Bicyclo[2.2.2]octanon-(2)-p-toluolsulfonylhydrazonn
norbornene
Conditions | Yield |
---|---|
With N,N,N,N,-tetramethylethylenediamine; methyllithium | 99% |
With N,N,N,N,-tetramethylethylenediamine; methyllithium In diethyl ether cooling; | 99 % Chromat. |
norbornene
Conditions | Yield |
---|---|
With lithium triethylborohydride In tetrahydrofuran at 60℃; for 4h; | 83% |
5-(phenylsulfonyl)bicyclo<2.2.2>oct-2-ene
norbornene
Conditions | Yield |
---|---|
With disodium hydrogenphosphate; sodium amalgam In tetrahydrofuran; methanol for 3.5h; | 78.5% |
With sodium amalgam; Na2HPO4 buffer In methanol at -20℃; | 78% |
Conditions | Yield |
---|---|
With lead dioxide at 250℃; |
acetic acid bicyclo[2.2.2]oct-2-yl ester
norbornene
Conditions | Yield |
---|---|
at 400℃; |
Conditions | Yield |
---|---|
With hydrazine hydrate anschliessend Erhitzen mit Kaliumhydroxid und Diaethylenglykol auf 220grad; |
Conditions | Yield |
---|---|
at 250℃; | |
at 280℃; |
Conditions | Yield |
---|---|
at 250℃; under 58840.6 Torr; |
1-phenyl-3-(bicyclo<2.2.2>octan-2-yl)triazene
A
norbornene
exo-bicyclo<3.2.1>octan-2-yl acetate
C
tricyclo<3.2.1.02,7>octane
D
bicyclo<2.2.2>oct-2-yl-acetate
N-(endo-bicyclo<3.2.1>)oct-2-yl-aniline
Conditions | Yield |
---|---|
With sodium acetate; acetic acid Product distribution; Mechanism; deamination reactions of amine via triazene; |
ethyl N-nitroso-N-(bicyclo<3.2.1>octan-2-yl)carbamate
A
norbornene
Bicyclo<3.2.1>oct-2-ene
C
N-(bicyclo<2.2.2>octyl)aniline
D
tricyclo<3.2.1.02,7>octane
E
(1R,3R,5S)-Bicyclo[3.2.1]oct-3-yl-phenyl-amine
N-(exo-bicyclo<3.2.1>oct-2-yl)aniline
Conditions | Yield |
---|---|
With ethanol Product distribution; Mechanism; deamination reactions of amine via nitrosocarbamate; |
S-p-tolyl-S-vinyl-N-(p-tolylsulfonyl)sulfoximine
cyclohexa-1,3-diene
norbornene
Conditions | Yield |
---|---|
With disodium hydrogenphosphate; sodium amalgam 1.) CHCl3, 110 deg C, 50 h 2.) r.t., 75 min; Yield given. Multistep reaction; |
ethyl N-nitroso-N-(exo-bicyclo<3.2.1>octan-2-yl)carbamate
A
norbornene
Bicyclo<3.2.1>oct-2-ene
C
N-(bicyclo<2.2.2>octyl)aniline
D
tricyclo<3.2.1.02,7>octane
E
(1S,3S,5R)-Bicyclo[3.2.1]oct-3-yl-phenyl-amine
N-(exo-bicyclo<3.2.1>oct-2-yl)aniline
Conditions | Yield |
---|---|
With ethanol Product distribution; Mechanism; deamination reactions of amine via nitrosocarbamate; |
norbornene
Conditions | Yield |
---|---|
With potassium hydroxide In ethanol; acetonitrile Ambient temperature; electrolysis: C-anode, Pt-catode; | 74 % Chromat. |
norbornene
Conditions | Yield |
---|---|
With methyl iodide In gas at 100℃; |
Conditions | Yield |
---|---|
at 250℃; |
A
norbornene
Conditions | Yield |
---|---|
With potassium hydroxide |
2-methylenebicyclo[2.2.1]heptane
A
norbornene
Conditions | Yield |
---|---|
at 250℃; |
Conditions | Yield |
---|---|
With pyrographite at -196.15℃; |
Conditions | Yield |
---|---|
With methyllithium at 65℃; |
Conditions | Yield |
---|---|
at 25℃; Photolysis; |
bicyclo[4.2.0]oct-2-ene
norbornene
Conditions | Yield |
---|---|
at 300℃; Kinetics; |
bicyclo[4.2.0]oct-2-ene
A
ethene
B
norbornene
C
cyclohexa-1,3-diene
Conditions | Yield |
---|---|
at 275℃; Kinetics; Further Variations:; Temperatures; |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 0.99 g / methanol 2: 99 percent Chromat. / MeLi; TMEDA / diethyl ether / cooling View Scheme | |
Multi-step reaction with 2 steps 1: 68 percent / methanol 2: 99 percent / MeLi; TMEDA View Scheme |
bicyclo[2.2.2]oct-5-en-2-one
norbornene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: H2 / Pd/C / ethanol / 2 h 2: 0.99 g / methanol 3: 99 percent Chromat. / MeLi; TMEDA / diethyl ether / cooling View Scheme |
cyclohexa-1,3-diene
norbornene
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 6.9 g / hydroquinone / 90 - 100 °C 2: KOH / dimethylsulfoxide; H2O / 20 h 3: H2 / Pd/C / ethanol / 2 h 4: 0.99 g / methanol 5: 99 percent Chromat. / MeLi; TMEDA / diethyl ether / cooling View Scheme | |
Multi-step reaction with 4 steps 1.2: 17 percent / KOH / H2O; dimethylsulfoxide 2.1: 89 percent / H2 / Pd/C 3.1: 68 percent / methanol 4.1: 99 percent / MeLi; TMEDA View Scheme |
norbornene
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: KOH / dimethylsulfoxide; H2O / 20 h 2: H2 / Pd/C / ethanol / 2 h 3: 0.99 g / methanol 4: 99 percent Chromat. / MeLi; TMEDA / diethyl ether / cooling View Scheme |
(1S,4S)-(-)-bicyclo<2.2.2>oct-5-en-2-one
norbornene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 89 percent / H2 / Pd/C 2: 68 percent / methanol 3: 99 percent / MeLi; TMEDA View Scheme |
5-hydroxybicyclo[2.2.2]oct-2-ene
norbornene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: pyridine 2: 83 percent / LiBEt3H / tetrahydrofuran / 4 h / 60 °C View Scheme |
cyclohexa-1,3-diene
norbornene
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 2.) aq. NaOH, aq. H2O2 / 1.) room temp., 1 h, 2.) THF, 1 h, 50 deg C 2: pyridine 3: 83 percent / LiBEt3H / tetrahydrofuran / 4 h / 60 °C View Scheme |
norbornene
A
3H-benzo-1,2-dithiole
B
3,4,5-Trithia-tricyclo[5.2.2.02,6]undecane
Conditions | Yield |
---|---|
With BPTC In dimethyl sulfoxide at 150℃; for 12h; | A 97% B 98% |
Conditions | Yield |
---|---|
With hydrogen; palladium on activated charcoal In hexane at 20 - 22℃; | 97% |
With magnesium; palladium on activated charcoal In methanol Ambient temperature; | 96% |
With hydrazine hydrate In ethanol for 24h; Reflux; | 42% |
norbornene
(E)-1-iodo-3,3-dimethyl-1-butene
Conditions | Yield |
---|---|
With tetrabutyl-ammonium chloride; potassium formate; palladium diacetate In N,N-dimethyl-formamide at 25℃; for 24h; | 96% |
norbornene
α,α-diphenylbenzenemethanesulfenyl chloride
Conditions | Yield |
---|---|
In dichloromethane for 20h; Ambient temperature; | 87% |
Conditions | Yield |
---|---|
at 75 - 80℃; for 0.5h; | 85.6% |
norbornene
(S)-Bicyclo[2.2.2]oct-2-yl-trichloro-silane
Conditions | Yield |
---|---|
With trichlorosilane; (Ra)-(2'-methoxy-[1,1']-binaphthalenyl-2-yl)-diphenylphosphine; bis(η3-allyl-μ-chloropalladium(II)) at 0℃; for 24h; | 85% |
Conditions | Yield |
---|---|
With palladium diacetate; tetrabutyl-ammonium chloride; triethylamine In N,N-dimethyl-formamide at 100℃; for 48h; | 82% |
cis-bis(acetonitrile)chloronitropalladium(II)
norbornene
[Pd(N(O)OCH(CH(CH2CH2)2CH)CH)Cl]2
Conditions | Yield |
---|---|
In acetone under N2, alkene added to soln. of Pd complex in acetone, reacted for 5-10 min; ppt. sepd., washed with acetone, dried overnight in vac.; | 80% |
[Ir(hydrido)2(acetone)2(triphenylphosphine)2](BF4)
norbornene
Ir(C8H10){(C6H5)3P}2(1+)*BF4(1-)
Conditions | Yield |
---|---|
In dichloromethane reflux, 4h, under N2; the cooled soln. was reduced to 5 mL in vac. and Et2O was added until a solid had pptd., recrystn. from CH2Cl2/Et2O, elem. anal.; | 78% |
norbornene
trans-2,3-dibromobicyclo<2.2.2>octane
Conditions | Yield |
---|---|
With bromine In pyridine; chloroform at -40℃; | 72.3% |
norbornene
bicyclo[2.2.2]octan-2-ol
Conditions | Yield |
---|---|
With dimethylsulfide borane complex; dihydrogen peroxide In diethyl ether | 70% |
With sodium tetrahydroborate; boron trifluoride diethyl etherate In diethylene glycol dimethyl ether |
norbornene
tritylsulfenyl chloride
Conditions | Yield |
---|---|
Ambient temperature; | 65% |
In dichloromethane for 20h; Ambient temperature; | 43% |
Conditions | Yield |
---|---|
palladium(II) acetylacetonate In diethyl ether at -10℃; | 64% |
norbornene
potassium cyanide
tert-Butyl-[(S)-1-((Z)-2-iodo-vinyl)-hexyloxy]-dimethyl-silane
3-[(E)-(S)-3-(tert-Butyl-dimethyl-silanyloxy)-oct-1-enyl]-bicyclo[2.2.2]octane-2-carbonitrile
Conditions | Yield |
---|---|
palladium diacetate; triphenylphosphine In N,N-dimethyl-formamide at 80℃; | 63% |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In N,N-dimethyl-formamide at 105℃; for 24h; | 62% |
Conditions | Yield |
---|---|
In benzene for 40h; Irradiation; | 53% |
Conditions | Yield |
---|---|
With palladium diacetate; tetrabutylammomium bromide; potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h; | 52% |
norbornene
bicyclo<2.2.2>octane-cis-2,3-diol
Conditions | Yield |
---|---|
With potassium permanganate; sodium hydroxide In methanol; water; toluene at 5℃; | 46% |
With potassium permanganate; acetone | |
With pyridine; osmium(VIII) oxide; diethyl ether Behandeln des Reaktionsprodukts mit Mannit und wss. KOH in CH2Cl2; |
Conditions | Yield |
---|---|
With tetrabutyl-ammonium chloride; potassium formate; palladium diacetate In N,N-dimethyl-formamide at 25℃; for 24h; | 39% |
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In N,N-dimethyl-formamide at 80℃; for 24h; | A 18% B 34% C 21% |
norbornene
3,4,5-Trithia-tricyclo[5.2.2.02,6]undecane
Conditions | Yield |
---|---|
With S2 | 15% |
tert-butyl (2E,4Z)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)penta-2,4-dienoate
norbornene
Conditions | Yield |
---|---|
With potassium fluoride; chloro(1,5-cyclooctadiene)rhodium(I) dimer; tri tert-butylphosphoniumtetrafluoroborate In 1,4-dioxane; water at 80℃; for 3h; | 15% |
With potassium fluoride; chloro(1,5-cyclooctadiene)rhodium(I) dimer; tri tert-butylphosphoniumtetrafluoroborate In 1,4-dioxane; water at 80℃; for 3h; Inert atmosphere; | 15% |
Conditions | Yield |
---|---|
With dihydrogen peroxide In methanol; formic acid; water; ethyl acetate | 13% |
With dihydrogen peroxide In methanol; formic acid; water; ethyl acetate | 13% |
With dihydrogen peroxide In methanol; formic acid; water; ethyl acetate | 13% |
Multi-step reaction with 2 steps 1: (i) aq. H2O2, HCO2H, Et2O, (ii) LiAlH4 2: CrO3, aq. H2SO4 / acetone View Scheme |
Conditions | Yield |
---|---|
Stage #1: norbornene; naphthalene-2,6-diamine; 2,6-bis(1-methylethyl)benzaldehyde With boron trifluoride diethyl etherate In dichloromethane for 80h; Reflux; Stage #2: With manganese(IV) oxide In 1,2-dichloro-benzene for 16h; Reflux; | 9% |
Conditions | Yield |
---|---|
With 2,2'-azobis(isobutyronitrile) In benzene for 12h; Heating; | 3% |
Conditions | Yield |
---|---|
tetrakis(triphenylphosphine) palladium(0) In acetonitrile at 80℃; Cycloaddition; | 3% |
The Bicyclo(2,2,2)-2-octene is an organic compound with the formula C8H12. The IUPAC name of this chemical is bicyclo[2.2.2]oct-2-ene. With the CAS registry number 931-64-6, it is also named as 2,2,2-Bicyclo-2-octene.
Physical properties about Bicyclo(2,2,2)-2-octene are: (1)ACD/LogP: 3.31; (2)ACD/LogD (pH 5.5): 3.31; (3)ACD/LogD (pH 7.4): 3.31; (4)ACD/BCF (pH 5.5): 194.03; (5)ACD/BCF (pH 7.4): 194.03; (6)ACD/KOC (pH 5.5): 1511.03; (7)ACD/KOC (pH 7.4): 1511.03; (8)Index of Refraction: 1.506; (9)Molar Refractivity: 34.54 cm3; (10)Molar Volume: 116.2 cm3; (11)Polarizability: 13.69×10-24cm3; (12)Surface Tension: 33.8 dyne/cm; (13)Density: 0.93 g/cm3; (14)Flash Point: 18.5 °C; (15)Enthalpy of Vaporization: 36.01 kJ/mol; (16)Boiling Point: 138.3 °C at 760 mmHg; (17)Vapour Pressure: 8.41 mmHg at 25°C.
Preparation: this chemical can be prepared by 5-benzenesulfonyl-bicyclo[2.2.2]oct-2-ene. This reaction will need reagent 6 percent sodium amalgam, Na2HPO4 and solvent tetrahydrofuran, methanol. The reaction time is 3.5 hours. The yield is about 78.5%.
Uses of Bicyclo(2,2,2)-2-octene: it can be used to produce bicyclo[2.2.2]octane. It will need reagent Raney nickel.
You can still convert the following datas into molecular structure:
(1)SMILES: C\1=C\C2CCC/1CC2
(2)InChI: InChI=1/C8H12/c1-2-8-5-3-7(1)4-6-8/h1-2,7-8H,3-6H2
(3)InChIKey: VIQRCOQXIHFJND-UHFFFAOYAH
(4)Std. InChI: InChI=1S/C8H12/c1-2-8-5-3-7(1)4-6-8/h1-2,7-8H,3-6H2
(5)Std. InChIKey: VIQRCOQXIHFJND-UHFFFAOYSA-N
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