cyclohex-1-en-1-yl trifluoromethane sulfonate
1-bromocyclohex-1-ene
Conditions | Yield |
---|---|
With tris(2,4-pentanedionato)ruthenium(III); 1,10-Phenanthroline; ethylmagnesium bromide; lithium bromide In tetrahydrofuran at 60℃; for 24h; Inert atmosphere; | 91% |
Conditions | Yield |
---|---|
With 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one; triphenylphosphine In dichloromethane at 40℃; for 24h; | 75% |
With triphenyl phosphite; bromine; triethylamine In dichloromethane at -60 - 20℃; for 20h; Inert atmosphere; Reflux; | 67% |
With 2,4,4,6-Tetrabromo-2,5-cyclohexadien-1-one; triphenylphosphine In dichloromethane for 18h; Reflux; Inert atmosphere; |
Conditions | Yield |
---|---|
With pyridine; phosphorus tribromide In tetrahydrofuran at -10 - -5℃; for 10h; Large scale; | 72% |
Conditions | Yield |
---|---|
Stage #1: cyclohexene-1-carboxylic acid With bromine In dichloromethane at 20℃; for 0.5h; Stage #2: With sulfolane; dmap at 40 - 90℃; | 66% |
Conditions | Yield |
---|---|
With morpholine; dimethyl sulfoxide In benzene for 40h; Heating; | 65% |
Conditions | Yield |
---|---|
With sodium amide; tert-butyl alcohol In tetrahydrofuran 1.) -40 deg C, 1 h, 2.) RT, 1 h; | 63% |
With quinoline |
Conditions | Yield |
---|---|
With N-Bromosuccinimide; tetrabutylammomium bromide; potassium carbonate In 1,4-dioxane at 90℃; Inert atmosphere; regioselective reaction; | 58% |
With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; 1,2-dibromo-1,1,2,2-tetrafluoroethane 1.) a.) hexane, -78 deg C, 2 h, b.) RT, 3 h, 2.) -78 deg C, 1 h; Yield given. Multistep reaction; |
trans-1-bromo-2-fluorocyclohexane
1-bromocyclohex-1-ene
Conditions | Yield |
---|---|
With sodium amide In tetrahydrofuran; tert-butyl alcohol | 47% |
Conditions | Yield |
---|---|
With oxalyl dichloride; Triphenylphosphine oxide; lithium bromide In chloroform at 20℃; for 7h; Appel reaction; | 14% |
dibromo-cyclohexane
1-bromocyclohex-1-ene
Conditions | Yield |
---|---|
With quinoline |
Conditions | Yield |
---|---|
With pyridine; bromine In chloroform |
Conditions | Yield |
---|---|
(i) Li, Na, Et2O, (ii) Br2, pentane; Multistep reaction; |
2,2,2-trifluoroethanol
cyclohex-1-en-1-yl trifluoromethane sulfonate
A
1-bromocyclohex-1-ene
B
cyclohexanone
C
1,1-Bis(2,2,2-trifluorethoxy)cyclohexan
Conditions | Yield |
---|---|
With tetraethylammonium bromide; triethylamine at 135℃; for 360h; Product distribution; Mechanism; | A 30 % Chromat. B 60 % Chromat. C 10 % Chromat. |
(+-)-trans-1-bromo-2-chloro-cyclohexane
A
1-bromocyclohex-1-ene
B
1-chlorocyclohexene
Conditions | Yield |
---|---|
With potassium tert-butylate In tert-butyl alcohol at 50℃; for 120h; Yield given. Yields of byproduct given; | |
With sodium amide; sodium t-butanolate In tetrahydrofuran for 2h; Product distribution; Mechanism; Ambient temperature; var. NaNH2-Na(anion), var. product distributions; | |
With 15-crown-5; sodium amide; sodium t-butanolate In tetrahydrofuran for 0.5h; Product distribution; Mechanism; Ambient temperature; |
Conditions | Yield |
---|---|
With sodium amide; sodium 3-methyl-pentoxide-3 In tetrahydrofuran at 25℃; Title compound not separated from byproducts; | A 69 % Chromat. B 29 % Chromat. |
With sodium amide; sodium 3-methyl-pentoxide-3 In tetrahydrofuran at 25℃; Product distribution; var. complex bases; |
trans-1-bromo-2-fluorocyclohexane
A
1-bromocyclohex-1-ene
B
3-methoxycyclohexene
C
3-fluorocyclohex-1-ene
D
cyclohexa-1,3-diene
Conditions | Yield |
---|---|
With potassium tert-butylate for 3h; Product distribution; Heating; dehydrohalogenation with different equivalents of various bases at different temperatures and reaction times; |
Conditions | Yield |
---|---|
With phenyl(tribromomethyl)mercury(II) In benzene at 75 - 80℃; for 2h; | |
With phosphorus pentabromide In sulfolane at 30 - 80℃; for 6h; Inert atmosphere; |
Conditions | Yield |
---|---|
at 30℃; Rate constant; | |
at 50℃; Rate constant; | |
at 20℃; Rate constant; |
2-bromocyclocyclohexanol
1-bromocyclohex-1-ene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 66.6 percent / diethylaminosulfur trifluoride / CH2Cl2 / 1.5 h / -78 °C 2: 47 percent / sodamide / 2-methyl-propan-2-ol; tetrahydrofuran View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 86.95 percent / hydrogen fluoride, N-bromoacetamide / diethyl ether / 1.5 h / 1.) dry ice bath; 2.) room temperature overnight 2: 47 percent / sodamide / 2-methyl-propan-2-ol; tetrahydrofuran View Scheme |
methyl cyclohex-1-ene-1-carboxylate
1-bromocyclohex-1-ene
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: potassium hydroxide / dichloromethane; water / 20 °C 2.1: bromine / dichloromethane / 0.5 h / 20 °C 2.2: 40 - 90 °C View Scheme |
1-bromocyclohex-1-ene
bis(pinacol)diborane
2-(cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Conditions | Yield |
---|---|
With triphenylphosphine; bis(triphenylphosphine)palladium(II) chloride In toluene mixt. in toluene stirred at 50°C for 5 h; treated (H2O) at room temp.; extd. (benzene); washed with brine; dried (MgSO4); purified by chromy. on silica gel or by distn. (vac.); | 99% |
With bis-triphenylphosphine-palladium(II) chloride; potassium phenolate; triphenylphosphine In toluene at 50℃; for 5h; Inert atmosphere; | 85% |
With trans-bis(triphenylphosphine)palladium dichloride; potassium phenolate; triphenylphosphine In toluene at 50℃; for 5h; Inert atmosphere; | 85% |
1-bromocyclohex-1-ene
N1,N5-dimethoxy-N1,N5-dimethylglutaramide
1,5-di(cyclohex-1-en-1-yl)pentane-1,5-dione
Conditions | Yield |
---|---|
Stage #1: 1-bromocyclohex-1-ene With chloro-trimethyl-silane; magnesium; ethylene dibromide; lithium chloride In tetrahydrofuran Inert atmosphere; Reflux; Schlenk technique; Stage #2: N1,N5-dimethoxy-N1,N5-dimethylglutaramide In tetrahydrofuran; diethyl ether at 23℃; Inert atmosphere; Schlenk technique; Cooling; | 99% |
1-bromocyclohex-1-ene
(4R,5R)-N,N'-dimethoxy-N,N',2,2-tetramethyl-1,3-dioxolane-4,5-dicarboxamide
Conditions | Yield |
---|---|
Stage #1: 1-bromocyclohex-1-ene With chloro-trimethyl-silane; magnesium; ethylene dibromide; lithium chloride In tetrahydrofuran Inert atmosphere; Reflux; Schlenk technique; Stage #2: (4R,5R)-N,N'-dimethoxy-N,N',2,2-tetramethyl-1,3-dioxolane-4,5-dicarboxamide In tetrahydrofuran; diethyl ether at 23℃; Inert atmosphere; Schlenk technique; Cooling; | 99% |
Conditions | Yield |
---|---|
With tetrabutylammomium bromide; dicobalt octacarbonyl In sodium hydroxide; benzene at 65℃; for 2.5h; Irradiation; | 98% |
1-bromocyclohex-1-ene
Conditions | Yield |
---|---|
Stage #1: 1-bromocyclohex-1-ene With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 0.5h; Inert atmosphere; Stage #2: (R)-2-(4-(4-methoxyphenyl)butan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran; pentane at -78 - 0℃; for 0.5h; Inert atmosphere; Stage #3: With iodine; sodium methylate In tetrahydrofuran; methanol; pentane at -78 - 0℃; for 0.5h; Inert atmosphere; | 98% |
1-bromocyclohex-1-ene
dibutyltin chloride
dibutylbis(cyclohexen-1-yl)stannane
Conditions | Yield |
---|---|
With lithium In diethyl ether Ar atmosphere, addn. of soln. of Bu2SnCl2 to soln. of alkenyllithium (1 h), stirring (reflux, 12 h); hydrolysis (saturated aq. NH4Cl), extn. (Et2O), drying of organic phases(MgSO4), removement of solvent, fractional distillation; elem. anal.; | 96% |
1-bromocyclohex-1-ene
tributyltin chloride
tri-n-butyl-(1-cyclohex-1-enyl)-stannane
Conditions | Yield |
---|---|
Stage #1: 1-bromocyclohex-1-ene With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 1h; Inert atmosphere; Stage #2: tributyltin chloride In tetrahydrofuran; pentane at -78 - 20℃; for 18h; Inert atmosphere; | 96% |
1-bromocyclohex-1-ene
(E)-3-methyl-1-phenylbut-3-en-1-one oxime
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); (R)-N-((S)-(2-(di((3R,5R,7R)-adamantan-1-yl)phosphaneyl)-4,5-dimethoxyphenyl)(phenyl)methyl)-N,2-dimethylpropane-2-sulfinamide; sodium t-butanolate In toluene at 65℃; for 12h; Inert atmosphere; Schlenk technique; enantioselective reaction; | 95% |
1-bromocyclohex-1-ene
potassium 2-nitro-5-methoxylbenzoate
2-cyclohexenyl-4-methoxy-1-nitrobenzene
Conditions | Yield |
---|---|
With 1,10-Phenanthroline; palladium(II) hexafluoroacetylacetonate; tri-1-napthylphosphine; copper(l) chloride In 1-methyl-pyrrolidin-2-one; 1,3,5-trimethyl-benzene at 130℃; for 16h; Inert atmosphere; regiospecific reaction; | 94% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 0℃; for 2h; | 93% |
1-bromocyclohex-1-ene
N'-methyl-N'-phenylacetohydrazide
9-methyl-2,3,4,9-tetrahydro-1H-carbazole
Conditions | Yield |
---|---|
Stage #1: 1-bromocyclohex-1-ene; N'-methyl-N'-phenylacetohydrazide With copper(l) iodide; potassium carbonate; N,N-dimethylethylenediamine In toluene at 110℃; for 24h; Fischer Indole Synthesis; Schlenk technique; Inert atmosphere; Stage #2: With zinc(II) chloride In toluene at 90℃; for 1h; Fischer Indole Synthesis; | 93% |
1-bromocyclohex-1-ene
N'-(4-fluorophenyl)-N'-methylacetohydrazide
6-fluoro-9-methyl-2,3,4,9-tetrahydro-1H-carbazole
Conditions | Yield |
---|---|
Stage #1: 1-bromocyclohex-1-ene; N'-(4-fluorophenyl)-N'-methylacetohydrazide With copper(l) iodide; potassium carbonate; N,N-dimethylethylenediamine In toluene at 110℃; for 24h; Fischer Indole Synthesis; Schlenk technique; Inert atmosphere; Stage #2: With zinc(II) chloride In toluene at 90℃; for 1h; Fischer Indole Synthesis; | 92% |
1-bromocyclohex-1-ene
(E)-2-methyl-3-(thiophen-2-yl)acrylaldehyde
(E)-1-cyclohexenyl-2-methyl-3-(thiophen-2-yl)prop-2-en-1-ol
Conditions | Yield |
---|---|
Stage #1: 1-bromocyclohex-1-ene With tert.-butyl lithium In diethyl ether; pentane at -78 - 20℃; for 1.25h; Stage #2: (E)-2-methyl-3-(thiophen-2-yl)acrylaldehyde In diethyl ether; pentane at -78 - 0℃; for 1h; | 92% |
1-bromocyclohex-1-ene
potassium o-nitrobenzoate
1-cyclohexenyl-2-nitrobenzene
Conditions | Yield |
---|---|
With 1,10-Phenanthroline; palladium(II) hexafluoroacetylacetonate; tri-1-napthylphosphine; copper(l) chloride In 1-methyl-pyrrolidin-2-one; 1,3,5-trimethyl-benzene at 130℃; for 16h; Reagent/catalyst; Temperature; Solvent; Inert atmosphere; regiospecific reaction; | 92% |
1-bromocyclohex-1-ene
cyclobutanone
1-(cyclohex-1-en-1-yl)cyclobutan-1-ol
Conditions | Yield |
---|---|
Stage #1: 1-bromocyclohex-1-ene With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 0.5h; Inert atmosphere; Stage #2: cyclobutanone In tetrahydrofuran; pentane at -78℃; for 0.5h; Inert atmosphere; | 92% |
1-bromocyclohex-1-ene
2-methylbut-2-enal
(E)-1-cyclohexenyl-2-methylbut-2-en-1-ol
Conditions | Yield |
---|---|
Stage #1: 1-bromocyclohex-1-ene With tert.-butyl lithium In diethyl ether; pentane at -78 - 20℃; for 1.25h; Stage #2: 2-methylbut-2-enal In diethyl ether; pentane at -78 - 0℃; for 1h; | 91% |
1-bromocyclohex-1-ene
Conditions | Yield |
---|---|
Stage #1: 1-bromocyclohex-1-ene With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 1h; Stage #2: 4-{[tert-butyl(dimethyl)silyl]oxy}-1-(5-{[(triisopropylsilyl)oxy]methyl}-3-thienyl)butan-1-one With lanthanium (III) chloride bis(lithium chloride) complex In tetrahydrofuran; pentane for 1h; | 91% |
1-bromocyclohex-1-ene
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 70℃; for 7h; | 90% |
1-bromocyclohex-1-ene
(2-cyclohexylidene ethenyl)-benzene
Conditions | Yield |
---|---|
Stage #1: (2-cyclohexylidene ethenyl)-benzene With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 0.5h; Schlenk technique; Inert atmosphere; Stage #2: 1-bromocyclohex-1-ene With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; bis(dibenzylideneacetone)-palladium(0) In toluene at 40℃; for 1h; Schlenk technique; Inert atmosphere; | 90% |
1-bromocyclohex-1-ene
N'-(4-chlorophenyl)-N'-methylacetohydrazide
6-chloro-9-methyl-2,3,4,9-tetrahydro-1H-carbazole
Conditions | Yield |
---|---|
Stage #1: 1-bromocyclohex-1-ene; N'-(4-chlorophenyl)-N'-methylacetohydrazide With copper(l) iodide; potassium carbonate; N,N-dimethylethylenediamine In toluene at 110℃; for 24h; Fischer Indole Synthesis; Schlenk technique; Inert atmosphere; Stage #2: With zinc(II) chloride In toluene at 90℃; for 1h; Fischer Indole Synthesis; | 89% |
1-bromocyclohex-1-ene
9-benzyl-2,3,4,9-tetrahydro-1H-carbazole
Conditions | Yield |
---|---|
Stage #1: 1-bromocyclohex-1-ene; N'-benzyl-N'-phenylacetohydrazide With copper(l) iodide; potassium carbonate; N,N-dimethylethylenediamine In toluene at 110℃; for 24h; Fischer Indole Synthesis; Schlenk technique; Inert atmosphere; Stage #2: With zinc(II) chloride In toluene at 90℃; for 1h; Fischer Indole Synthesis; | 89% |
1-bromocyclohex-1-ene
C11H14N2O
N-allyl-1,2,3,4-tetrahydrocarbazole
Conditions | Yield |
---|---|
Stage #1: 1-bromocyclohex-1-ene; C11H14N2O With copper(l) iodide; potassium carbonate; N,N-dimethylethylenediamine In toluene at 110℃; for 24h; Fischer Indole Synthesis; Schlenk technique; Inert atmosphere; Stage #2: With zinc(II) chloride In toluene at 90℃; for 1h; Fischer Indole Synthesis; | 88% |
1-bromocyclohex-1-ene
(E)-3-(4-methylphenyl)-2-methylacrylaldehyde
(E)-1-cyclohexenyl-2-methyl-3-p-tolylprop-2-en-1-ol
Conditions | Yield |
---|---|
Stage #1: 1-bromocyclohex-1-ene With tert.-butyl lithium In diethyl ether; pentane at -78 - 20℃; for 1.25h; Stage #2: (E)-3-(4-methylphenyl)-2-methylacrylaldehyde In diethyl ether; pentane at -78 - 0℃; for 1h; | 88% |
1-bromocyclohex-1-ene
3-ethoxy-6-methylcyclohex-2-en-1-one
Conditions | Yield |
---|---|
Stage #1: 3-ethoxy-6-methylcyclohex-2-en-1-one With lithium hexamethyldisilazane In toluene at -20℃; for 0.5h; Inert atmosphere; Stage #2: 1-bromocyclohex-1-ene With chloro[(tri-tert-butylphosphine)-2-(2-aminobiphenyl)]palladium (II) In toluene at -20 - 20℃; for 4.16667h; Inert atmosphere; Schlenk technique; | 88% |
1-bromocyclohex-1-ene
2-(4-(4-methoxyphenyl)butan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Conditions | Yield |
---|---|
Stage #1: 1-bromocyclohex-1-ene With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 0.5h; Inert atmosphere; Stage #2: 2-(4-(4-methoxyphenyl)butan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran; pentane at -78 - 0℃; for 0.5h; Inert atmosphere; Stage #3: With iodine; sodium methylate In tetrahydrofuran; methanol; pentane at -78 - 0℃; for 0.5h; Inert atmosphere; | 87% |
1-bromocyclohex-1-ene
bis(pinacol)diborane
2-(cyclohex-2-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
Conditions | Yield |
---|---|
With chlorotris(triphenylphosphine)cobalt(I); sodium ethanolate; 1,3-dicyclohexylimidazol-2-ylidene In tert-butyl methyl ether at 50℃; for 16h; Inert atmosphere; | 87% |
1-bromocyclohex-1-ene
N'-(4-methoxyphenyl)-N'-methylacetohydrazide
6-methoxy-9-methyl-2,3,4,9-tetrahydro-1H-carbazole
Conditions | Yield |
---|---|
Stage #1: 1-bromocyclohex-1-ene; N'-(4-methoxyphenyl)-N'-methylacetohydrazide With copper(l) iodide; potassium carbonate; N,N-dimethylethylenediamine In toluene at 110℃; for 24h; Fischer Indole Synthesis; Schlenk technique; Inert atmosphere; Stage #2: With zinc(II) chloride In toluene at 90℃; for 1h; Fischer Indole Synthesis; | 86% |
1-bromocyclohex-1-ene
methyloxirane
1-(cyclohex-1-en-1-yl)propan-2-ol
Conditions | Yield |
---|---|
With pyridine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 4,4'-bipyridine; NiI2*3.9H2O; triethylamine hydrochloride; sodium iodide; zinc at 20℃; for 12h; | 86% |
1-bromocyclohex-1-ene
potassium 2-nitro-3-methylbenzoate
1-cyclohexenyl-3-methyl-2-nitrobenzene
Conditions | Yield |
---|---|
With 1,10-Phenanthroline; palladium(II) hexafluoroacetylacetonate; tri-1-napthylphosphine; copper(l) chloride In 1-methyl-pyrrolidin-2-one; 1,3,5-trimethyl-benzene at 130℃; for 16h; Inert atmosphere; regiospecific reaction; | 86% |
The 1-Bromo-1-cyclohexene, with the CAS registry number 2044-08-8.It belongs to the product Organic matters. This chemical's molecular formula is C6H9Br and molecular weight is 161.03. What's more, Its systematic name is 1-Bromocyclohexene.
Physical properties about 1-Bromo-1-cyclohexene are: (1)ACD/LogP: 3.076; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.08; (4)ACD/LogD (pH 7.4): 3.08; (5)ACD/BCF (pH 5.5): 128.19; (6)ACD/BCF (pH 7.4): 128.19; (7)ACD/KOC (pH 5.5): 1123.05; (8)ACD/KOC (pH 7.4): 1123.05; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Index of Refraction: 1.538; (13)Molar Refractivity: 35.056 cm3; (14)Molar Volume: 112.101 cm3; (15)Surface Tension: 37.5029983520508 dyne/cm; (16)Density: 1.437 g/cm3; (17)Flash Point: 58.157 °C; (18)Enthalpy of Vaporization: 38.52 kJ/mol; (19)Boiling Point: 165.211 °C at 760 mmHg; (20)Vapour Pressure: 2.48900008201599 mmHg at 25°C;
You can still convert the following datas into molecular structure:
(1)SMILES:Br\C1=C\CCCC1;
(2)Std. InChI:InChI=1S/C6H9Br/c7-6-4-2-1-3-5-6/h4H,1-3,5H2;
(3)Std. InChIKey:QBUMXSSCYUMVAW-UHFFFAOYSA-N.
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