1-<2-trimethylsilyl)ethyl>cyclohexanol
vinylcyclohexane
Conditions | Yield |
---|---|
With borontrifluoride acetic acid In dichloromethane at 25℃; for 0.0833333h; | 95% |
Conditions | Yield |
---|---|
With hydrogen In hexane at 20℃; under 760.051 Torr; for 14h; | 92% |
With silver(I) tetrakis(3,5-bis(trifluoromethyl)phenyl)borate; C19H13I2N3O2Ru; hydrogen In isopropyl alcohol at 80℃; under 3750.38 Torr; for 1h; Autoclave; Schlenk technique; chemoselective reaction; | 89% |
With hydrogen In toluene at 20℃; under 38002.6 Torr; for 12h; Autoclave; chemoselective reaction; | 72% |
Conditions | Yield |
---|---|
With trifluoroacetic anhydride | 76% |
Methylenetriphenylphosphorane
cyclohexanecarbaldehyde
A
vinylcyclohexane
B
Triphenylphosphine oxide
Conditions | Yield |
---|---|
In tetrahydrofuran 1) 2 h, reflux, 2) 12 h, r.t.; | A 68% B n/a |
Conditions | Yield |
---|---|
In 1,4-dioxane at 120℃; for 15h; Schlenk technique; Inert atmosphere; | 65% |
methyl trifluoromethanesulfonate
cyclohexanecarbaldehyde
vinylcyclohexane
Conditions | Yield |
---|---|
With scandium tris(trifluoromethanesulfonate) In acetonitrile Wittig Olefination; Inert atmosphere; Glovebox; Electrochemical reaction; | 57% |
Conditions | Yield |
---|---|
With sodium tetrahydroborate; hydrogen; nickel dichloride In isopropyl alcohol at 60 - 70℃; for 12h; | A 56% B 14% C 28% |
Conditions | Yield |
---|---|
Stage #1: vinylidenecyclohexane With triethylsilane; indium(III) chloride; triethyl borane In hexane; acetonitrile at 20℃; for 2h; Inert atmosphere; Stage #2: With hydrogenchloride; water In hexane; acetonitrile regioselective reaction; | A 10% B 32% |
With water; diisobutylaluminium hydride 1.) hexane, 15 h, 25°C; 2.) 0°C; Multistep reaction; |
Conditions | Yield |
---|---|
In dimethyl sulfoxide Irradiation (UV/VIS); mixt. of substrate and mercurial is irradiated in nitrogen-purged solvent in Pyrex tube with 350-nm Rayonet photoreactor for 24 h; mixt. is poured into water, extd., extract is washed twice with aq. sodium thiosulfate, dried over anhyd. Na2SO4, concd.; (1)H-NMR; | 8% |
styrene
A
vinylcyclohexane
B
ethyl-cyclohexane
C
ethylbenzene
Conditions | Yield |
---|---|
With hydrogen; (η3-C3H5)Co[P(OMe)3]3 for 20.5h; Ambient temperature; | A 2.8% B 0.3% C 1.5% |
cyclohexyl ethyl acetate
vinylcyclohexane
Conditions | Yield |
---|---|
at 480℃; |
1-cyclohexylethan-1-yl acetate
A
vinylcyclohexane
B
ethylidenecyclohexane
Conditions | Yield |
---|---|
at 450℃; |
(2-iodoethyl)cyclohexane
vinylcyclohexane
Conditions | Yield |
---|---|
With quinoline |
dithiocarbonic acid O-(1-cyclohexyl-ethyl ester)-S-methyl ester
A
vinylcyclohexane
B
ethylidenecyclohexane
Conditions | Yield |
---|---|
at 250℃; |
Conditions | Yield |
---|---|
With 4,4'-di(tert-butyl)-[1,1-biphenyl]yllithium 1) THF, -78 deg C, 5 min 2) MeOH, -78 deg C; Multistep reaction; |
Conditions | Yield |
---|---|
19 % Chromat. |
Conditions | Yield |
---|---|
With bis(cyclopentadienyl)titanium dichloride; sodium tetrahydroborate; 18-crown-6 ether; dihydrogen peroxide; sodium methylate 1.) THF, 65 deg C, 3 h, 2.) CH3OH, 0.5 h; Yield given. Multistep reaction. Yields of byproduct given; |
ethyl-cyclohexane
A
vinylcyclohexane
B
1-ethylcyclohexene
C
ethylidenecyclohexane
D
4-ethylcyclohexene
E
3-ethyl-1-cyclohexene
Conditions | Yield |
---|---|
trans-carbonylchlorobis(trimethylphosphine)rhodium under 50 Torr; for 72h; Mechanism; Irradiation; |
(E)-cyclooctene
A
(Z)-Cyclooctene
B
vinylcyclohexane
C
1,7-Octadiene
Conditions | Yield |
---|---|
at 512℃; Rate constant; further temperatures; |
Conditions | Yield |
---|---|
With η5-C9H11Fe(CO)2(isobutylene)+BF-; hydrogen; sodium iodide; palladium on activated charcoal Multistep reaction; |
Di-(cyclohexyl)-n-butylboran
vinyl magnesium bromide
A
1-hexene
B
vinylcyclohexane
Conditions | Yield |
---|---|
With iodine Product distribution; 1.) THF, room temperature, 1 h, 2.) THF, -78 deg C; other trialkylboranes; |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride; aluminium trichloride; lithium 1.) Et2O, 2.) THF; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With pyridine; lead(IV) acetate; copper diacetate In benzene for 4h; Heating; |
Conditions | Yield |
---|---|
at 400℃; Kinetics; Thermodynamic data; var. temp., pressure; ΔH(excit.); |
Conditions | Yield |
---|---|
With dimethyl sulfoxide at 175℃; for 24h; Yield given. Yields of byproduct given; | |
5 % ruthenium on Al2O3; zirconium(IV) oxide at 376 - 398℃; Product distribution / selectivity; |
trans,trans-4'-butyl<1,1'-bicyclohexyl>-4-carbonitrile
A
vinylcyclohexane
D
acetophenone
Conditions | Yield |
---|---|
at 30℃; Product distribution; Irradiation; Norrish II photoreactivity; different solvents, different temperatures; |
(2-cyclohexylidene-ethyl)dimethyl(phenyl)silane
vinylcyclohexane
Conditions | Yield |
---|---|
With trifluoroacetic acid In tetrachloromethane for 20h; Ambient temperature; | 95 % Spectr. |
bicyclo<5.1.0>octan-2-one tosylhydrazone
A
vinylcyclohexane
B
1-octen-7-yne
C
bicyclo<4.2.0>oct-6-ene
Conditions | Yield |
---|---|
With sodium methylate at 160 - 170℃; under 0.5 Torr; | A 10 % Chromat. B 65 % Chromat. C 25 % Chromat. |
With sodium methylate at 160 - 170℃; under 0.5 Torr; Mechanism; Product distribution; | A 10 % Chromat. B 65 % Chromat. C 25 % Chromat. |
exo-7-chloromethylbicyclo<4.1.0>heptane
A
vinylcyclohexane
B
exo-7-methylbicyclo<4.1.0>heptane
Conditions | Yield |
---|---|
With triphenylstannane In pentane at 25℃; for 24h; Irradiation; Yield given. Yields of byproduct given; | |
With triphenylstannane In pentane at 25℃; for 24h; Product distribution; Rate constant; Mechanism; Irradiation; several amount of reagent; |
vinylcyclohexane
Conditions | Yield |
---|---|
With triphenylstannane for 24h; Irradiation; |
vinylcyclohexane
1-cyclohexylethane-1,2-diol
Conditions | Yield |
---|---|
With 4-methylmorpholine N-oxide In water; acetone at 20℃; for 3.5h; Inert atmosphere; | 100% |
Stage #1: vinylcyclohexane With sodium periodate; acetic acid; lithium bromide at 95℃; for 18h; Prevost-Woodward reaction; Stage #2: With potassium carbonate In methanol at 25℃; for 24h; | 85% |
With osmium(VIII) oxide; N-methyl-2-indolinone In water; acetone; acetonitrile Ambient temperature; | 83% |
vinylcyclohexane
Conditions | Yield |
---|---|
With titanium(IV) isopropylate; Pentafluorobenzoic acid; C32H22F10N2O2; dihydrogen peroxide In water; 1,2-dichloro-ethane at 20℃; for 45h; Inert atmosphere; enantioselective reaction; | 100% |
Conditions | Yield |
---|---|
With peracetic acid; C80H84Mn2N8O4*4ClO4(1-) In acetonitrile at 0℃; for 0.5h; | 99% |
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 0 - 20℃; for 18h; | 97% |
With bis-trimethylsilanyl peroxide; rhenium(VII) oxide In dichloromethane for 7h; | 95% |
Conditions | Yield |
---|---|
With N-bromophthalimide; 4-methylmorpholine N-oxide; sodium sulfate In dichloromethane at 20℃; for 22h; diastereoselective reaction; | 99% |
With N-Bromosuccinimide; 5,6-difluoro-2-(1-phenylethyl)benzo[d][1,2]selenazol-3(2H)-one In dichloromethane at 20℃; for 10h; | 68% |
Conditions | Yield |
---|---|
With 2,2-dimethoxy-2-phenylacetophenone In neat (no solvent) for 0.5h; Solvent; UV-irradiation; | 99% |
Conditions | Yield |
---|---|
bis(cyclopentadienyl)titanium dichloride; lithium aluminium tetrahydride at 180℃; for 2h; | 98% |
With sodium azide on γ-alumina at 20℃; | |
With [(dppb)Pt(C6F5)(H2O)]OTf In chloroform at 50℃; for 24h; | 97 %Chromat. |
vinylcyclohexane
Conditions | Yield |
---|---|
With carbonyl bis(hydrido)tris(triphenylphosphine)ruthenium(II) In toluene at 135℃; for 12h; | 98% |
Conditions | Yield |
---|---|
With 2,2-dimethoxy-2-phenylacetophenone In water for 2h; Solvent; UV-irradiation; Green chemistry; | 98% |
vinylcyclohexane
sodium benzenesulfonate
((2-cyclohexylethyl)sulfonyl)benzene
Conditions | Yield |
---|---|
With [Ir(dF(CF3)ppy)2(dtbbpy)]PF6; water; acetic acid In dichloromethane at 20℃; for 10h; Inert atmosphere; Irradiation; regioselective reaction; | 98% |
vinylcyclohexane
(E)-1-phenyl-N-(1-phenylethylidene)methanamine
Conditions | Yield |
---|---|
Stage #1: vinylcyclohexane; (E)-1-phenyl-N-(1-phenylethylidene)methanamine With [RhCl(Ph3P)2] for 0.25h; microwave irradiation; Stage #2: Acid hydrolysis; | 97% |
vinylcyclohexane
4-methoxy-phenol
4-methoxy-2-(1-cyclohexylethyl)phenol
Conditions | Yield |
---|---|
With decacarbonyldirhenium(0) In toluene at 150℃; for 24h; Inert atmosphere; Sealed tube; regioselective reaction; | 97% |
vinylcyclohexane
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane
Conditions | Yield |
---|---|
With (iPrPNN)CoCl2; sodium triethylborohydride In tetrahydrofuran; toluene at 25℃; for 0.25h; Inert atmosphere; Glovebox; Schlenk technique; chemoselective reaction; | 97% |
Stage #1: vinylcyclohexane; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane With 6-di-tert-butylphosphinomethyl-2,2'-bipyridine In tetrahydrofuran for 0.0166667h; Inert atmosphere; Glovebox; Schlenk technique; Stage #2: With sodium triethylborohydride In tetrahydrofuran at 25℃; for 0.5h; Inert atmosphere; Glovebox; Schlenk technique; | 93% |
With silver hexafluoroantimonate at 60℃; for 24h; Schlenk technique; Glovebox; Inert atmosphere; | 92% |
Conditions | Yield |
---|---|
With 2,2-dimethoxy-2-phenylacetophenone In N,N-dimethyl-formamide for 2h; Solvent; UV-irradiation; Green chemistry; | 97% |
Conditions | Yield |
---|---|
With diethylzinc In hexane; acetonitrile at -20℃; for 16h; Schlenk technique; Inert atmosphere; | 97% |
With potassium carbonate In acetone at 20℃; for 16h; Schlenk technique; Inert atmosphere; Irradiation; Green chemistry; | 96% |
With potassium carbonate In acetone at 20℃; for 16h; Irradiation; | 96% |
Conditions | Yield |
---|---|
With (dppf)Ni(o-tol)Cl; sodium t-butanolate In Hexafluorobenzene at 50℃; for 16h; Inert atmosphere; Schlenk technique; Sealed tube; | 97% |
vinylcyclohexane
(R)-1-cyclohexylethane-1,2-diol
Conditions | Yield |
---|---|
With methanesulfonamide; AD-mix β; water In ethanol at 4℃; for 24h; Sharpless Dihydroxylation; | 96% |
Stage #1: vinylcyclohexane With 2,2'-bis(1,3,2-benzodioxaborole); (bicyclo[2.2.1]hepta-2,5-diene)-(2,4-pentanedionato)rhodium (I); (S)-1-(2-diphenylphosphino-1-naphthyl)isoquinoline In tetrahydrofuran at 20℃; for 6h; Stage #2: With sodium hydroxide; dihydrogen peroxide Product distribution / selectivity; | 81% |
Stage #1: vinylcyclohexane With 1,8-diazabicyclo[5.4.0]undec-7-ene; (2R,3S,4R)-2-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-3,4-diol; 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane In tetrahydrofuran at 20℃; for 48h; Inert atmosphere; Sealed tube; Stage #2: With water; dihydrogen peroxide; sodium hydroxide at 0 - 20℃; for 4h; Inert atmosphere; Sealed tube; enantioselective reaction; | 68% |
vinylcyclohexane
2-pyridylmethyl formate
Conditions | Yield |
---|---|
With tetra-(n-butyl)ammonium iodide; dodecacarbonyl-triangulo-triruthenium In N,N-dimethyl-formamide at 70℃; for 12h; | 96% |
With dodecacarbonyl-triangulo-triruthenium In N,N-dimethyl-formamide at 135℃; for 12h; | 87% |
With 1,3-bis(1-adamantyl)benzimidazoliumchloride, 1,3-dicyclohexylbenzimidazolium chloride; ruthenium(II) (norbanadiene)Cl2; potassium tert-butylate In tetrahydrofuran at 90℃; for 12h; Reagent/catalyst; Concentration; regioselective reaction; | 87% |
vinylcyclohexane
Trichloroacetyl chloride
2,2-dichloro-3-(cyclohexyl)cyclobutanone
Conditions | Yield |
---|---|
With copper; zinc; trichlorophosphate In diethyl ether at 40℃; for 2h; | 96% |
With zinc/copper couple; trichlorophosphate In diethyl ether Reflux; |
vinylcyclohexane
6-methyl-2-vinyl-1,3,6,2-dioxazaborocane-4,8-dione
Conditions | Yield |
---|---|
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 40℃; for 24h; Inert atmosphere; stereoselective reaction; | 96% |
Conditions | Yield |
---|---|
With Fe(PMe3)4 at 70℃; for 20h; Inert atmosphere; regioselective reaction; | 96% |
vinylcyclohexane
[1-chloro-2-(pentafluoro-λ6-sulfanyl)ethyl]cyclohexane
Conditions | Yield |
---|---|
Stage #1: vinylcyclohexane With pentafluorosulfanyl chloride In dichloromethane at -40℃; Stage #2: With triethyl borane In hexane; dichloromethane at -40 - 20℃; Stage #3: With water; sodium hydrogencarbonate In hexane; dichloromethane | 95% |
[2,2]bipyridinyl
vinylcyclohexane
3,3'-bis(2-cyclohexylethyl)-2,2'-bipyridine
Conditions | Yield |
---|---|
With rhodium(III) acetylacetonate; 1,3-bis(mesityl)imidazolium chloride; sodium t-butanolate In toluene at 130℃; for 2h; regioselective reaction; | 95% |
vinylcyclohexane
1-iodo-2,2,3,3,4,4,5,5,5-nonafluorobutane
(3,3,4,4,5,5,6,6,6-nonafluoro-1-iodohexyl)cyclohexane
Conditions | Yield |
---|---|
With tri-tert-butyl phosphine; tris(pentafluorophenyl)borate In dichloromethane at 20℃; for 12h; regioselective reaction; | 95% |
With sodium dithionite; C8ClF16O4S(1-)*C8H20N(1+); sodium hydrogencarbonate In water at 20℃; for 12h; | 90% |
With tri-tert-butyl phosphine In dichloromethane at 30℃; for 1h; Inert atmosphere; Irradiation; Sealed tube; | 87% |
With potassium carbonate In acetone at 20℃; for 16h; Schlenk technique; Inert atmosphere; Irradiation; Green chemistry; | 79% |
With tri-tert-butyl phosphine; tris(pentafluorophenyl)borate In dichloromethane at 20℃; for 24h; Catalytic behavior; Reagent/catalyst; Solvent; Sealed tube; |
Conditions | Yield |
---|---|
With sodium methylate In tetrahydrofuran Heating; | 95% |
With [(2-Ph2PC6H4)2PhSiCo(H)(Cl)(PMe3)] In neat (no solvent) at 70℃; for 30h; Reagent/catalyst; Temperature; Schlenk technique; Inert atmosphere; regioselective reaction; | 95% |
With (1,3-diadamantylimidazol-2-ylidene)(PPh3)CoCl In toluene at 70℃; for 30h; | 89% |
vinylcyclohexane
1,2-dibromo-1-cyclohexylethane
Conditions | Yield |
---|---|
With bromine In chloroform at 0 - 20℃; for 1h; Inert atmosphere; | 94% |
With bromine | |
With bromine In tetrachloromethane | |
With bromine In dichloromethane at 0 - 5℃; | |
With urea hydrogen peroxide adduct; trifluoroacetic acid; lithium bromide at 100℃; for 1h; |
Conditions | Yield |
---|---|
With bis(1,5-cyclooctadiene)nickel (0); tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; triethylamine; 1,3-bis-(2,6-diisopropylphenyl)-imidazol-2-ylidene In acetone at 35℃; for 48h; Heck Reaction; Inert atmosphere; Irradiation; | 94% |
vinylcyclohexane
Conditions | Yield |
---|---|
With C47H47N2O2Sc In benzene-d6 at 75℃; Schlenk technique; Sealed tube; enantioselective reaction; | 94% |
vinylcyclohexane
N-(2-methylbenzoyl)-8-aminoquinoline
Conditions | Yield |
---|---|
With ortho-methylbenzoic acid; di-μ-acetato-bis(η4-1,5-cyclooctadiene)dirhodium(I) In toluene at 160℃; for 12h; Sealed tube; | 94% |
Conditions | Yield |
---|---|
With pyridine; Eosin Y; 1,3-dioxoisoindolin-2-yl 3,3-dimethylbutanoate at 23℃; for 14h; Inert atmosphere; Sealed tube; Irradiation; | 93% |
With dibenzoyl peroxide (heating); |
The CAS register number of Vinylcyclohexane is 695-12-5. It also can be called as Cyclohexane, vinyl- and the IUPAC name about this chemical is ethenylcyclohexane. The molecular formula about this chemical is C8H14 and the molecular weight is 110.20. Classification code about this chemical is Reproductive Effect. This chemical is flammable. When you are using it, please keep away from sources of ignition.
Physical properties about Vinylcyclohexane are: (1)ACD/LogP: 3.90; (2)ACD/LogD (pH 5.5): 3.9; (3)ACD/LogD (pH 7.4): 3.9; (4)ACD/BCF (pH 5.5): 541.15; (5)ACD/BCF (pH 7.4): 541.15; (6)ACD/KOC (pH 5.5): 3148.54; (7)ACD/KOC (pH 7.4): 3148.54 ; (8)#Freely Rotating Bonds: 1; (9)Index of Refraction: 1.515; (10)Molar Refractivity: 38.45 cm3; (11)Molar Volume: 127.3 cm3; (12)Polarizability: 15.24x10-24cm3; (13)Surface Tension: 28.8 dyne/cm; (14)Flash Point: 21.1 °C; (15)Enthalpy of Vaporization: 34.96 kJ/mol; (16)Boiling Point: 126.9 °C at 760 mmHg; (17)Vapour Pressure: 13.8 mmHg at 25°C.
Preparation: this chemical can be prepared by 1-(2-trimethylsilanyl-ethyl)-cyclohexanol. This reaction will need reagent BF3*AcOH and solvent CH2Cl2. The reaction time is 5 min with reaction temperature of 25 °C. The yield is about 95%.
Uses of Vinylcyclohexane: it can be used to produce 1-cyclohexyl-ethanone at temperature of 60 ℃. This reaction will need reagent PdCl(NO2)(CH3CN)2 and solvent benzene.
You can still convert the following datas into molecular structure:
(1)SMILES: C=C\C1CCCCC1
(2)InChI: InChI=1/C8H14/c1-2-8-6-4-3-5-7-8/h2,8H,1,3-7H2
(3)InChIKey: LDLDYFCCDKENPD-UHFFFAOYAK
(4)Std. InChI: InChI=1S/C8H14/c1-2-8-6-4-3-5-7-8/h2,8H,1,3-7H2
(5)Std. InChIKey: LDLDYFCCDKENPD-UHFFFAOYSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LC50 | inhalation | 27gm/m3/2H (27000mg/m3) | "Prehled Prumyslove Toxikologie; Organicke Latky," Marhold, J., Prague, Czechoslovakia, Avicenum, 1986Vol. -, Pg. 22, 1986. | |
mouse | LDLo | oral | 4gm/kg (4000mg/kg) | LIVER: FATTY LIVER DEGERATION KIDNEY, URETER, AND BLADDER: OTHER CHANGES | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 30(7), Pg. 28, 1965. |
rat | LC50 | inhalation | 20500mg/m3 (20500mg/m3) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) LUNGS, THORAX, OR RESPIRATION: CYANOSIS | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 30(7), Pg. 28, 1965. |
rat | LDLo | oral | 4gm/kg (4000mg/kg) | LIVER: FATTY LIVER DEGERATION KIDNEY, URETER, AND BLADDER: OTHER CHANGES | Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 30(7), Pg. 28, 1965. |
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