitrile for 18h; Heating; | 98% |
With lithium perchlorate In acetonitrile for 18h; Heating; |
Cyclopentene oxide
phenylselenyl zinc chloride
trans-1-hydroxy-2-(phenylseleno)cyclopentane
Conditions | Yield |
---|---|
In water at 20℃; for 2h; | 98% |
Cyclopentene oxide
4-methoxyphenyl magnesium bromide
2-(4-methoxyphenyl)cyclopentanol
Conditions | Yield |
---|---|
Stage #1: 4-methoxyphenyl magnesium bromide With copper(l) iodide In tetrahydrofuran; diethyl ether at -78℃; for 0.5h; Stage #2: Cyclopentene oxide In tetrahydrofuran; diethyl ether at -78 - 20℃; | 98% |
Product Name: Cyclopentene oxide (CAS NO.285-67-6)
Molecular Formula: C5H8O
Molecular Weight: 84.12g/mol
Mol File: 285-67-6.mol
EINECS: 206-005-6
Boiling point: 102 °C at 760 mmHg
Storage Temperature: 2-8°C
Flash Point: 10 °C
Density: 1.071 g/cm3
Refractive index: n20/D 1.434(lit.)
Index of Refraction: 1.49
Molar Refractivity: 22.71 cm3
Molar Volume: 78.5 cm3
Surface Tension: 36.9 dyne/cm
Enthalpy of Vaporization: 32.71 kJ/mol
Vapour Pressure: 39.6 mmHg at 25°C
XLogP3-AA: 0.8
H-Bond Donor: 0
H-Bond Acceptor: 1
Structure Descriptors of Cyclopentene oxide (CAS NO.285-67-6):
IUPAC Name: (1R,5S)-6-oxabicyclo[3.1.0]hexane
Canonical SMILES: C1CC2C(C1)O2
Isomeric SMILES: C1C[C@@H]2[C@H](C1)O2
InChI: InChI=1S/C5H8O/c1-2-4-5(3-1)6-4/h4-5H,1-3H2/t4-,5+
InChIKey: GJEZBVHHZQAEDB-SYDPRGILSA-N
Product Categories: Organics
1. | mmo-sat 15 µmol/plate | MUREAV Mutation Research. 90 (1981),67. | ||
2. | mmo-klp 2 mmol/L | MUREAV Mutation Research. 89 (1981),269. | ||
3. | sce-ham:lng 40 mmol/L | MUREAV Mutation Research. 249 (1991),55. |
Reported in EPA TSCA Inventory.
Safety Information of Cyclopentene oxide (CAS NO.285-67-6):
Hazard Codes:F,Xi
Risk Statements:
11: Highly Flammable
36: Irritating to the eyes
37: Irritating to the respiratory system
38: Irritating to the skin
Safety Statements:
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36: Wear suitable protective clothing
37: Wear suitable gloves
39: Wear eye/face protection
Cyclopentene oxide , its CAS NO. is 285-67-6, the synonyms are Cyclopentane, 1,2-epoxy- ; Cyclopentene epoxide ; Epoxycyclopentane ; cis-1,2-Epoxycyclopentane ; 1,2-Epoxycyclopentane ; 6-Oxabicyclo(3.1.0)hexane .
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