1,7-bis(trimethylsiloxy)bicyclo[5.1.0]octane
1,3-cyclooctanedione
Conditions | Yield |
---|---|
With iron(III) chloride In N,N-dimethyl-formamide at 60℃; for 16h; | 73% |
With iron(III) chloride In N,N-dimethyl-formamide at 60 - 70℃; for 3.25h; | |
With iron(III) chloride In N,N-dimethyl-formamide at 60℃; |
9-oxabicyclo[6.1.0]nonan-2-one
1,3-cyclooctanedione
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); 1,2-bis-(diphenylphosphino)ethane In toluene at 140℃; for 96h; | 52% |
With 4-(1-hydroxy-2-(methylamino)ethyl)-1,2-phenylene bis(2,2-dimethylpropanoate); tetrakis(triphenylphosphine) palladium(0) In toluene at 140℃; for 96h; | 52% |
2-Hydroxy-2-methoxymethyl-cycloheptanone
1,3-cyclooctanedione
Conditions | Yield |
---|---|
With potassium hydrogensulfate at 170 - 180℃; under 20 - 25 Torr; | 51% |
(Z)-cyclooct-2-enone
1,3-cyclooctanedione
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; sodium tetrachloropalladate(II) In water; isopropyl alcohol at 50℃; Wacker-Tsuji oxidation; Inert atmosphere; | 37% |
1-Trimethylsiloxy-bicyclo[5.1.0]octan
A
3-hydroxycyclooctan-1-one
B
1,3-cyclooctanedione
Conditions | Yield |
---|---|
With bis(acetylacetonate)oxovanadium; oxygen In ethanol Ambient temperature; | A 31% B 33% |
With vanadyl acetylacetonate; oxygen In ethanol at 20℃; for 20h; | A 31% B 33% |
cis-cyclooctane-1,3-diol
1,3-cyclooctanedione
Conditions | Yield |
---|---|
With chromium(VI) oxide In acetone |
Conditions | Yield |
---|---|
Multistep reaction; |
Conditions | Yield |
---|---|
(i) Mor, (ii) aq. HCl; Multistep reaction; |
1,2-Bis-(trimethylsiloxy)-cyclohepten-(1)
Bromoform
1,3-cyclooctanedione
Conditions | Yield |
---|---|
solvent: toluene, 0 grad C, 1 hr.; Yield given. Multistep reaction; |
1,3-cyclooctanedione
Conditions | Yield |
---|---|
With chromium(VI) oxide |
1,3-cyclooctanedione
Conditions | Yield |
---|---|
With sulfuric acid In diethyl ether; chloroform |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: 9-BBN / tetrahydrofuran / 48 h / 20 °C 1.2: 76 percent / NaOH; aq. H2O2 / tetrahydrofuran; ethanol / 1 h / Heating 2.1: oxalyl chloride; DMSO; Et3N / CHCl3 / 1 h / -78 - -10 °C 3.1: H2SO4 / diethyl ether; CHCl3 View Scheme | |
Multi-step reaction with 2 steps 1: pyridinium p-toluenesulfonate / water; acetone / Reflux; Inert atmosphere 2: tert.-butylhydroperoxide; sodium tetrachloropalladate(II) / water; isopropyl alcohol / 50 °C / Inert atmosphere View Scheme |
1,4-dioxaspiro[4,7]dodecan-7-ol
1,3-cyclooctanedione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: oxalyl chloride; DMSO; Et3N / CHCl3 / 1 h / -78 - -10 °C 2: H2SO4 / diethyl ether; CHCl3 View Scheme |
1,2-Bis-(trimethylsiloxy)-cyclohepten-(1)
1,3-cyclooctanedione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: Et2Zn / toluene / 2.25 h / Ambient temperature 2: FeCl3 / dimethylformamide / 3.25 h / 60 - 70 °C View Scheme | |
Multi-step reaction with 2 steps 1: 97 percent / diethylzinc / toluene / 16 h / Ambient temperature 2: 73 percent / FeCl3 / dimethylformamide / 16 h / 60 °C View Scheme | |
Multi-step reaction with 2 steps 1: 48 percent / Zn/Cu-(CH3)2CHI / CH2Cl2 / 1.) 0 deg C, 1 h, 2.) room temperature, 2 h 2: 51 percent / potassium hydrogen sulfate / 170 - 180 °C / 20 - 25 Torr View Scheme | |
Multi-step reaction with 2 steps 1: diethylzinc / toluene 2: iron(III) chloride / N,N-dimethyl-formamide / 60 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: Na sand / toluene / Heating 2: Et2Zn / toluene / 2.25 h / Ambient temperature 3: FeCl3 / dimethylformamide / 3.25 h / 60 - 70 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 96 percent / Na / toluene / 96 h / Heating 2: 97 percent / diethylzinc / toluene / 16 h / Ambient temperature 3: 73 percent / FeCl3 / dimethylformamide / 16 h / 60 °C View Scheme | |
Multi-step reaction with 2 steps 1: Na / toluene / 96 h 2: solvent: toluene, 0 grad C, 1 hr. View Scheme |
1,3-cyclooctanedione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: LiAlH4 / diethyl ether 2: CrO3 / acetone View Scheme |
(Z)-Cyclooctene
1,3-cyclooctanedione
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: Br2 / CCl4 2: Mor / toluene / Heating 3: NBS, AIBN, CaCO3 / CCl4 4: acetic acid 5: KOH / methanol / Ambient temperature 6: NBS, Py / CCl4 / Heating 7: (i) Mor, (ii) aq. HCl View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: PCl3, benzene-1,2-diol / Heating 2: NBS, AIBN, CaCO3 / CCl4 View Scheme | |
Multi-step reaction with 5 steps 1: hydrogenchloride; bromine / ethanol; water / 72 h / 0 °C / Inert atmosphere 2: toluene-4-sulfonic acid / benzene / 24 h / Reflux; Inert atmosphere 3: 1,8-diazabicyclo[5.4.0]undec-7-ene / 3 h / 160 °C / Inert atmosphere 4: pyridinium p-toluenesulfonate / water; acetone / Reflux; Inert atmosphere 5: tert.-butylhydroperoxide; sodium tetrachloropalladate(II) / water; isopropyl alcohol / 50 °C / Inert atmosphere View Scheme |
(E)-1-Bromo-cyclooctene
1,3-cyclooctanedione
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: NBS, AIBN, CaCO3 / CCl4 2: acetic acid 3: KOH / methanol / Ambient temperature 4: NBS, Py / CCl4 / Heating 5: (i) Mor, (ii) aq. HCl View Scheme |
1,2-dibromocyclooctane
1,3-cyclooctanedione
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: Mor / toluene / Heating 2: NBS, AIBN, CaCO3 / CCl4 3: acetic acid 4: KOH / methanol / Ambient temperature 5: NBS, Py / CCl4 / Heating 6: (i) Mor, (ii) aq. HCl View Scheme |
(E)-1-Chloro-cyclooctene
1,3-cyclooctanedione
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: NBS, AIBN, CaCO3 / CCl4 View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: NBS, Py / CCl4 / Heating 2: (i) Mor, (ii) aq. HCl View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: acetic acid 2: KOH / methanol / Ambient temperature 3: NBS, Py / CCl4 / Heating 4: (i) Mor, (ii) aq. HCl View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: KOH / methanol / Ambient temperature 2: NBS, Py / CCl4 / Heating 3: (i) Mor, (ii) aq. HCl View Scheme |
2-bromocyclooctan-1-one
1,3-cyclooctanedione
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: toluene-4-sulfonic acid / benzene / 24 h / Reflux; Inert atmosphere 2: 1,8-diazabicyclo[5.4.0]undec-7-ene / 3 h / 160 °C / Inert atmosphere 3: pyridinium p-toluenesulfonate / water; acetone / Reflux; Inert atmosphere 4: tert.-butylhydroperoxide; sodium tetrachloropalladate(II) / water; isopropyl alcohol / 50 °C / Inert atmosphere View Scheme |
2-Brom-1-cyclooctanon-ethylenacetal
1,3-cyclooctanedione
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1,8-diazabicyclo[5.4.0]undec-7-ene / 3 h / 160 °C / Inert atmosphere 2: pyridinium p-toluenesulfonate / water; acetone / Reflux; Inert atmosphere 3: tert.-butylhydroperoxide; sodium tetrachloropalladate(II) / water; isopropyl alcohol / 50 °C / Inert atmosphere View Scheme |
Isopropenyl acetate
1,3-cyclooctanedione
1,3-diacetoxy-1,3-cyclooctadiene
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid at 90℃; | 99% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone Ambient temperature; | 97% |
With potassium carbonate In N,N-dimethyl-formamide; acetone for 30h; Heating; | 97% |
Conditions | Yield |
---|---|
Stage #1: 1,3-cyclooctanedione With N,N,N,N,N,N-hexamethylphosphoric triamide In tetrahydrofuran at 0℃; deprotonation; Stage #2: chloro-trimethyl-silane In tetrahydrofuran at 0℃; silylation; Further stages.; | 76% |
With N,N,N,N,N,N-hexamethylphosphoric triamide; diisopropylamine; lithium diisopropyl amide In tetrahydrofuran; hexane at 0℃; for 3h; | 76% |
1,3-cyclooctanedione
2,2-difluoro-1,3-cyclooctanedione
Conditions | Yield |
---|---|
With caesium carbonate; Selectfluor In acetonitrile at 0 - 20℃; Inert atmosphere; | 73% |
Stage #1: 1,3-cyclooctanedione With caesium carbonate In acetonitrile at 0℃; for 0.25h; Inert atmosphere; Stage #2: With Selectfluor In acetonitrile at 0 - 20℃; for 6.25h; | 69% |
Stage #1: 1,3-cyclooctanedione With caesium carbonate In acetonitrile at 20℃; for 0.5h; Inert atmosphere; Stage #2: With Selectfluor In acetonitrile at 20℃; for 1.5h; Cooling with ice; Inert atmosphere; | 31.1% |
Ketene
1,3-cyclooctanedione
A
Acetic acid (E)-3-oxo-cyclooct-1-enyl ester
B
1,3-diacetoxy-1,3-cyclooctadiene
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid at 125℃; for 10h; | A 8% B 57% |
Conditions | Yield |
---|---|
With piperidine; acetic acid In toluene Ambient temperature; | 56% |
Conditions | Yield |
---|---|
With iodine; tetrabutylammoniun azide; 4-pyrrolidin-1-ylpyridine In tetrahydrofuran at 20℃; for 12h; | 51% |
Conditions | Yield |
---|---|
With potassium carbonate In dimethyl sulfoxide at 30℃; for 11.1667h; | A 24% B 14% |
1,3-cyclooctanedione
<2,2,4,4,8,8-D6>-Cyclo-octan-1,3-dion
Conditions | Yield |
---|---|
With water-d2 |
1,3-cyclooctanedione
4-chloro-aniline
2-(p-Chlor-phenylhydrazono)-cyclooctandion-(1,3)
Conditions | Yield |
---|---|
(i) NaNO2, aq. H2SO4, (ii) /BRN= 2354368/, NaOAc; Multistep reaction; |
Conditions | Yield |
---|---|
(i) NaNO2, aq. HCl, (ii) /BRN= 2354368/, NaOAc; Multistep reaction; |
3-phenylbut-3-en-1-yl 4-methylbenzenesulfonate
1,3-cyclooctanedione
3-<(3-phenyl-3-butenyl)oxy>-2-cycloocten-1-one
Conditions | Yield |
---|---|
With potassium hexamethylsilazane 1.) DME, toluene; 0 deg. C , 30 min. 2.) DME, toluene; 60 deg. C ,16h; Yield given. Multistep reaction; |
1,3-cyclooctanedione
but-3-enyl 4-methylbenzenesulfonate
3-(3-butenyloxy)-2-cycloocten-1-one
Conditions | Yield |
---|---|
With potassium tert-butylate 2.) DME, 60 degC, 16 h; Yield given. Multistep reaction; | |
With tert-butoxide 1.) DME, -10 deg. C, 40 min. 2.) DME, 60 deg. C, 24h; Yield given. Multistep reaction; |
1,3-cyclooctanedione
4-methylpent-3-enyl 4-methylbenzenesulfonate
3-<(4-methyl-3-pentenyl)oxy>-2-cycloocten-1-one
Conditions | Yield |
---|---|
With potassium tert-butylate 60 degC, 16 h; Yield given. Multistep reaction; | |
With potassium hexamethylsilazane 1.) DME, toluene; 0 deg. C , 30 min. 2.) DME, toluene; 60 deg. C ,16h; Yield given. Multistep reaction; |
1,3-cyclooctanedione
4-phenyl-3-butenyl para-toluenesulfonate
3-<((E)-4-phenyl-3-butenyl)oxy>-2-cycloocten-1-one
Conditions | Yield |
---|---|
With potassium tert-butylate 60 deg C, 16 h; Yield given. Multistep reaction; | |
With tert-butoxide 1.) DME, -10 deg. C, 40 min. 2.) DME, 60 deg. C, 24h; Yield given. Multistep reaction; |
1,3-cyclooctanedione
(±)-2-methylbut-3-en-1-yl 4-methylbenzenesulfonate
3-<(2-methyl-3-butenyl)oxy>-2-cycloocten-1-one
Conditions | Yield |
---|---|
With tert-butoxide 1.) DME, -10 deg. C, 40 min. 2.) DME, 60 deg. C, 24h; Yield given. Multistep reaction; |
1,3-cyclooctanedione
(E)-hexa-3,5-dien-1-yl 4-methylbenzenesulfonate
3-<(E)-3,5-hexadienyloxy>-2-cycloocten-1-one
Conditions | Yield |
---|---|
With potassium tert-butylate 2.) DME, 60 deg C, 16 h; Yield given. Multistep reaction; |
1,3-cyclooctanedione
triethyloxonium fluoroborate
3-(ethoxy)-2-cycloocten-1-one
Conditions | Yield |
---|---|
With potassium tert-butylate 1.) DME, 60 min, 2.) DME,CH2Cl2, 30 min; Yield given. Multistep reaction; |
1,3-cyclooctanedione
Toluene-4-sulfonic acid (E)-5-trimethylsilanyl-pent-3-enyl ester
3-<<(E)-5-(trimethylsilyl)-3-pentenyl>oxy>-2-cycloocten-1-one
Conditions | Yield |
---|---|
With tert-butoxide 1.) DME, -10 deg. C, 40 min. 2.) DME, 60 deg. C, 24h; Yield given. Multistep reaction; |
1,3-cyclooctanedione
(Z)-hexa-3,5-dienyl p-toluenesulfonate
3-<(E)-3,5-hexadienyloxy>-2-cycloocten-1-one
Conditions | Yield |
---|---|
With tert-butoxide 1.) DME, -10 deg. C, 40 min. 2.) DME, 60 deg. C, 24h; Yield given. Multistep reaction; |
1,3-cyclooctanedione
Toluene-4-sulfonic acid (E)-2-methyl-hexa-3,5-dienyl ester
3-<((E)-2-methyl-3,5-hexadienyl)oxy>-2-cycloocten-1-one
Conditions | Yield |
---|---|
With tert-butoxide 1.) DME, -10 deg. C, 40 min. 2.) DME, 60 deg. C, 24h; Yield given. Multistep reaction; |
1,3-cyclooctanedione
3-heptenyl toluenesulfonate
3-<(E)-3-heptenyloxy>-2-cycloocten-1-one
Conditions | Yield |
---|---|
With potassium tert-butylate 60 deg C, 16 h; Yield given. Multistep reaction; | |
With potassium hexamethylsilazane 1.) DME, toluene; 0 deg. C , 30 min. 2.) DME, toluene; 60 deg. C ,16h; Yield given. Multistep reaction; |
The CAS registry number of Cyclooctane-1,3-dione is 935-29-5. This chemical's molecular formula is C8H12O2 and molecular weight is 140.1797. Its systematic name is called cyclooctane-1,3-dione.
Physical properties of Cyclooctane-1,3-dione: (1)ACD/LogP: -0.07; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 22; (5)ACD/KOC (pH 7.4): 22; (6)#H bond acceptors: 2; (7)Index of Refraction: 1.463; (8)Molar Refractivity: 37.155 cm3; (9)Molar Volume: 134.926 cm3; (10)Surface Tension: 36.296 dyne/cm; (11)Density: 1.039 g/cm3; (12)Flash Point: 98.996 °C; (13)Enthalpy of Vaporization: 50.54 kJ/mol; (14)Boiling Point: 267.379 °C at 760 mmHg; (15)Vapour Pressure: 0.008 mmHg at 25°C.
You can still convert the following datas into molecular structure:
(1)SMILES: O=C1CC(=O)CCCCC1
(2)InChI: InChI=1/C8H12O2/c9-7-4-2-1-3-5-8(10)6-7/h1-6H2
(3)InChIKey: OOOLFZKAFMJAJK-UHFFFAOYAH
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